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 2012(2): 272-282
DOI: 10.1055/s-0031-1289639
DOI: 10.1055/s-0031-1289639
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkThe Heck Reaction of Allylic Alcohols Catalysed by an Air-Stable Phosphinito Complex of Palladium(II)
Weitere Informationen
Received
8 September 2011
Publikationsdatum:
08. Dezember 2011 (online)
Publikationsverlauf
Publikationsdatum:
08. Dezember 2011 (online)
Abstract
The Heck coupling of aryl bromides with primary and secondary allylic alcohols, performed in the presence of an air-stable phosphinito complex of palladium(II), produced the corresponding carbonyl compounds. Reactions with tertiary allylic alcohols under the same conditions generated the aromatic conjugated alcohols.
Key words
allylic alcohols - Heck reaction - palladium - aldehydes - ketones
- 1a
Karimi B.Behzadnia H.Elhamifar D.Akhavan PF.Esfahani FK.Zamani A. Synthesis 2010, 1399 - 1b
Yin L.Liebscher J. Chem. Rev. 2007, 107: 133 - 1c
Muzrt J. Tetrahedron 2005, 61: 4179 - 1d
Fagnou K.Lautens M. Angew. Chem. Int. Ed. 2002, 41: 26 - 2a
Pan D.Jiao N. Synlett 2010, 1577 - 2b
Deagostino A.Prandi C.Tabasso S.Venturello P. Molecules 2010, 15: 2667 - 2c
Bellina F.Chiappe C. Molecules 2010, 15: 2211 - 2d
Narayanan R. Molecules 2010, 15: 2124 - 2e
Wu X.-F.Anbarasan P.Neumann H.Beller M. Angew. Chem. Int. Ed. 2010, 49: 9047 - 2f
Frost CG.Mutton L. Green Chem. 2010, 12: 1687 - 3a
Bergamini P.Bertolasi V.Cattabriga M.Ferretti V.Loprieno U.Mantovani N.Marvelli L. Eur. J. Inorg. Chem. 2003, 918 - 3b
Gebauer T.Frenzen G.Dehnicke K. Z. Kristallogr. 1995, 210: 539 - 3c
Ghaffar T.Kieszkiewicz A.Nyburg SC.Parkins AW. Acta Crystallogr., Sect. C 1994, 50: 697 - 3d
Dixon KR.Rattray AD. Can. J. Chem. 1971, 49: 3997 - 4
Jiménez-Bülle J.Gaviño R. Catal. Commun. 2008, 9: 826 - 5a
Naik DV.Palenik GJ.Jacobson S.Carty AJ.
J. Am. Chem. Soc. 1974, 96: 2286 - 5b
Carty AJ.Jacobson SE.Simpson RT.Taylor NJ. J. Am. Chem. Soc. 1975, 97: 7254 - 6a
Mastrorilli P.Latronico M.Nobile CF.Suranna GP.Fanizzi FP.Englert U.Ciccarella G. Dalton Trans. 2004, 1117 - 6b
Dixon KR.Rattray AD. Inorg. Chem. 1977, 16: 209 - 7
Wong EH.Bradley FC. Inorg. Chem. 1981, 20: 2333 - 8
Andrew J.Duncan S.Hedden D.Roundhill DM.Stephenson TA.Walkinshaw MD. Angew. Chem., Int. Ed. Engl. 1982, 21: 452 - 9a
Irvine DJ.Preston SA.Cole-Hamilton DJ.Barnes JC. J. Chem. Soc., Dalton Trans. 1991, 2412 - 9b
Gould RO.Jones CL.Sime WJ.Stephenson TA. J. Chem. Soc., Dalton Trans. 1977, 669 - 10
Roundhill DM.Sperline RP.Beaulieu WB. Coord. Chem. Rev. 1978, 26: 263 - 11
Beaulieu WB.Rauchfuss TB.Roundhill DM. Inorg. Chem. 1975, 14: 1732 - 12a
North M.Parkins AW.Shariff AN. Tetrahedron Lett. 2004, 45: 7625 - 12b
Jiang X.Minnaard AJ.Feringa BL.de Vries JG. J. Org. Chem. 2004, 69: 2327 - 12c
Papakyprianou A.Parkins AW.Prince PD.Steed JW. Org. Prep. Proced. Int. 2002, 34: 436 - 12d
