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Fanke Meng, Hwanjong Jang and Prof. Amir H. Hoveyda Exceptionally E- and β-Selective NHC–Cu-Catalyzed Proto-Silyl Additions to Terminal Alkynes and Site- and Enantioselective Proto-Boryl Additions to the Resulting Vinylsilanes: Synthesis of Enantiomerically Enriched Vicinal and Geminal Borosilanes Chemistry - A European Journal 19

Version of Record online: 16 JAN 2013 | DOI: 10.1002/chem.201203803

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Different NHCs for different tasks: Three classes of N-heterocyclic carbene(NHC)–Cu complexes serve to promote two sets of reactions. Catalysts with an achiral monodentate NHC convert terminal alkynes to (E)-β-vinylsilanes with exceptional selectivity through efficient protosilylation. Cu-based catalysts bearing a chiral monodentate NHC bring about protoborations of alkyl-substituted vinylsilanes, generating enantiomerically enriched vicinal borosilanes; however, it is the sulfonate-bridged bidentate NHC–Cu complexes that deliver geminal silylborons with the highest e.r. values.

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