RSS-Feed abonnieren
DOI: 10.1055/s-2003-42460
Electron-Rich Phosphines in Organic Synthesis II. Catalytic Applications
Publikationsverlauf
Publikationsdatum:
06. November 2003 (online)

Abstract
A literature survey of the uses of tertiary phosphine ligands in a variety of catalytic organic reactions, with 231 references, is presented. In addition to separate discussions on several specific phosphine ligand catalyzed reactions, a brief overview of phosphine ligand design along with basic methods for their preparation and some physical properties are also discussed. Where possible, the relative advantages of alkyl and aryl phosphines in these often industrially important organic reactions are compared.
- 
            1 Introduction 
- 
            2 Ligand Design 
- 
            3 Ligand Preparation 
- 
            3.1 Building Blocks 
- 
            3.2 Methods for Ligand Preparation 
- 
            4 Tertiary Phosphine Applications in Catalysis 
- 
            4.1 Hydroformylations and Hydrogenations 
- 
            4.2 Palladium Catalyzed Arylation Reactions 
- 
            4.3 Palladium Catalyzed Additions to Allylic Systems 
- 
            4.4 Reppe Carbonylations 
- 
            4.5 Ruthenium Catalysts for Metathesis Polymerization 
- 
            5 Conclusions 
Key words
catalysis - hydroformylations - Heck reaction - ligands - carbonylations
- 1 
             
            Frohning CD.Kohlpaintner CW. In Applied Homogeneous Catalysis with Organometallic CompoundsCornils B.Herrmann WA. VCH Publishers; New York: 1996. p.74-75Reference Ris Wihthout Link
- 2 The intensity of academic R&D in catalytic organic reactions discussed here can be
            judged from references we cite. As for industrial effort in 2001 more than 100 patent
            publications disclosed studies directed towards the improvement of catalytic reactions
            potentially useful in pharmaceutical and fine chemical syntheses
            
            Reference Ris Wihthout Link
- 3 
             
            Brandt P.Andersson PG. Synlett 2000, 1092
- 4 
             
            Kamer PCJ.Reek JNH.van Leeuwen PWNM. CHEMTECH 1998, 28(9): 27
- 5 
             
            Trost BM.Van Vranken DL. Chem. Rev. 1996, 96: 395Reference Ris Wihthout Link
- 6 
             
            Kagan HB.Dang T.-P. J. Am. Chem. Soc. 1972, 94: 6429Reference Ris Wihthout Link
- 7a 
             
            Kagan HB. In Asymmetric Synthesis Vol. 5:Morrison JD. Academic Press; Orlando: 1985. Chap. 1.Reference Ris Wihthout Link
- 7b  In  Comprehensive Asymmetric Catalysis  
             
            Jacobsen EN.Pfaltz A.Yamamoto H. Springer; Berlin: 1999.Reference Ris Wihthout Link
- 8a 
             
            Whitesell JK. Chem. Rev. 1989, 89: 1581
- 8b 
             
            Trost Van Vranken DL. Angew. Chem., Int. Ed. Engl. 1992, 31: 228
- 9a 
             
            Inoguchi K.Sakuraba S.Achiwa K. Synlett 1992, 169
- 9b 
             
            Morimoto T.Chiba M.Achiwa K. Chem. Pharm. Bull. 1993, 41: 1149
- 9c 
             
            RajanBabu TV.Casalnuovo AL. J. Am. Chem. Soc. 1996, 118: 6325
- 9d 
             
            Carmichael D.Doucet H.Brown JM. Chem. Commun. 1999, 261
- 9e 
             
            Sannicolo F.Benincori T.Rizzo S.Gladiali S.Pulacchini S.Zotti G. Synthesis 2001, 2327
- 10 
             
            Braunstein P.Naud F. Angew. Chem. Int. Ed. 2001, 40: 680
- 11 
             
            Helmchen G.Pfaltz A. Acc. Chem. Res. 2000, 33: 336
- 12 
             
            Deerenberg S.Pàmies O.Diéguez M.Claver C.Kamer PCJ.van Leeuwen PWNM. J. Org. Chem. 2001, 66: 7626
- 13 
             
            Pàmies O.van Strijdonck GPF.Diéguez M.Deerenberg S.Net G.Ruiz A.Claver C.Kamer PCJ.van Leeuwen PWNM. J. Org. Chem. 2001, 66: 8867
- 14 
             
            Gilbertson SR.Xie D.Fu Z. J. Org. Chem. 2001, 66: 7240
- 15 
             
            Benincori T.Gladiali S.Rizzo S.Sannicolò F. J. Org. Chem. 2001, 66: 5940
- 16 
             
            Sugama H.Saito H.Danjo H.Imamoto T. Synthesis 2001, 2348
- 17 
             
            Fache F.Schulz E.Tommasino ML.Lemaire M. Chem. Rev. 2000, 100: 2159
- 18a 
             
            Oosterom GE.Reek JNH.Kamer PCJ.van Leeuwen PWNM. Angew. Chem. Int. Ed. 2001, 40: 1828
- 18b 
             
            Astruc D.Chardac F. Chem. Rev. 2001, 101: 2991
- 19 
             
            Tsiavaliaris G.Haubrich S.Merckle C.Blümel J. Synlett 2001, 391
- 20 
             
            Allgeier AM.Mirkin CA. Angew. Chem. Int. Ed. 1998, 37: 894
- 21 
             
            Katti KV.Gali H.Smith CJ.Berning DE. Acc. Chem. Res. 1999, 32: 9
- 22a 
             
            Lynn DM.Grubbas RH. J. Am. Chem. Soc. 2001, 123: 3187
- 22b 
             
            Shaughnessy KH.Booth RS. Org. Lett. 2001, 3: 2757
- 23 
             
            De Lue N. Chem. Innovation 2001, 30(11): 33
- Combinatorial methods to find superior ligands may be attractive when rapid methods exist to evaluate catalyst performance in systems of interest.
- 24a 
             
            Reetz MT. Angew. Chem. Int. Ed. 2001, 40: 284
- 24b 
             
            Reetz MT.Becker MH.Klein H.-W.Stockigt D. Angew. Chem. Int. Ed. 1998, 38: 1758
- 24c 
             
            Dahmen S.Brase S. Synthesis 2001, 1431
- 24d 
             
            Jandeleit B.Schaefer DJ.Powers TS.Turner HW.Weinberg WH. Angew. Chem. Int. Ed. 1999, 38: 2492
- 25 
             
            Elsner GM.Regitz E. Houben-Weyl, Methoden der organischen Chemie, Organische Phosphor-Verbindungen Band E1: Thieme Verlag; Stuttgart: 1982. Chap. 3. p.106-183Reference Ris Wihthout Link
- 26 
             Organic Phosphorus Compounds  
             
            Maier L.Kosalopoff GM. Wiley; New York: 1972. Chap. 1. p.1-287Reference Ris Wihthout Link
- 27 
             
            Svara J.Weferling N. In Ullman Encyclopedia of Chemical Technology 5th Ed., Vol. A19:Elvers B.Hawkins S.Schulz G. VCH; Weinheim: 1991. p.545-572Reference Ris Wihthout Link
- 28a 
             
