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Synthesis 2004(18): 3079-3083
DOI: 10.1055/s-2004-834896
DOI: 10.1055/s-2004-834896
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York
Nickel-Catalyzed Electrochemical Coupling of Aryl, Heteroaryl or Vinyl Halides with Activated Alkyl Chlorides: Synthetic and Stereochemical Aspects
Further Information
Received
2 September 2004
Publication Date:
02 November 2004 (online)
Publication History
Publication Date:
02 November 2004 (online)
Abstract
We report coupling reactions of aryl, heteroaryl or vinyl halides with activated alkyl halides, using nickel catalysis combined with an electrochemical process. Synthetic and stereochemical aspects are presented. This minireview highlights electrosynthesis in the field of synthesis and catalysis.
Key words
nickel - electrochemistry - aryl Halides - vinyl Halides - C-C coupling
- 1
Nédélec JY.Périchon J.Troupel M. Topics in Current Chemistry Springer-Verlag; Berlin / Heidelberg: 1997. p.185 - 2
Rollin Y.Troupel M.Tuck D.Périchon J. J. Organomet. Chem. 1986, 303: 131 -
3a
Schlegel B.Hänel F.Gollmick FA.Saluz H.-P.Gräfe U. J. Antibiotics 2003, 56: 917 -
3b
Kichiyama T, andYamada Y. inventors; Patent application., JP 1997-161087. , Chem. Abstr. 1997, 130, 153474 - 4
Chaussard J.Folest JC.Nédélec J.-Y.Périchon J.Sibille S.Troupel M. Synthesis 1990, 369 -
5a
Durandetti M.Sibille S.Nédélec J.-Y.Périchon J. Synth. Commun. 1994, 2: 145 -
5b
Durandetti M.Nédélec J.-Y.Périchon J. J. Org. Chem. 1996, 61: 1748 - 6
Brown HC.Nambu H.Rogic MM. J. Am. Chem. Soc. 1969, 91: 6852 - 7
Dell’Erba C.Novi M.Petrillo G.Tavani C. Tetrahedron 1994, 50: 3529 -
8a
Bakshi SP.Turner EE. J. Chem. Soc. 1961, 171 -
8b
Sock O.Troupel M.Périchon J. Tetrahedron Lett. 1985, 26: 1509 -
9a
Millard AA.Rathke MW. J. Am. Chem. Soc. 1977, 99: 4833 -
9b
Fauvarque JF.Jutand A. J. Organomet. Chem. 1979, 177: 273 -
9c
Klingstedt T.Frejd T. Organometallics 1983, 2: 598 - 10
Rieu JP.Boucherle A.Cousse H.Mouzin G. Tetrahedron 1986, 42: 4095 - 11
Shen TY. Angew. Chem., Int. Ed. Engl. 1972, 11: 460 -
12a
Durandetti M,Lachaise I,Nédélec J.-Y, andPérichon J. inventors; Patent application, FR 1997-7908. , Chem. Abstr. 1997, 130, 188492 -
12b
Durandetti M,Lachaise I,Nédélec J.-Y, andPérichon J. inventors; Patent application, WO 1998-FR1336. , Chem. Abstr. 1998, 130, 188492 -
12c
Durandetti M.Périchon J.Nédélec J.-Y. J. Org. Chem. 1997, 62: 7914 -
13a
Close WJ. J. Org. Chem. 1950, 15: 1131 -
13b
Roder H.Helmchen G.Peters EM.Peters K.von Schnering H.-G. Angew. Chem., Int. Ed. Engl. 1984, 23: 898 - 14
Wenkert E.Fernandes JB.Michelotti EL.Swindell CS. Synthesis 1983, 701 - 15
Kharash MS.Reinmuth O. Grignard Reactions of Nonmetallic Substances Coustable; London: 1954. -
16a
Bumagin NA.Kasatkin A.Beletskaya IP. Bull. Acad. Sci. USSR 1984, 33: 1696 -
16b
Tsuji J. Palladium Reagents and Catalysts Wiley; Chichester: 1995. p.290 - 17
Suzuki S.Shiono M.Fujita Y. Synthesis 1983, 804 -
18a
Zhu L.Wehmeyer RM.Rieke RD. J. Org. Chem. 1991, 56: 1445 -
18b
Dübner F.Knochel P. Angew. Chem. Int. Ed. 1999, 38: 379 -
19a
Gomes P,Gosmini C, andPérichon J. inventors; Patent application, FR 2001-08808. , Chem. Abstr. 2001, 138, 79947 -
19b
Gomes P.Gosmini C.Périchon J. J. Org. Chem. 2003, 68: 1142 -
20a
Schulz E.Fahmi K.Lemaire M. Acros Org. Acta 1995, 1: 10 -
20b
Roncali J. Chem. Rev. 1997, 97: 173 - 21
Gronowitz S. Ark. Kemi 1958, 12: 533 - 22
Durandetti M.Périchon J.Nédélec J.-Y. Tetrahedron Lett. 1997, 38: 8683 - 23
Mellah M.Labbé E.Nédélec J.-Y.Périchon J. New J. Chem. 2002, 26: 207 - 24
Cannes C.Condon S.Durandetti M.Périchon J.Nédélec J.-Y. J. Org. Chem. 2000, 65: 4575 - 25
Salamonczyk GM.Han K.Guo Z.-W.Sih CJ. J. Org. Chem. 1996, 61: 6893 -
26a
Iseki Y.Watanabe E.Mori A.Inoue S. J. Am. Chem. Soc. 1993, 115: 7313 -
26b
Angeloni L.Castellucci E.Bartocci G.Mazzucato U.Spalletti A.Marconi G. Gazz. Chim. Ital. 1996, 126: 609 -
26c
Chen C.-C.Pan K.Wang S.-L.Ho T.-I. J. Lumin. 1997, 71: 321