Visible-Light-Induced Organocatalyzed [2+1] Cyclization of Alkynes and (Trifluoroacetyl)silanes

Gang Zhou; Xiao Shen

doi:10.1055/a-1840-5199

Synlett, Table of Contents

Synlett 2022; 33(16): 1575-1581
DOI: 10.1055/a-1840-5199

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Visible-Light-Induced Organocatalyzed [2+1] Cyclization of Alkynes and (Trifluoroacetyl)silanes

Gang Zhou

,

Xiao Shen ∗

Abstract

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Abstract

The synthesis of common cyclopropenes has been widely studied, but the synthesis of cyclopropenols is a significant challenge. Here, we highlight our recent work on the synthesis of trifluoromethylated cyclopropenols through a [2+1] cycloaddition reaction between alkynes and (trifluoroacetyl)silanes under visible-light-induced organocatalysis. The novel amphiphilic donor–acceptor carbenes derived from (trifluoroacetyl)silanes can react effectively with both activated and nonactivated alkynes. A broad substrate scope and a good functional-group tolerance have been achieved. Moreover, the synthetic potential of this reaction was highlighted by a gram-scale reaction and the one-pot diastereoselective synthesis of trifluoromethylated cyclopropanols.

Key words

cyclopropenols - photocatalysis - organocatalysis - cyclopropanols - carbenes

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