            Pietrusiewicz KM.Zablocka M. Chem. Rev. 1994, 94: 1375
- 28b 
             
            Imamoto TE. Handbook of Organophosphorus ChemistryEngel R. Marcel Dekker; New York: 1992. Chap. 1.
- 28c 
             
            Kagan HB.Sasaki MF. Chemistry of Organophosphorus Compounds Vol. 1:Hartley R. Wiley & Sons; New York: 1990. Chap. 3.
- 28d 
             
            Valentine D. Asymmetric Synthesis Vol. 4:Morrison JD.Scott JW. Academic Press; New York: 1984. p.263-312
- 29 
             
            Rickelton WA. Kirk-Othmer Encyclopedia of Chemical Technology Vol. 18:Kroschwitz J. J. Wiley-Interscience; New York: 1996. p.656-667Reference Ris Wihthout Link
- 30 
             
            Robertson A.Bradaric C.Frampton CS.Mc Nulty J.Capretta A. Tetrahedron Lett. 2001, 42: 2609
- 31a  
            Brown HC. inventors; U.S. 2,584,112.
- 31b 
             
            Hoff MC.Hill P. J. Org. Chem. 1959, 24: 356
- 32a  
            Valentine D. inventors; U.S. 4,857,655.Reference Ris Wihthout Link
- 32b  
            Valentine D. inventors; American Cyanamid, U.S. 5,003,093.Reference Ris Wihthout Link
- 33  
            Calbick CJ,Kuck MJ, andValentine D. inventors; American Cyanamid, U.S. 5,260,485.Reference Ris Wihthout Link
- 34a  
            Calbick CJ,Kuck MA, andValentine D. inventors; American Cyanamid, U.S. 5,174,149.Reference Ris Wihthout Link
- 34b  
            Calbick CJ,Kuck MA, andValentine D. inventors; Cytec Technology Corp., U.S. 5,415,129.Reference Ris Wihthout Link
- 35a  
            Sugiya M,Watanabe T, andSano N. inventors; Nippon Chemical Industry, U.S. 5,892,120.Reference Ris Wihthout Link
- 35b  
            Sugiya M,Watanabe T, andSano N. inventors; Nippon Chemical Industry, U.S. 6,025,525.Reference Ris Wihthout Link
- 36  
            Sugiya M,Watanabe T, andTakeuchi K. inventors; Nippon Chemical Industries, U.S. 5,872,279.Reference Ris Wihthout Link
- 38 
             
            Melvin LS. Tetrahedron Lett. 1981, 22: 3375
- 39a 
             
            Dhawan B.Redmore D. J. Org. Chem. 1984, 49: 4018
- 39b 
             
            Dhawan B.Redmore D. J. Org. Chem. 1986, 51: 179
- 39c 
             
            Dhawan B.Redmore D. Phosphorus, Sulfur Silicon Relat. Elem. 1989, 42: 177
- 40a 
             
            Heinicke J.Böhle I.Tzschach A. J. Organomet. Chem. 1986, 317: 11
- 40b 
             
            Heinicke J.Kadyrov R.Kellner K.Nietzschmann E.Tzschach A. Phosphorus, Sulfur Silicon Relat. Elem. 1989, 44: 209
- 41a 
             
            Paladino J.Guyard C.Thurieau C.Fauchère JL. Helv. Chim. Acta 1993, 76: 2465
- 41b 
             
            Onys’ko PP.Suvalova EA.Chudakova TT.Sinitsa AD. Heteroat. Chem. 1993, 4: 361
- 41c 
             
            Onys’ko PP.Suvalova EA.Chudakova TI.Sinitsa AD. Russ. J. Gen. Chem. 1994, 64: 554
- 42a 
             
            Masson S.Saint-Clair J.-F.Saquet M. Tetrahedron Lett. 1994, 35: 3083
- 42b 
             
            Masson S.Saint-Clair J.-F.Dore A.Saquet M. Bull. Chim. Soc. Fr. 1996, 133: 951
- 43a 
             
            Jardine AM.Vather SM.Modro TA. J. Org. Chem. 1988, 53: 3983
- 43b 
             
            He Z.Modro TA. Synthesis 2000, 565
- 44a 
             
            Demay S.Volant F.Knochel P. Angew. Chem. Int. Ed. 2001, 1235
- 44b 
             
            Demay S.Harms K.Knochel P. Tetrahedron Lett. 1999, 4981
- 45 
             
            Ohff M.Holz J.Quirmbach M.Börner A. Synthesis 1998, 1391
- 46a 
             
            Nakajima M.Miyoshi I.Kanayama K.Hashimoto S.-I.Noji M.Koga K. J. Org. Chem. 1999, 64: 2264
- 46b 
             
            Li X.Yang J.Kozlowski MC. Org. Lett. 2001, 3: 1137
- 47 
             
            Cai D.Payack JF.Bender DR.Hughes DL.Verhoeven TR.Reider PJ. J. Org. Chem. 1994, 59: 7180
- 48 
             
            Ager DJ.East MB.Eisenstadt A.Laneman SA. Chem. Commun. 1997, 2359
- 49 
             
            Kumobayashi H.Miura T.Sayo N.Saito T.Zhang X. Synlett 2001, 1055 ; and references therein
- 50a 
             
            Takaya H.Mashima K.Koyano K.Yagi M.Kumobayashi H.Taketomi T.Akutagawa S.Noyori R. J. Org. Chem. 1986, 51: 629
- 50b 
             
            Miyashita A.Takaya H.Souchi T.Noyori R. Tetrahedron 1984, 40: 1245
- 51 
             
            Grushin VV. J. Am. Chem. Soc. 1999, 121: 5831 ; and references therein
- 52 
             
            Shimada T.Kurushima H.Cho Y.-H.Hayashi T. J. Org. Chem. 2001, 66: 8854
- 53 
             
            Hayashi T.Hirate S.Kitayama K.Tsuji H.Torii A.Uozumi Y. J. Org. Chem. 2001, 66: 1441
- 54 
             
            Hayashi T. Acc. Chem. Res. 2000, 33: 354
- 55 
             
            Yin J.Buchwald SL. J. Am. Chem. Soc. 2000, 122: 12051
- 56 
             
            Ito K.Kashiwagi R.Iwasaki K.Katsuki T. Synlett 1999, 1563
- 57  
            Hillhouse JH. inventors; Cytec Technology Corp., U.S. 5,550,295.Reference Ris Wihthout Link
- 58 
             
            Stark GA.Riermeier TH.Beller M. Synth. Commun. 2000, 30: 1703
- 59 
             
            Shelby Q.Kataoka N.Mann G.Hartwig J. J. Am. Chem. Soc. 2000, 122: 10718Reference Ris Wihthout Link
- 60 
             
            Han L.-B.Tanaka M. Chem. Commun. 1999, 395 ; and references therein
- 61 
             
            Kazankova MA.Efimova IV.Kochetkov AN.Afanas’ev VV.Beletskaya IP.Dixneuf PH. Synlett 2001, 497
- 62 
             
