Cobalt-catalyzed cross-coupling reactions of alkyl halides with aryl Grignard reagents and their application to sequential radical cyclization/cross-coupling reactions

Reactions of alkyl halides with arylmagnesium bromides in the presence of cobalt(II)(diphosphine) complexes are discussed. Treatment of 1-bromooctane with phenylmagnesium bromide with the aid of a catalytic amount of CoCl 2(dppp) [DPPP=1,3-bis(diphenylphosphino)propane] yielded octylbenzene in good...

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Published inTetrahedron Vol. 62; no. 10; pp. 2207 - 2213
Main Authors Ohmiya, Hirohisa, Wakabayashi, Katsuyu, Yorimitsu, Hideki, Oshima, Koichiro
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 06.03.2006
Elsevier
Subjects
Aryl Grignard reagent
Chemistry
Chemistry, Organic
Cobalt
Cross-coupling reaction
Physical Sciences
Radical reaction
Science & Technology
Radical reaction
Cross-coupling reaction
Aryl Grignard reagent
Cobalt
cross-coupling reaction
aryl Grignard reagent
radical reaction
cobalt
LIGNANS
ACETALS
BROMIDES
ALKENYLATION
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Summary:Reactions of alkyl halides with arylmagnesium bromides in the presence of cobalt(II)(diphosphine) complexes are discussed. Treatment of 1-bromooctane with phenylmagnesium bromide with the aid of a catalytic amount of CoCl 2(dppp) [DPPP=1,3-bis(diphenylphosphino)propane] yielded octylbenzene in good yield. The reaction mechanism would include single electron transfer from an electron-rich cobalt complex to alkyl halide to generate the corresponding alkyl radical. The mechanism was justified by CoCl 2(dppe)-catalyzed [DPPE=1,2-bis(diphenylphosphino)ethane] sequential radical cyclization/cross-coupling reactions of 6-halo-1-hexene derivatives that yielded benzyl-substituted cyclopentane skeletons. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.12.013