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Activation of Si-Si Bonds for Copper(I)-Catalyzed Conjugate Silylation.

ABSTRACT: Several alkyl- and vinylsilanes were prepared through the copper(I)-catalyzed conjugate silylation of ?,?-unsaturated compounds. Optimal reaction conditions were first investigated to realize the conjugate addition of a nucleophilic silicon species to poorly electrophilic acceptors such as phenylvinyl sulfone by cleavage of the Si-Si bond of a disilane reagent. The scope of this reaction was extended to various electrophiles bearing different electron-withdrawing groups and afforded the desired substituted alkyl- and vinylsilanes. Among the wide range of commercially available disilanes, the reactivities of alkyl-, aryl-, and ethoxydisilane were also examined.

SUBMITTER: Iannazzo L

PROVIDER: S-EPMC3510700 | biostudies-literature | 2012 Sep

REPOSITORIES: biostudies-literature

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Activation of Si-Si Bonds for Copper(I)-Catalyzed Conjugate Silylation.

Iannazzo Laura L Molander Gary A GA

European journal of organic chemistry 20120901 26

Several alkyl- and vinylsilanes were prepared through the copper(I)-catalyzed conjugate silylation of α,β-unsaturated compounds. Optimal reaction conditions were first investigated to realize the conjugate addition of a nucleophilic silicon species to poorly electrophilic acceptors such as phenylvinyl sulfone by cleavage of the Si-Si bond of a disilane reagent. The scope of this reaction was extended to various electrophiles bearing different electron-withdrawing groups and afforded the desired ...[more]

PMID: 23204924

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