            Han L.-B.Zhao C.-Q.Tanaka M. J. Org. Chem. 2001, 66: 5929Reference Ris Wihthout Link
- 63 
             
            Zhao C.-Q.Han L.-B.Goto M.Tanaka M. Angew. Chem. Int. Ed. 2001, 40: 1929Reference Ris Wihthout Link
- 64a 
             
            Han L.-B.Hua R.Tanaka M. Angew. Chem. Int. Ed. 1998, 37: 94Reference Ris Wihthout Link
- 64b 
             
            Han L.-B.Tanaka M. J. Am. Chem. Soc. 1996, 118: 1571Reference Ris Wihthout Link
- 65a 
             
            Tomori H.Fox JM.Buchwald SL. J. Org. Chem. 2000, 65: 5334
- 65b 
             
            Frid M.Pérez D.Peat AJ.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 9469
- 66 
             
            Tsuruta H.Imamoto T. Synthesis 2001, 999
- 67 
             
            Langer F.Puntener K.Sturmer R.Knochel P. Tetrahedron: Asymmetry 1997, 8: 715
- 68 
             
            Greenfield SJ.Gilbertson SR. Synthesis 2001, 2337
- 69a 
             
            Gilbertson SR.Wang X. J. Org. Chem. 1996, 61: 434
- 69b 
             
            Gilbertson SR.Chen G.McLoughlin M. J. Am. Chem. Soc. 1994, 116: 4481
- 69c 
             
            Porte AM.Reibenspies J.Burgess K. J. Am. Chem. Soc. 1998, 120: 9180
- 70 
             
            Edwards PG.Newman PD.Abdul Malik KM. Angew. Chem. Int. Ed. 2000, 39: 2922
- 71a 
             
            Edwards PG.Whatton ML.Haigh R. Organometallics 2000, 19: 2652
- 71b 
             
            Edwards PG.Newman PD.Hibbs DE. Angew. Chem. Int. Ed. 2000, 39: 2722
- 72 
             
            Lambert B.Desreux JF. Synthesis 2000, 1668
- 73a 
             
            Herrmann WA.Brossmer C.Öfele K.Reisinger C.-P.Priermeier T.Beller M.Fischer H. Angew. Chem., Int. Ed. Engl. 1995, 34: 1844
- 73b 
             
            Brunel JM.Heumann A.Buono G. Angew. Chem. Int. Ed. 2000, 39: 1946
- 73c 
             
            Louie J.Hartwig JF. Angew. Chem., Int. Ed. Engl. 1996, 35: 2359
- 74 
             
            Ohff M.Ohff A.van der Boom ME.Milstein D. J. Am. Chem. Soc. 1997, 119: 11687
- 75 
             
            Yin J.Rainka MP.Zhang X.-X.Buchwald SL. J. Am. Chem. Soc. 2002, 104: 1162
- 76a 
             
            Vyskocil S.Smircina M.Hanu V.Poláek M.Kocovsk P. J. Org. Chem. 1998, 63: 7738
- 76b 
             
            Kocovsk P.Vyskocil S.Císarova I.Sejbal J.Tilerova I.Smrcina M.Lloyd-Jones GC.Stephen SC.Butts CP.Murray M.Langer V. J. Am. Chem. Soc. 1999, 121: 7714
- 77 
             
            Stinson SC. Chem. Eng. News 2001, 78(43): 23
- 78a 
             
            Burk MJ.Feaster JE.Nugent WA.Harlow RL. J. Am. Chem. Soc. 1993, 115: 10125
- 78b 
             
            Burk MJ.Feaster JE.Harlow RL. Organometallics 1990, 9: 2653
- 79 
             
            Burk MJ. Acc. Chem. Res. 2000, 33: 363
- 80a 
             
            Jiang Q.Xiao D.Zhang Z.Cao P.Zhang X. Angew. Chem. Int. Ed. 1999, 38: 516
- 80b 
             
            Hamada Y.Seto N.Ohmori H.Hatano K. Tetrahedron Lett. 1996, 37: 7565
- 80c  
            Berens U. inventors; Chirotech Technology Ltd. U.S. 5,936,109.
- 80d 
             
            Holz J.Quirmbach M.Schmidt U.Heller D.Stürmer R.Börner A. J. Org. Chem. 1998, 63: 8031
- 80e 
             
            Brunel JM.Legrand O.Reymond S.Buono G. J. Am. Chem. Soc. 1999, 121: 5807
- 80f 
             
            Marinetti A.Jus S.Labrue F.Lemarchand A.Genêt J.-P.Ricard L. Synthesis 2001, 2095
- 80g 
             
            Vedejs E.Daugulis O. J. Am. Chem. Soc. 1999, 121: 5813
- 80h 
             
            Landis CR.Jin W.Owen JS.Clark TP. Angew. Chem. Int. Ed. 2001, 40: 3432
- 80i 
             
            Constantieux T.Brunel J.-M.Labande A.Buono G. Synlett 1998, 49
- 80j 
             
            Berens U.Burk MJ.Gerlach A.Hems W. Angew. Chem. Int. Ed. 2000, 39: 1981
- 80k 
             
            Brenchley G.Fedouloff M.Merifield E.Wills M. Tetrahedron: Asymmetry 1996, 7: 2809
- 80l 
             
            Breeden S.Cole-Hamilton DJ.Foster DF.Schwarz GJ.Wills M. Angew. Chem. Int. Ed. 2000, 39: 4106
- 80m 
             
            Stranne R.Vasse JL.Moburg C. Org. Lett. 2001, 3: 2525
- 80n 
             
            Reetz MT.Waldvogel SR.Goddard R. Heterocycles 2000, 52: 935
- 80o 
             
            Baccolini G.Boga C.Buscaroli RA. Synthesis 2001, 1938
- 80p 
             
            Fujie N.Matsui M.Achiwa K. Chem. Pharm. Bull. 1999, 47: 436
- 81 
             
            Fries G.Wolf J.Pfeiffer M.Stalke D.Werner H. Angew. Chem. Int. Ed. 2000, 39: 564
- 82 
             
            Schumann M.Trevitt M.Redd A.Gouverneur V. Angew. Chem. Int. Ed. 2000, 39: 2491
- 83 
             
            Knowles WS.Sabacky MJ.Vineyard BD. J. Am. Chem. Soc. 1995, 97: 2567
- 84 
             
            Zon G.Mislow K. Fortschr. Chem. Forsch. 1971, 19: 61
- 85a 
             
            Juge S.Stephan M.Merdes R.Genet JP.Halut-Desportes S. J. Chem. Soc., Chem. Commun. 1993, 531
- 85b 
             
