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Activation of Si–Si Bonds for Copper(I)‐Catalyzed Conjugate Silylation
Author(s) -
Iannazzo Laura,
Molander Gary A.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200767
Subject(s) - chemistry , electrophile , silylation , alkyl , nucleophile , aryl , conjugate , reagent , catalysis , disilane , medicinal chemistry , organic chemistry , silicon , mathematics , mathematical analysis
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 substituted alkyl‐ and vinylsilanes. Among the wide range of commercially available disilanes, the reactivities of alkyl‐, aryl‐, and ethoxydisilane were also examined.