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Synthesis 2002(13): 1903-1911
DOI: 10.1055/s-2002-33918
DOI: 10.1055/s-2002-33918
PAPER
© Georg Thieme Verlag Stuttgart · New York
Stereospecific Synthesis of 3,3-Disubstituted Acrylonitriles by Heck Reaction
Further Information
Received
30 April 2002
Publication Date:
09 September 2002 (online)
Publication History
Publication Date:
09 September 2002 (online)
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Abstract
The coupling reaction of 3-aryl (or heteroaryl) acrylonitriles with several aryl and heteroaryl iodides (Heck reaction) under Jeffery’s conditions has been studied as a concept to synthesize, in a stereospecific manner, trisubstituted olefins.
Key words
arylations - Heck reaction - heterocycles - Palladium catalysis - alkenes
-
1a
Heck RF. Acc. Chem. Res. 1979, 12: 146 -
1b
Heck RF. Org. React. (N.Y.) 1982, 27: 345 -
1c
Heck RF. Vinyl Substitutions with Organopalladium Intermediates, In Comprehensive Organic Synthesis Vol. 4:Trost BM.Fleming I. Pergamon; Oxford: 1991. Chap. 4.3. -
1d
De Meijere A.Meyer FE. Angew. Chem., Int. Ed. Engl. 1994, 33: 2379 -
1e
Cabri W.Candiani I. Acc. Chem. Res. 1995, 28: 2 -
1f
Negishi E.Copéret C.Ma S.Liou S.Liu F. Chem. Rev. 1996, 96: 365 -
1g
Crisp GT. Chem. Soc. Rev. 1998, 27: 427 -
1h
Beletskaya IP.Cheprakov AV. Chem Rev. 2000, 100: 3009 -
1i
Whitcombe NJ.Kuok Hii K.Gibson SE. Tetrahedron 2001, 57: 7449 - For examples of β-arylation of 1,2-disubstituted electron-poor olefins, see:
-
2a
Amorese A.Arcadi A.Bernocchi E.Cacchi S.Cerrini S.Fedeli W.Ortar G. Tetrahedron 1989, 45: 813 -
2b
Moreno-Mañas M.Pérez M.Pleixats R. Tetrahedron Lett. 1996, 37: 7449 -
2c
Arcadi A.Cacchi S.Fabrizi G.Marinelli F.Pace P. Tetrahedron 1996, 52: 6983 -
2d
Moreno-Mañas M.Pleixats R.Roglans A. Synlett 1997, 1157 -
2e
Gürtler C.Buchwald SL. Chem.-Eur. J. 1999, 5: 3107 -
2f
Littke AF.Fu GC. J. Am. Chem. Soc. 2001, 123: 6989 -
2g
Calò V.Nacci A.Monopoli A.Lopez L.di Cosmo A. Tetrahedron 2001, 57: 6071 -
2h
Battistuzzi G.Cacchi S.Fabrizi G. Synlett 2002, 439 -
2i For Heck reaction of 3-arylacrylates supported
on a soluble polymeric support, see:
Blettner CG.König WA.Stenzel W.Schotten T. Tetrahedron Lett. 1999, 40: 2101 -
2j For double Heck arylation
of acrylates under high-pressure and high-temperature conditions,
see:
Sugihara T.Takebayashi M.Kaneko C. Tetrahedron Lett. 1995, 36: 5547 -
2k For an attractive and efficient
stereoselective one-pot double Heck arylation of 2-pyridyldimethyl(vinyl)silanes,
see:
Itami K.Nokami T.Ishimura Y.Mitsudo K.Kamei T.Yoshida J. J. Am. Chem. Soc. 2001, 123: 11577 - 3
Togni A.Hayashi T. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science VCH; Weinheim: 1995. -
4a
Almansa C.Gómez LA.Cavalcanti FL.de Arriba AF.Rodríguez R.Carceller E.García-Rafanell J.Forn J. J. Med. Chem. 1996, 39: 2197 -
4b
Almansa C,Carceller E,González CS,Torres MC, andBartroli J. inventors; J. Uriach and Cia, S.A.; Eur. Pat. EP 669, 333. ; Chem. Abstr. 1995, 123, 340129u -
4c
Blank B.Zuccarello WA.Cohen SR.Frishmuth GJ.Scaricaciottoli D. J. Med. Chem. 1969, 12: 271 -
4d
Ohnishi H,Miyakoshi M,Isozaki M,Fijitake M,Mikami N,Yanoshita R,Akasofu H,Sugizaki K, andNakata N. inventors; Terumo Corp., Japan; Eur. Pat. Appl. EP 501876. ; Chem. Abstr. 1993, 118, 6872 - 5
Mourot D.Patin H. J. Organomet. Chem. 1976, 114: 89 - 6
Jeffery T. Tetrahedron 1996, 52: 10113 - 7
Kasahara A.Izumi T.Maemura M. Bull. Chem. Soc. Jpn. 1977, 50: 1021 - 8
Sévignon M.Papillo J.Schulz E.Lemaire M. Tetrahedron Lett. 1999, 40: 5873 - 9
Handbook of Chemistry and
Physics
63rd ed:
CRC Press Inc.;
Boca
Raton:
1982-1983.
- 10
DiBiase SA.Lipisko BA.Haag A.Wolak RA.Gokel GW. J. Org. Chem. 1979, 44: 4640 - 11
Dolter RJ.Curran C. J. Am. Chem. Soc. 1960, 82: 4153 - 12
Claisse JA,Gregory GI, andWarburton WK. inventors; US Patent 4012377. ; Chem. Abstr. 1978, 87, 39491 - 13
Todres ZV.Ermekov DS. J. Organomet. Chem. 1989, 369: 371 - 14
Kasahara A.Izumi T.Ogihara T. J. Heterocycl. Chem. 1989, 26: 597 - 15
Imrie C.Loubser C.Engelbrecht P.McCleland CW. J. Chem. Soc., Perkin Trans. 1 1999, 2513 - 16
Ishikawa F. Chem. Pharm. Bull. 1980, 28: 1394