            Juge S.Stephan M.Lafitte JA.Genet JP. Tetrahedron Lett. 1990, 31: 6357
- 85c 
             
            Juge S.Genet JP. Tetrahedron Lett. 1989, 30: 2783
- 86 
             
            Corey EJ.Chen Z.Tanoury GJ. J. Am. Chem. Soc. 1993, 115: 11000
- 87 
             
            Vedejs E.Donde Y. J. Am. Chem. Soc. 1997, 119: 9293
- 88 
             
            Muci AR.Campos KR.Evans DA. J. Am. Chem. Soc. 1995, 117: 9075
- 89 
             
            Beak P.Anderson DR.Curtis MD.Laumer JM.Pippel DJ.Weisenburger GA. Acc. Chem. Res. 2000, 33: 715
- 90 
             
            Yamanoi Y.Imamoto T. J. Org. Chem. 1999, 64: 2988
- 91a 
             
            Imamoto T.Watanabe J.Wada Y.Masuda H.Yamada H.Tsuruta H.Matsukawa S.Yamaguchi Y. J. Am. Chem. Soc. 1998, 120: 1635
- 91b 
             
            Ohashi A.Imamoto T. Org. Lett. 2001, 3: 373
- 92a 
             
            Wolfe B.Livinghouse T. J. Am. Chem. Soc. 1998, 120: 5116
- 92b 
             
            Wolfe B.Livinghouse T. J. Org. Chem. 2001, 66: 1514
- 93 
             
            Heath H.Wolfe B.Livinghouse T.Bae SK. Synthesis 2001, 2341
- 94a 
             
            Imamoto T.Matsuo M.Nonomura T.Kishikawa K.Yanagawa M. Heteroat. Chem. 1993, 4: 475
- 94b 
             
            Imamoto T.Oshiki T.Onozawa T.Matsuo M.Hikosaka T.Yanagawa M. Heteroat. Chem. 1992, 3: 563
- 95a 
             
            Graf C.-D.Malan C.Knochel P. Angew. Chem. Int. Ed. 1998, 37: 3014
- 95b 
             
            Graf C.-D.Malan C.Harms K.Knochel P. J. Org. Chem. 1999, 64: 5581
- 96 
             
            Mislow K.Siegel J. J. Am. Chem. Soc. 1984, 106: 3319
- 97 
             
            Bei X.Turner HW.Weinberg WH.Guram AS.Petersen JL. J. Org. Chem. 1999, 64: 6797
- 98 
             
            Ohmura T.Yamamoto Y.Miyaura N. J. Am. Chem. Soc. 2000, 122: 4990
- Utility of tri-t-butylphosphine in Pd catalyzed ArX chemistry. Consult individual references for form of Pd complex used, solvent, and additives all of which may affect catalyst performance significantly.
- 99a Heck reaction:  
            Littke AF.Fu GC. J. Org. Chem. 1999, 64: 10
- 99b Heck reaction:  
            Littke AF.Fu G. J. Am. Chem. Soc. 2001, 123: 6989
- 99c Heck reaction:  
            Shaughnessy KH.Kim P.Hartwig JF. J. Am. Chem. Soc. 1999, 121: 2123
- 99d Suzuki reaction:  
            Littke AF.Dai C.Fu GC. J. Am. Chem. Soc. 2000, 122: 4020
- 99e Suzuki reaction:  
            Littke AF.Fu GC. Angew. Chem. Int. Ed. 1998, 37: 3387
- 99f  
            Monteith M. inventors; WO 98 16486. Suzuki reaction: ; Chem. Abstr. 1998, 128, 294592,
- 99g  Suzuki reaction:  
            Cornils B. Proc. Res. Dev. 1998, 2: 121
- 99h Suzuki reaction:   
            Littke AF.Fu GC. Angew. Chem. Int. Ed. 1999, 38: 2411
- 99i Sonagashira reaction:  
            Hundertmark T.Littke AF.Buchwald SL.Fu GC. Org. Lett. 2000, 2: 1729
- 99j Diaryl ether formation:  
            Mann G.Incarvito C.Rheingold AL.Hartwig JF. J. Am. Chem. Soc. 1999, 121: 3224
- 99k Amination:  
            Hartwig JF. Polym. Preprints (Am. Chem Soc., Div Polym. Chem.) 2000, 41: 420
- 99l Amination:  
            Hartwig JF.Goodson FE.Louie J.Hauck S. Polym. Mater. Sci. Eng. 1999, 80: 41
- 99m  
            Lin SL,Zhou W, andMatcham GW. inventors; Celgro US 6,107,521. Amination: 2000; Chem. Abstr. 2000, 133, 179296
- 99n Amination:  
            Nishiyama M.Yamamoto T.Koie Y. Tetrahedron Lett. 1998, 39: 617
- 99o Amination:  
            Yamamoto T.Nishiyama M.Koie Y. Tetrahedron Lett. 1998, 39: 2367
- 99p Amination:  
            Yamamoto T.Nishiyama M.Koie Y. Toso Kenkyu Hokoku 1997, 41: 49 ; Chem. Abstr. 1998, 128, 180180
- 99q Amination:  
            Hartwig JF.Kawatsura M.Hauck SI.Shaughnessy KH.Alcazar-Roman LM. J. Org. Chem. 1999, 64: 5575
- 99r Amination:  
            Watanabe M.Yamamoto T.Nishiyama M. Angew. Chem. Int. Ed. 2000, 39: 2501
- 99s Amination:  
            Goodson FE.Hauck SI.Hartwig JF. J. Am. Chem. Soc. 1999, 121: 7527
- 99t Amination:  
            Braig T.Muller DC.Gross M.Meerholz K.Nuyken O. Macromol. Rapid Commun. 2000, 21: 583
- 99u Negishi cross coupling:  
            Dai C.Fu GC. J. Am. Chem. Soc. 2001, 123: 2719
- 99v Arylation of ketones malonates etc.:  
            Kawatsura M.Hartwig JF. J. Am. Chem. Soc. 1999, 121: 1473
- 99w  
            Hartwig JF,Kawatsura M, andHauck SI. inventors; U.S. 6,100,398. Arylation of ketones malonates etc.: ; Chem. Abstr. 2000, 131, 310548
- 99x Heterocyclic substitution:  
            Ogawa K.Radke KR.Rothstein SD.Rasmussen SC. J. Org. Chem. 2000, 66: 9067
- 100a 
             
            Goerlich JR.Schmutzler R. Phosphorus, Sulfur Silicon Relat. Elem. 1995, 102: 211
- 100b 
             
            Stauffer SR.Beare NA.Stambuli JP.Hartwig JF. J. Am. Chem. Soc. 2001, 123: 4641
- 100c 
             
            Beare NA.Hartwig JF. J. Org. Chem. 2002, 67: 541
- 101a 
             
            Ehrentraut A.Zapf A.Beller M. Synlett 2000, 1589
- 101b 
             
            Zapf A.Ehrentraut A.Beller M. Angew. Chem. Int. Ed. 2000, 39: 4153
- 101c 
             
            Stambuli JP.Kuwano R.Hartwig JF. Angew. Chem. Int. Ed. 2002, 41: 4746
- 102 
             
            Simal F.Demonceau A.Noels AF. Angew. Chem. Int. Ed. 1999, 38: 538
- 103 
             
            Wolfe JP.Singer RA.Yang BH.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 9550
- 104 
             
