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Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins.

ABSTRACT: Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes to provide functionalized allylbenzene derivatives are described. A wide range of both the benzyl chloride and alkene coupling partners are tolerated. In contrast to analogous palladium-catalyzed variants of this process, all reactions described herein employ electronically unbiased aliphatic olefins (including ethylene), proceed at room temperature, and provide 1,1-disubstituted olefins over the more commonly observed 1,2-disubstituted olefins with very high selectivity.

SUBMITTER: Matsubara R

PROVIDER: S-EPMC3226728 | biostudies-literature | 2011 Nov

REPOSITORIES: biostudies-literature

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Nickel-catalyzed Heck-type reactions of benzyl chlorides and simple olefins.

Matsubara Ryosuke R Gutierrez Alicia C AC Jamison Timothy F TF

Journal of the American Chemical Society 20111108 47

Nickel-catalyzed intermolecular benzylation and heterobenzylation of unactivated alkenes to provide functionalized allylbenzene derivatives are described. A wide range of both the benzyl chloride and alkene coupling partners are tolerated. In contrast to analogous palladium-catalyzed variants of this process, all reactions described herein employ electronically unbiased aliphatic olefins (including ethylene), proceed at room temperature, and provide 1,1-disubstituted olefins over the more common ...[more]

PMID: 22066899

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