Borane‐Catalyzed Reductive α‐Silylation of Conjugated Esters and Amides Leaving Carbonyl Groups Intact |
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| Authors: | Youngchan Kim Prof?Dr Sukbok Chang |
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| Affiliation: | 1. Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST), Deajeon 305‐701 (Korea);2. Center for Catalytic Hydrocarbon Functionalizations, Institute for Basic Science (IBS), Deajeon 305‐701 (Korea) |
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| Abstract: | Described herein is the development of the B(C6F5)3‐catalyzed hydrosilylation of α,β‐unsaturated esters and amides to afford synthetically valuable α‐silyl carbonyl products. The α‐silylation occurs chemoselectively, thus leaving the labile carbonyl groups intact. The reaction features a broad scope of both acyclic and cyclic substrates, and the synthetic utility of the obtained α‐silyl carbonyl products is also demonstrated. Mechanistic studies revealed two operative steps: fast 1,4‐hydrosilylation of conjugated carbonyls and then slow silyl group migration of a silyl ether intermediate. |
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| Keywords: | boron chemoselectivity conjugation hydrosilylation reaction mechanisms |
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