            Aranyos A.Old DW.Kiyomori A.Wolfe JP.Sadighi JP.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 4369
- 105 
             
            Old DW.Wolfe JB.Buchwald SL. J. Am. Chem. Soc. 1998, 120: 9722
- 106 
             
            Karsch HH. Z. Naturforsch. B: Chem. Sci. 1983, 38: 1027
- 107 
             
            Hansen SM.Volland MAO.Rominger F.Eisenträger F.Hofmann P. Angew. Chem. Int. Ed. 1999, 38: 1273
- 108 
             
            Ohashi A.Imamoto T. Org. Lett. 2001, 3: 373
- 109a 
             
            Ben-David Y.Portnoy M.Milstein D. J. Am. Chem. Soc. 1989, 11: 8742
- 109b 
             
            Ben-David Y.Portnoy M.Milstein D. J. Chem. Soc., Chem. Commun. 1989, 1816
- 109c 
             
            Portnoy M.Milstein D. Organometallics 1993, 12: 1655
- 109d 
             
            Ben-David Y.Gozin M.Portnoy M.Milstein D. J. Mol. Catal. 1992, 73: 173
- 109e 
             
            Blum J.Berlin O.Milstein D.Ben-David Y.Wassermann BC.Schutte S.Schumann H. Organometallics 2000, 571
- 110 
             
            Kawatsura M.Hartwig JF. Organometallics 2002, 20: 1960
- 111 
             
            Shan Z.Xiong Y.Zhao D. Tetrahedron 1999, 55: 3893
- 112a 
             
            Nakajima M.Miyoshi I.Kanayama K.Hashimoto SI.Noji M.Koga K. J. Org. Chem. 1999, 64: 2264
- 112b 
             
            Li X.Yang J.Koslowski MC. Org. Lett. 2001, 3: 1137
- 113 
             
            Becker JJ.Gagne MR. J. Am. Chem. Soc. 2001, 123: 9476
- 114 
             
            Reetz MT.Mehler G. Angew. Chem. Int. Ed. 2000, 39: 3889
- 115 
             
            Reetz MT.Sell T. Tetrahedron Lett. 2000, 41: 6333
- 116 
             
            Naasz R.Arnold LA.Pineschi M.Keller E.Feringa BL. J. Am. Chem. Soc. 1999, 121: 1104
- 117 
             
            Ishihara K.Kobayashi J.Inanaga K.Yamamoto H. Synlett 2001, 394
- 118 
             
            Yamada YMA.Shibasaki M. Tetrahedron Lett. 1998, 39: 5561
- 119a 
             
            Singer RA.Buchwald SL. Tetrahedron Lett. 1999, 1095
- 119b 
             
            Vyskocil M.Smrcina M.Kocovsky P. Tetrahedron Lett. 1998, 39: 9289
- 120 
             
            Vyskocil S.Jaracz S.Smrcina M.ticha M.Hanu V.Polàek M.Kocovsky P. J. Org. Chem. 1998, 63: 7727
- 121 
             
            Rossini C.Fanzini L.Raffaelli A.Salvadori P. Synthesis 1992, 503
- 122 
             
            Miyano S.Nawa M.Mori A.Hashimoto H. Bull. Chem. Soc. Jpn. 1984, 57: 2171
- 123 
             
            Reetz MT.Haderlein G.Angermund K. J. Am. Chem. Soc. 2000, 122: 996
- 124 
             
            Ohkuma T.Doucet H.Pham T.Mikami K.Korenaga T.Terada M.Noyori R. J. Am. Chem. Soc. 1998, 120: 1086
- 125 
             
            Shaughnessy KH.Hamann BC.Hartwig JF. J. Org. Chem. 1998, 63: 6546
- 126 
             
            Wolfe JP.Buchwald SL. J. Org. Chem. 2000, 65: 1144
- 127 For example see:  
            Takaya H.Ohta T.Noyori R. In Catalytic Asymmetric SynthesisOjima I. VCH; New York: 1993. p.1-39Reference Ris Wihthout Link
- 128 
             
            Farraris D.Young B.Dudding WJ.Drury WJ.Lectka T. Tetrahedron 1999, 55: 8869
- 129 
             
            Zhang X.Mashima K.Koyano K.Sayo N.Kumobayashi H.Akutagawa S.Takaya S. J. Chem. Soc., Perkin Trans. 1 1994, 2309
- 130a 
             
            Uozumi Y.Hayashi T. J. Am. Chem. Soc. 1991, 113: 9987
- 130b 
             
            Hayashi T. Acta Chem. Scand. 1996, 50: 259
- 131a 
             
            Torraca KE.Kuwabe S.-I.Buchwald SL. J. Am. Chem. Soc. 2000, 122: 12907
- 131b 
             
            Torraca KE.Huang X.Parrish CA.Buchwald SL. J. Am. Chem. Soc. 2001, 123: 10770
- See ref. 76 also:
- 132a 
             
            Ding K.Wang Y.Yun H.Liu J.Wu Y.Terada M.Ohkubo Y.Mikami K. Chem.-Eur. J. 1999, 5: 1734
- 132b 
             
            Sumi K.Ikariya T.Noyori R. Can. J. Chem. 2000, 78: 697
- 133 
             
            Chieffi A.Kamikawa K.Åhman J.Fox JM.Buchwald SL. Org. Lett. 2001, 3: 1897
- 134 
             
            Hamada T.Chieffi A.Åhman J.Buchwald SL. J. Am. Chem. Soc. 2002, 124: 1261
- 135 
             
            Reetz MT.Gosberg A.Goddard R.Kyang SH. Chem. Commun. 1998, 2077
- 136 
             
            Hamann B.Hartwig J. J. Am. Chem. Soc. 1998, 120: 7369
- 137a 
             
            Butler IR.Cullen WR.Mann BE.Nurse CR. J. Organomet. Chem. 1985, 280: C47
- 137b  
            Sielcken OE. inventors; DSM and duPont, EP 0,662,467.
- 137c 
             
            Kiss G. Chem. Rev. 2001, 101: 3435
- 137d 
             
            Burk MJ.Harper GP.Lee JR.Kalberg C. Tetrahedron Lett. 1994, 35: 4963
- 137e 
             
            Cullen WR.Kim TJ.Einstein FWB. Organometallics 1983, 2: 714
- 137f 
             
            Butler IR.Cullen WR.Kim TJ.Rettig SJ. Organometallics 1985, 4: 972
- 138 
             
            Lautens M.Fagnou K.Rovis T. J. Am. Chem. Soc. 2000, 122: 5650
- 139a 
             
            Feuerstein M.Laurenti D.Doucet H.Santelli M. Synthesis 2001, 2320
- 139b 
             
            Feuerstein M.Doucet H.Santelli M. J. Org. Chem. 2001, 66: 5923
- 139c 
             
            Feuerstein M.Doucet H.Santelli M. Synlett 2001, 1458
- 139d 
             
            Laurenti D.Feuerstein M.Pépe G.Doucet H.Santelli M. J. Org. Chem. 2001, 66: 1633
- 140 
             
