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N-Heterocyclic Olefin Catalyzed Silylation and Hydrosilylation Reactions of Hydroxyl and Carbonyl Compounds

Uǧur Kaya, Uyen P. N. Tran, Dieter Enders, Junming Ho and Thanh V. Nguyen*

*School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia, t.v.nguyenunsw.edu.au

U. Kaya, U. P. N. Tran, D. Enders, J. Ho, T. V. Nguyen, Org. Lett., 2017, 19, 1398-1401.

DOI: 10.1021/acs.orglett.7b00306 (free Supporting Information)



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Abstract

N-Heterocyclic olefins (NHOs) are promising organocatalysts with strong nucleophilicity and Brønsted basicity. NHOs are efficient promoters for a direct dehydrogenative silylation of alcohols or hydrosilylation of carbonyl compounds. Preliminary results of an asymmetric dehydrogenative silylation are also discussed.

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proposed mechanism



Key Words

Silylethers, organocatalysis


ID: J54-Y2017