RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2005(14): 2287-2292
DOI: 10.1055/s-2005-870013
DOI: 10.1055/s-2005-870013
PAPER
© Georg Thieme Verlag Stuttgart · New YorkPalladium-Phosphinous Acid Catalyzed Cross-Coupling of Aryl Halides Using a Hypervalent Phenylsilane in Water
Weitere Informationen
Received
28 February 2005
Publikationsdatum:
13. Juli 2005 (online)
Publikationsverlauf
Publikationsdatum:
13. Juli 2005 (online)
Abstract
A palladium-phosphinous acid catalyzed NaOH-promoted cross-coupling methodology that affords biaryls from tetrabutylammonium triphenyldifluorosilicate and aryl halides in good to high yields has been developed. The coupling proceeds in aqueous 0.5 M NaOH solution in the absence of organic co-solvents and does not require inert atmosphere, which greatly facilitates operation and catalyst handling.
Key words
biaryls - cross-coupling - silicon - palladium - catalysis
- 1a
Suzuki A. J. Organomet. Chem. 1999, 576: 147 - 1b
Grushin VV.Alper H. Top. Organomet. Chem. 1999, 3: 193 - 1c
Firooznia F.Gude C.Chan K.Satoh Y. Tetrahedron Lett. 1998, 39: 3985 - 1d
Littke AF.Dai C.Fu GC. J. Am. Chem. Soc. 2000, 122: 4020 - 1e
Tsukamoto H.Sato M.Kondo Y. Chem. Commun. 2004, 1200 - 2a
Dai C.Fu G. J. Am. Chem. Soc. 2001, 123: 2719 - 2b
Wolfe JP.Singer RA.Yang BH.Buchwald SL. J. Am. Chem. Soc. 1999, 121: 9550 - 3a
Huang J.Nolan SP. J. Am. Chem. Soc. 1999, 121: 9889 - 3b
Yamamura M.Moritani I.Murahashi SI. J. Organomet. Chem. 1975, 91: C39 - 3c
Megishi E. Metal Catalyzed Cross-Coupling Reactions Wiley-VCH; Weinheim: 1998. p.13-65 - 4a
Littke AF.Fu GC. J. Org. Chem. 1999, 64: 10 - 4b
Heck RF. Palladium Reagents in Organic Synthesis Academic Press; London: 1990. - 4c
Beletskaya IP.Cheprakov AV. Chem. Rev. 2000, 100: 3009 - 4d
de Meijere A.Meyer FE. Angew. Chem., Int. Ed. Engl. 1995, 33: 2379 - 4e
Schnyder A.Aemmer T.Indolese AF.Pittlekow U.Studer M. Adv. Synth. Catal. 2002, 344: 495 - 5a
Casado AL.Espinet P. J. Am. Chem. Soc. 1998, 120: 8978 - 5b
Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508 - 5c
Farina V.Krishnamurthy V.Scott WJ. Org. React. (N. Y.) 1997, 50: 1 - 5d
Bedford RB.Cazin CSJ.Hazalwood SM. Chem. Commun. 2002, 32: 2608 - 7a
Andrus MB.Song C. Org. Lett. 2001, 3: 3761 - 7b
Littke AF.Dai C.Fu GC. J. Am. Chem. Soc. 2000, 122: 4020 - 7c
Fu GC.Littke AF. Angew. Chem. Int. Ed. 2002, 41: 4176 - 7d
Littke AF.Schwarz L.Fu GC. J. Am. Chem. Soc. 2002, 124: 6343 - 7e
Su W.Urgaonkar S.Verkade JG. Org. Lett. 2004, 6: 1421 - 7f
Walker SD.Barder TE.Martinelli JR.Buchwald SL. Angew. Chem. Int. Ed. 2004, 43: 1871 - 7g
Schnyder A.Indolese AF.Studer M.Blaser HU. Angew. Chem. Int. Ed. 2002, 41: 3668 - 8a
Freeman GG. Silicones: An Introduction to Their Chemistry and Applications Chapel River Press; UK: 1962. p.99-104 - 8b
Hatanaka Y.Hiyama T. Synlett 1991, 845 - 9a
Lee J.-Y.Fu GC. J. Am. Chem. Soc. 2003, 125: 5616 - 9b
Nishihara Y.Ando J.Kato T.Mori A.Hiyama T. Macromolecules 2000, 33: 2779 - 10a
DeShong P.Mowery MJ. J. Org. Chem. 1999, 64: 1684 - 10b
Mowery ME.DeShong P. Org. Lett. 1999, 1: 2137 - 10c
Lee HM.Nolan SP. Org. Lett. 2000, 2: 2053 - 10d
Mowery MJ.DeShong P. J. Org. Chem. 1999, 64: 3266 - 11a
Lee HM.Nolan SP. Org. Lett. 2000, 2: 2053 - 11b
DeShong P.Handy CJ.Mowery M. Pure Appl. Chem. 2000, 72: 1655 - 11c
Riggleman S.DeShong P. J. Org. Chem. 2003, 68: 8106 - 12a
Badone D.Baroni M.Cardamone R.Ielmini A.Guzzi U. J. Org. Chem. 1997, 62: 7170 - 12b