            Tolman CA. Chem. Rev. 1977, 77: 313Reference Ris Wihthout Link
- 141 
             
            McAuliffe CA. In Comphrehensive Coordination Chemistry Vol. 6:Wilkinson G.Gillard RD.McCleverty JA. Pergamon; New York: 1987. p.989-1066Reference Ris Wihthout Link
- 142 
             
            Mosbo JA.DeSanto JT.Storhoff BN.Bock PL.Bloss RE. Inorg. Chem. 1980, 19: 3086
- 143 
             
            Basato M. J. Chem. Soc., Dalton Trans. 1986, 217
- 144 
             
            Fernandez AI.Lee TY.Reyes C.Prock A.Giering WP.Haar CM.Nolan SP. J. Chem. Soc., Perkin Trans. 2 1999, 2631
- 145 
             
            Maier L. In Organic Phosphorus Compounds Vol. 1:Kosolapoff G.Maier L. John Wiley and Sons Inc.; New York: 1972. p.1-287Reference Ris Wihthout Link
- 146 
             
            Bush RC.Angelici RJ. Inorg. Chem. 1988, 27: 681
- 147 
             
            Slaugh LH.Mullineaux RD. J. Organomet. Chem. 1968, 13: 469
- 148 
             
            Böhm LL. In Applied Homogeneous Catalysis with Organometallic CompoundsCornils B.Herrmann WA. VCH Publishers; New York: 1996. p.251-256Reference Ris Wihthout Link
- 149a  
            Arhancet JP, andSlaugh LH. inventors; Shell Oil Company, U.S. 5,304,686.Reference Ris Wihthout Link
- 149b  
            Arhancet JP, andSlaugh LH. inventors; Shell Oil Company, U.S. 5,304,691.Reference Ris Wihthout Link
- 150a 
             
            MacDougall JK.Simpson MC.Green MJ.Cole-Hamilton DJ. J. Chem. Soc., Dalton Trans. 1996, 1161
- 150b 
             
            Reetz MT.Waldvogel SR.Goddard R. Heterocycles 2000, 58: 935
- 151 
             
            Fukuoka A.Kosugi W.Morishita F.Hirano M.McCaffrey L.Henderson W.Komiya S. Chem. Commun. 1999, 489
- 152a 
             
            Beletskaya IP.Cheprakov AV. Chem. Rev. 2000, 100: 3009
- 152b 
             
            de Meijere A.Meyer FE. Angew. Chem., Int. Ed. Engl. 1994, 33: 2379
- 152c Intramolecular reactions cf.:  
            Link JT.Overman LE. CHEMTECH 1998, 28(8): 19
- 152d Anionic Pd(0) and Pd(II) intermediates:  
            Amatore C.Jutand A. Acc. Chem. Res. 2000, 33: 314
- 152e 
             
            Beller M.Riermeier TH.Stark G. Transition Metal Organic Synthesis Vol. 1:Beller M.Bolm C. Wiley-VCH Verlag GmbH; Weinheim Germany: 1998. p.208
- 152f 
             
            Cabri W.Candiani I. Acc. Chem. Res. 1995, 28: 2
- 152g 
             
            Heck RF. Org. React. 1982, 27: 345
- 153a 
             
            Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457
- 153b 
             
            Suzuki A. Pure Appl. Chem. 1994, 66: 213
- 153c 
             
            Suzuki A. J. Organomet. Chem. 1999, 576: 147
- 153d 
             
            Buchwald SL.Fox JM. Strem Chemiker 2000, XVIII: 1
- 154a 
             
            Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508Reference Ris Wihthout Link
- 154b A comprehensive listing of Stille reactions reported 1983-1995:  
            Farina V.Krishnamurthy V. The Stille Reaction Wiley; New York: 1998.Reference Ris Wihthout Link
- 155a 
             
            Hartwig JF. Angew. Chem. Int. Ed. 1998, 37: 2046
- 155b 
             
            Theil F. Angew. Chem. Int. Ed. 1999, 38: 2345
- 155c 
             
            Beller M.Riermeier TH. Transition Metal Organic Synthesis Vol. 1:Beller M.Bolm C. Wiley-VCH GmbH; Weinheim, Germany: 1998. p.184-194
- 155d  
            Ref. [105] and references cited therein 
- 156a 
             
            Bolm C.Hildebrand JP.Muñiz K.Hermanns N. Angew. Chem. Int. Ed. 2001, 40: 3284
- 156b 
             
            Tenaglia A.Heumann A. Angew. Chem. Int. Ed. 1999, 38: 2180
- 156c 
             
            Loiseleur O.Hayashi M.Schmees N.Pfaltz A. Synthesis 1997, 1338
- A Pd/P(i-C4H9)3 complex has been reported useful to form 2-cyano-4′-methylbiphenyl a common intermediate for: Losartan potassium® (duPont), Irbesartan® (Sanofi), Valsartin® (Novartis), and Candesartan® (Takeda).
- 157a See:  
            Stinson SC. Chem. Eng. News 1998, 76(3): 49
- 157b See also:  
            Stinson SC. Chem. Eng. News 1998, 76(28): 57
- 157c  
            Monteith MJ. inventors; Zeneca Ltd. WO 9816848. See also: ; Chem. Abstr. 1998, 128, 294592
- 158 
             
            Lloyd-Williams P.Giralt E. Chem. Soc. Rev. 2001, 30: 145
- 159 For use of a Pd/neomenthyldiphenylphosphine catalyst c.f.;  
            Stinson SC. Chem. Eng. News 1999, 77(3): 74
- 160 
             
            Aslam M.Elango V.Davenport KG. Synthesis 1989, 869
- 161 
             
            Evans DA.DeVries KM. In Glycopeptide Antibiotics Drugs and the Pharmaceutical Sciences Vol. 63:Nagarajan R. Marcel Dekker Inc.; New York: 1994. p.63-104Reference Ris Wihthout Link
- 162a  
            The sp2 C-X bond dissociation energies decrease in the order C-Cl = 402kJmol-1, C-Br = 339kJmol-1,C-I = 272kJmol-1 at 298 Reference Ris Wihthout Link
- 162b 
             
            Grushin VV.Alper H. Chem. Rev. 1994, 94: 1047Reference Ris Wihthout Link
- 163a  
            For the phosphines PPh3-n(c-C6H11)n some reported pKa values are: PPh3, 2.73; PPh2(c-C6H11), 5.05; PPh(c-C6H11)2, 7.38; P(c-C6H11)3, 9.7 
- 163b 
             
            Simal F.Demonceau A.Noels AF. Angew. Chem. Int. Ed. 1999, 38: 538
- 164 
             
            Albisson DA.Bedford RB.Lawrence SE.Scully PN. Chem Commun. 1998, 2095
- 165 
             
            Valentine D.Tilley JW.LeMahieu RA. J. Org. Chem. 1981, 46: 4614
- 166a 
             
            Zhang C.Huang J.Trudell ML.Nolan SP. J. Org. Chem. 1999, 64: 3804
- 166b 
             
            Huang J.Nolan SP. J. Am. Chem. Soc. 1999, 121: 9889
- 166c 
             
            Yang C.Nolan SP. Synlett 2001, 1539
- 166d 
             
            Lee S.Beare NA.Hartwig JF. J. Am. Chem. Soc. 2001, 123: 8410
- 167 
             
            Alcazar-Roman LM.Hartwig JF.Rheingold AL.Liable-Sands LM.Guzei IA. J. Am. Chem. Soc. 2000, 122: 4618
- 168 
             