Ghaffar T.Parkins AW. J. Mol. Catal. A: Chem. 2000, 160: 249 - 12e
Akisanya J.Parkins AW.Steed JW. Org. Process Res. Dev. 1998, 2: 274 - 12f
Ghaffar T.Parkins AW. Tetrahedron Lett. 1995, 36: 8657 - 13
Ahmed TJ.Fox BR.Knapp SMM.Yelle RB.Juliette JJ.Tyler DR. Inorg. Chem. 2009, 48: 7828 - 14
Han L.-B.Choi N.Tanaka M. Organometallics 1996, 15: 3259 - 15
Pryjomska I.Bartosz-Bechowski H.Ciunik Z.Trzeciak AM.Ziólkowski JJ. Dalton Trans. 2006, 213 - 16a
Boffi A.Cacchi S.Ceci P.Cirilli R.Fabrizi G.Prastaro A.Niembro S.Shafir A.Vallribera A. ChemCatChem 2011, 3: 347 - 16b
Satyanarayana G.Maier ME. Org. Lett. 2008, 10: 2361 - 16c
Berthiol F.Doucet H.Santelli M. Tetrahedron 2006, 62: 4372 - 16d
Berthiol F.Doucet H.Santelli M. Appl. Organomet. Chem. 2006, 20: 855 - 16e
Berthiol F.Doucet H.Santelli M. Tetrahedron Lett. 2004, 45: 5633 - 16f
Solabannavar SB.Helavi VB.Desai UV.Mane RB. Synth. Commun. 2003, 33: 361 - 16g
Bouquillon S.Ganchegui B.Estrine B.Hénin F.Muzart J. J. Organomet. Chem. 2001, 634: 153 - 16h
Zhao H.Cai M.-Z.Hu R.-H.Song A.-S. Synth. Commun. 2001, 31: 3665 - 16i
Watson SE.Taylor EC.Patel H. Synth. Commun. 1998, 28: 1897 - 16j
Tamaru Y.Yamada Y.Yoshida Z. Tetrahedron Lett. 1978, 919 - 16k
Tamaru Y.Yamada Y.Yoshida Z. Tetrahedron Lett. 1977, 3365 - 16l
Chalk AJ.Magennis SA. J. Org. Chem. 1976, 41: 1206 - 17a
Liu J.Zhu J.Jiang H.Wang W.Li J. Chem. Commun. 2010, 46: 415 - 17b
Li J.Mau A.Strauss CR. Chem. Commun. 1997, 1275 - 17c
Melpolder JB.Heck RF. J. Org. Chem. 1976, 41: 265 - 18a
Caló V.Nacci A.Monopoli A.Ferola V. J. Org. Chem. 2007, 72: 2596 - 18b
Mo J.Xu L.Ruan J.Liu S.Xia J. Chem. Commun. 2006, 3591 - 18c
Masllorens J.Bouquillon S.Roglans A.Hénin F.Muzart J. J. Organomet. Chem. 2005, 690: 3822 - 18d
Chalk AJ.Magennis SA. J. Org. Chem. 1976, 41: 273 - 19a
Voight EA.Yin H.Downing SV.Calad SA.Matsuhashi H.Giordano I.Hennessy AJ.Goodman RM.Wood JL. Org. Lett. 2010, 12: 3422 - 19b
Gaudin J.-M. Tetrahedron Lett. 1991, 32: 6113 - 20
Batt F.Gozzi C.Fache F. Chem. Commun. 2008, 5830 - 21a
Schlosser M.Mongin F. Chem. Soc. Rev. 2007, 36: 1161 - 21b
Rebstock A.-S.Mongin F.Trecourt F.Queguiner G. Org. Biomol. Chem. 2004, 2: 291 - 21c
French HE.Sears K. J. Am. Chem. Soc. 1951, 73: 469 - 21d
Gilman H.Spatz SM. J. Am. Chem. Soc. 1940, 62: 446 - 22a
Ferlin MG.Bortolozzi B.Brun O.Castagliuolo I.Hamel E.Basso G.Viola G. ChemMedChem 2010, 5: 1373 - 22b
Fand TI.Lutomski CP. J. Am. Chem. Soc. 1949, 71: 2931 - 22c
Burrus HO.Powell G. J. Am. Chem. Soc. 1945, 67: 1468 - 23a
Molinaro C.Shultz S.Roy A.Lau S.Trinh T.Angelaud R.O’Shea PD.Abele S.Cameron M.Corley E.Funel J.-A.Steinhuebel D.Weisel M.Krska S. J. Org. Chem. 2011, 76: 1062 - 23b
Tamaru Y.Yamada Y.Yoshida Z. J. Org. Chem. 1978, 43: 3396 - 24
Ambrogio I.Fabrizi G.Cacchi S.Henriksen ST.Fristrup P.Tanner D.Norrby P.-O. Organometallics 2008, 27: 3187