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

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

Publication History

Received: 29 March 2022

Accepted after revision: 01 May 2022

Accepted Manuscript online:
01 May 2022

Article published online:
07 June 2022

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