            Culkin DA.Hartwig JF. J. Am. Chem. Soc. 2001, 123: 5816
- 169 
             
            Roy AH.Hartwig JF. J. Am. Chem. Soc. 2001, 123: 1232
- 170a 
             
            Hartwig JF. Pure Appl. Chem. 1999, 71: 1417
- 170b 
             
            Hartwig JF. Acc. Chem. Res. 1998, 31: 852
- 171a  
            See ref. [24] 
- 171b See also:  
            Porte AM.Reibenspies J.Burgess K. J. Am. Chem. Soc. 1998, 120: 9180
- 171c 
             
            Watkins K. Chem. Eng. News 2001, 79(43): 30
- 172a Arylation of ethyl cyanoacetate:  
            Stambuli JP.Stauffer SR.Shaughnessy KH.Hartwig JF. J. Am. Chem. Soc. 2001, 123: 2677
- 172b  
            High throughput screening of Heck reactions see ref. [101c] 
- 172c Diene hydroamination fluorescence color assay:  
            Loeber O.Kawatsura M.Hartwig JF. J. Am. Chem. Soc. 2001, 123: 4366
- 172d  
            High throughput evaluation for addition of amines to acrylic acid see ref. [113] 
- 172e Capillary array electrophoretic method for fast screening of enantioselective catalysts:
             
            Reetz MT.Kühling KM.Deege A.Hinrichs H.Belder D. Angew. Chem. Int. Ed. 2000, 39: 3891
- 173 
             
            Parrish CA.Buchwald SL. J. Org. Chem. 2001, 66: 3820
- 174  
            Buchwald SL,Plante OJ, andSeeberger PH. inventors; WO 2001038377. ; Chem. Abstr. 2001, 134, 367135Reference Ris Wihthout Link
- 175 
             
            Wolfe JP.Buchwald SL. Angew. Chem Int. Ed. 1999, 38: 2413
- 176 
             
            Zapf A.Beller M. Chem.-Eur. J. 2000, 6: 1830
- 177 
             
            Beller M.Fischer H.Herrmann WA.Öfele K.Brossmer C. Angew. Chem. Int. Ed. 1995, 34: 1848
- 178 
             
            Zim D.Gruber AS.Ebeling G.Dupont J.Monteiro AL. Org. Lett. 2000, 2: 2881
- 179 
             
            Bumagin NA.Bykov VV. Tetrahedron 1997, 53: 14437
- 180 
             
            Ennis DS.McManus J.Wood-Kaczmar W.Richardson J.Smith GE.Carstairs A. Org. Process Res. Dev. 1999, 3: 248
- 181a 
             
            Inada K.Miyaura N. Tetrahedron 2000, 56: 8657
- 181b 
             
            Inada K.Miyaura N. Tetrahedron 2000, 56: 8661
- 182 
             
            Hong R.Hoen R.Zhang J.Lin G.-q. Synlett 2001, 1527
- 184 
             
            Beller M.Zapf A. Synlett 1998, 7: 792
- 185 
             
            Gurtler C.Buchwald SL. Chem.-Eur. J. 1999, 5: 3107
- 186 
             
            Reetz MT.Lohmer G.Schwickardi R. Angew. Chem. Int. Ed. 1998, 37: 481
- Other ligand free Pd and Pd-Ni catalysts for Heck and Suzuki reactions include:
- 187a 
             
            Reetz M.Westermann E. Angew. Chem. Int. Ed. 2000, 39: 165
- 187b 
             
            Reetz MT.Westermann E.Lohmer R.Lohmer G. Tetrahedron Lett. 1998, 8449
- 187c  
            Reetz M,Lohmer G,Lohmer R, andWestermann E. inventors; DE 19843012. ; Chem. Abstr. 2000, 132, 222334
- 187d Pd or Pd-Ni clusters:  
            Reetz MT.Breinbauer R.Wanninger K. Tetrahedron Lett. 1996, 37: 4499
- 188a 
             
            Fox JM.Huang X.Chieffi A.Buchwald SL. J. Am. Chem. Soc. 2000, 122: 1360
- 188b 
             
            Palucki M.Buchwald SL. J. Am. Chem. Soc. 1997, 119: 11108
- 189 
             
            Moradi WA.Buchwald SL. J. Am. Chem. Soc. 2000, 123: 7996
- 190 
             
            Satoh T.Kawamura Y.Miura M.Nomura M. Angew. Chem. Int. Ed. Engl. 1997, 36: 1740
- 191 
             
            Parrish CA.Buchwald SL. J. Org. Chem. 2001, 66: 2498
- 192 
             
            Watanabe M.Nishiyama M.Koie Y. Tetrahedron Lett. 1999, 40: 8837
- 193a 
             
            Yang BH.Buchwald SL. J. Organomet. Chem. 1999, 576: 125
- 193b 
             
            Wolfe JP.Wagaw S.Marcoux J.-F.Buchwald SL. Acc. Chem. Res. 1998, 31: 805
- 194 
             
            Harris MC.Geis O.Buchwald SL. J. Org. Chem. 1999, 64: 6019
- 195 
             
            Harris MC.Buchwald SL. J. Org. Chem. 2000, 65: 5327
- 196 
             
            Wolfe JP.Tomori H.Sadighi JP.Yin J.Buchwald SL. J. Org. Chem. 2000, 65: 1158
- 197 
             
            Ali MH.Buchwald SL. J. Org. Chem. 2001, 66: 2560
- 198 
             
            Lipschutz BH.Ueda H. Angew. Chem. Int. Ed. 2000, 39: 4492
- 199 
             
            Lee S.Hartwig JF. J. Org. Chem. 2001, 66: 3402Reference Ris Wihthout Link
- 200 
             
            Stauffer SR.Lee S.Stambuli JP.Hauck SI.Hartwig JF. Org. Lett. 2000, 2: 1423Reference Ris Wihthout Link
- 201 
             
            Wagaw S.Yang BH.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 10251Reference Ris Wihthout Link
- 202 
             
            Beller M.Breindl C.Riermeier TH.Tillack A. J. Org. Chem. 2001, 66: 1403
- 203 
             
            Watanabe M.Yamamoto T.Nishiyama M. Angew. Chem Int. Ed. 2000, 39: 2501
- 204 
             
            Zhang X.-X.Buchwald SL. J. Org. Chem. 2000, 65: 8027
- 205 
             
            Old DW.Harris MC.Buchwald SL. Org. Lett. 2000, 2: 1403
- 206 
             
            Zhang X.-X.Sadighi JP.Mackewitz TW.Buchwald SL. J. Am. Chem. Soc. 2000, 122: 7606
- 207 
             