Uozomi Y.Danjo H.Hayashi T. J. Org. Chem. 1999, 64: 3384 - 12c
Gelpke AES.Veerman JJN.Goedheijt MS.Kamer PCJ.van Leeuwen PWNM.Hiemstra H. Tetrahedron 1999, 55: 6657 - 12d
Paetzold E.Oehme G. J. Mol. Catal. A: Chem. 2000, 152: 69 - 12e
LeBlond CR.Andrews AT.Sun Y.Sowa JR. Org. Lett. 2001, 3: 1555 - 12f
Shaughnessy KH.Booth RS. Org. Lett. 2001, 3: 2757 - 12g
Dupuis C.Adiey K.Charruault L.Michelet V.Savignac M.Genet J.-P. Tetrahedron Lett. 2001, 42: 6523 - 12h
Ueda M.Nishimura M.Miyaura N. Synlett 2000, 856 - 12i
Botella L.Nájera C. Angew. Chem. Int. Ed. 2002, 41: 179 - 12j
Botella L.Nájera C. J. Organomet. Chem. 2002, 663: 46 - 12k
Alonso DA.Nájera C.Pacheco MA. J. Org. Chem. 2002, 67: 5588 - 12l
Bedford RB.Blake ME.Butts CP.Holder D. Chem. Commun. 2003, 466 - 12m
Li C.-J. Angew. Chem. Int. Ed. 2003, 42: 4856 - 13
Wuellner G.Jaensch H.Kannenberg S.Schubert F.Boche G. Chem. Commun. 1998, 1509 - 14a
Amatore C.Blart E.Genet JP.Jutand A.Lemaire-Audoire S.Savignac M. J. Org. Chem. 1995, 60: 6829 - 14b
Hessler A.Stelzer O.Dibowski H.Worm K.Schmidtchen FP. J. Org. Chem. 1997, 62: 2362 - 14c
Lopez-Deber MP.Castedo L.Granja JR. Org. Lett. 2001, 3: 2823 - 15a
Roshchin AI.Bumagin NA.Beletskaya IP. Tetrahedron Lett. 1995, 36: 125 - 15b
Rai R.Aubrecht KB.Collum DB. Tetrahedron Lett. 1995, 36: 3111 - 15c
Kang S.-K.Baik T.-G.Song S.-Y. Synlett 1999, 327 - 16
Genet JP.Blart E.Savignac M. Synlett 1992, 715 - 17a
Genet PJ.Savignac M. J. Organomet. Chem. 1999, 576: 305 - 17b
Takami K.Yorimitsu H.Shinokubo H.Matsubara S.Oshima K. Org. Lett. 2001, 3: 1997 - 17c
Najera C.Gil-Molto J.Karlstrom S.Falvello LR. Org. Lett. 2003, 5: 1451 - 18a
Uozomi Y.Nakai Y. Org. Lett. 2002, 4: 2997 - 18b
Leadbeater NE.Marco M. J. Org. Chem. 2003, 68: 888 - 19a
Murata M.Suzuki K.Watanabe S.Masuda Y. J. Org. Chem. 1997, 62: 8569 - 19b
Murata S.Watanabe S.Masuda Y. Tetrahedron Lett. 1999, 40: 9255 - 19c
Denmark SE.Amishiro N. J. Org. Chem. 2003, 68: 6997 - 20a
Oi S.Honma Y.Inoue Y. Org. Lett. 2002, 4: 667 - 20b
Huang TS.Li CJ. Chem. Commun. 2001, 2348 - 20c
Murata M.Shimazaki R.Watanabe S.Masuda Y. Synthesis 2001, 2231 - 21a
Li GY. Angew. Chem. Int. Ed. 2001, 40: 1513 - 21b
Li GY.Zheng G.Noonan AF. J. Org. Chem. 2001, 66: 8677 - 21c
Li GY. J. Org. Chem. 2002, 67: 3643 - 21d
Wolf C.Lerebours R. J. Org. Chem. 2003, 68: 7077 - 21e
Wolf C.Lerebours R.Tanzini EH. Synthesis 2003, 2069 - 21f
Yang W.Wang Y.Corte JR. Org. Lett. 2003, 5: 3131 - 21g
Wolf C.Lerebours R. J. Org. Chem. 2003, 68: 7551 - 21h
Wolf C.Lerebours R. Org. Lett. 2004, 6: 1147 - 21i
Wolf C.Lerebours R. Org. Biomol. Chem. 2004, 2: 2161 - 22
Littke AF.Schwarz L.Fu GC. J. Am. Chem. Soc. 2002, 124: 6343 - 23
Riguet E.Alami M.Cahiez G. J. Organomet. Chem. 2001, 624: 376 - 24
Navarro O.Kelly RA.Nolan SP. J. Am. Chem. Soc. 2003, 125: 16194 - 25
Bei X.Turner HW.Weinberg WH.Guram AS. J. Org. Chem. 1999, 64: 6797 - 26
Mino T.Shirae Y.Sakamoto M.Fujita T. Synlett 2003, 882 - 27
Choudary BM.Madhi S.Chowdari NS.Kantam ML.Sreedhar B. J. Am. Chem. Soc. 2002, 124: 14127 - 28
Molander GA.Biolatto B. Org. Lett. 2002, 4: 1867 - 29
Karikomi M.Tsukada H.Toda T. Heterocycles 2001, 55: 1249 - 30
Song SJ.Cho SJ.Park DK.Kwon TW.Jenekhe SA. Tetrahedron Lett. 2003, 44: 255 - 31
Demir AS.Reis O.Emrullahoglu M. J. Org. Chem. 2004, 68: 578
References
Bond dissociation energies for PhX; X = Cl: 96 kcal/mol, X = Br: 81 kcal/mol, X = I: 65 kcal/mol.