            Kawatsura M.Hartwig JF. J. Am. Chem. Soc. 2000, 122: 9546
- 208 
             
            Beller M. In Applied Homogeneous Catalysis with Organometallic CompoundsCornils B.Herrmann WA. VCH; Weinheim: 1996. p.148-159Reference Ris Wihthout Link
- 209 
             
            Trost BM. Acc. Chem. Res. 1980, 13: 385
- 210 Regioselective and enantioselective additions to unsymmetric systems such as 1-monosubstituted
            allyls present additional problems:  
            Trost BM.Toste FD. J. Am. Chem. Soc. 1999, 121: 454
- 211 
             
            Stranne R.Vasse J.-L.Moberg C. Org. Lett. 2001, 3: 2525
- 212a 
             
            Ito K.Kashiwagi R.Iwasaki K.Katsuki T. Synlett 1999, 1563
- 212b 
             
            Ito K.Kashiwagi R.Hayashi S.Uchida T.Katsuki T. Synlett 2001, 2: 284
- For other chiral P,N ligands used in Pd catalysts for asymmetric allylations see:
- 213a 
             
            Constantiuex T.Brunel J.Labande A.Buono G. Synlett 1998, 49
- 213b 
             
            Denmark SE.Wynn T. J. Am. Chem. Soc. 2001, 123: 6199
- 213c 
             
            Achiwa I.Yamazaki A.Achiwa K. Synlett 1998, 45
- 213d 
             
            Gilbertson SR.Genov DG.Rheingold AL. Org. Lett. 2000, 2: 2885
- 214a  
            Suykerbyk JCL,Drent E, andPringle PG. inventors; Shell WO 98/42717.Reference Ris Wihthout Link
- 214b  
            Drent E,Pello DHL, andHassalaar M. inventors; Shell U.S. 5,436,356.Reference Ris Wihthout Link
- 215a 
             
            Buchmeiser MR. Chem. Rev. 2000, 100: 1565
- 215b 
             
            Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012
- 216a 
             
            Schrock RR.Murdzek JS.Bazan GC.Robbins J.Di Mare M.O’Regan M. J. Am. Chem. Soc. 1990, 112: 3875
- 216b 
             
            Oskam JY.Fox HH.Yap KB.McConville DH.O’Dell B.Lichtenstein BY.Schrock RR. J. Organomet. Chem. 1993, 459: 185
- 216c 
             
            Feldman J.Murdzek JS.Davis WM.Schrock RR. Organometallics 1989, 8: 2260
- 217 
             
            Nguyen ST.Grubbs RH.Ziller JW. J. Am. Chem. Soc. 1993, 115: 9858Reference Ris Wihthout Link
- 218 
             
            Trnka TM.Grubbs RH. Acc. Chem. Res. 2001, 34: 18
- 219a 
             
            Wu Z.Nguyen ST.Grubbs RH.Ziller JW. J. Am. Chem. Soc. 1995, 117: 5503
- 219b 
             
            Dias EL.Nguyen ST.Grubbs RH. J. Am. Chem. Soc. 1997, 119: 3887
- 219c 
             
            Aagaard OM.Meier RJ.Buda F. J. Am. Chem. Soc. 1998, 120: 7174
- 220a  
            Woodson CS, andGrubbs RH. inventors; Advanced Polymer Technologies WO 9729136. ; Chem. Abstr. 1997, 127, 206058Reference Ris Wihthout Link
- 220b  
            Woodson CS, andGrubbs RH. inventors; Advanced Polymer Technologies, WO 97200865. ; Chem. Abstr. 1997, 127, 81882Reference Ris Wihthout Link
- 221 
             
            Demonceau A.Stumpf AW.Saive E.Noels AF. Macromolecules 1999, 32: 2091
- 222a 
             
            Mohr B.Lynn DM.Grubbs RH. Organometallics 1996, 15: 4317
- 222b 
             
            Lynn DM.Mohr B.Grubbs RH. J. Am. Chem. Soc. 1998, 120: 1627
- 223a 
             
            Mayr M.Mayr B.Buchmeiser MR. Angew. Chem. Int. Ed. 2001, 40: 3839
- 223b 
             
            Kingsbury JS.Harrity JPA.Bonitatebus PJ.Hoveyda AH. J. Am. Chem. Soc. 1999, 121: 791
- 223c 
             
            Garber SB.Kingsbury JS.Gray BL.Hoveyda AH. J. Am. Chem. Soc. 2000, 122: 8168
- 223d 
             
            Kingsbury JH.Garber SB.Giftos JM.Gray BL.Okamoto MM.Farrer RA.Fourkas JT.Hoveyda AH. Angew. Chem. Int. Ed. 2001, 40: 4251
- 224a 
             
            Herrmann WA.Köcher C. Angew. Chem. Int. Ed. Engl. 1997, 36: 2163
- 224b 
             
            Huang J.Schanz H.-J.Stevens ED.Nolan SP. Organometallics 1999, 18: 5375
- 225a 
             
            Huang J.Stevens ED.Nolan SP.Peterson JL. J. Am. Chem. Soc. 1999, 121: 2674Reference Ris Wihthout Link
- 225b 
             
            Scholl M.Trnka TM.Morgan JP.Grubbs RH. Tetrahedron Lett. 1999, 40: 2247Reference Ris Wihthout Link
- 225c 
             
            Fürstner A.Thiel OL.Ackermann L.Schanz H.-J.Nolan SP. J. Org. Chem. 2000, 65: 2204Reference Ris Wihthout Link
- 226a 
             
            Scholl M.Ding S.Lee CW.Grubbs RH. Org. Lett. 1999, 1: 953Reference Ris Wihthout Link
- 226b 
             
            Chatterjee AK.Morgan JP.Scholl M.Grubbs RH. J. Am. Chem. Soc. 2000, 122: 3783Reference Ris Wihthout Link
- 227 
             
            Bielawski CW.Grubbs RH. Angew. Chem. Int. Ed. 2000, 39: 2903Reference Ris Wihthout Link
- 228 
             
            Weskamp T.Schattenmann WC.Spiegler M.Herrmann WA. Angew. Chem. Int. Ed. 1998, 37: 2490Reference Ris Wihthout Link
- 229 
             
            Weskamp T.Kohl FJ.Hieringer W.Gleich D.Herrmann WA. Angew. Chem. Int. Ed. 1999, 38: 2416
- 230a 
             
            Randl S.Gessler S.Wakamatsu H.Blechert S. Synlett 2001, 430Reference Ris Wihthout Link
- 230b 
             
            Wakamatsu H.Blechert S. Angew. Chem. Int. Ed. 2002, 41: 794Reference Ris Wihthout Link
- 231 
             
            Hansen SM.Volland MAO.Rominger F.Eisenträger F.Hofmann P. Angew. Chem. Int. Ed. 1999, 38: 1273
References
Large scale availability of P(cyclo-C6H11)2Cl has been announced.
183Obtaining fast rates in Heck reactions has been reviewed see: ref. [152a] p 3019-3036.
 
    