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Synlett 2022; 33(16): 1575-1581
DOI: 10.1055/a-1840-5199
DOI: 10.1055/a-1840-5199
synpacts
Visible-Light-Induced Organocatalyzed [2+1] Cyclization of Alkynes and (Trifluoroacetyl)silanes
We are grateful to NSFC (21901191), Fundamental Research Funds for the Central Universities, and Wuhan University for financial support.
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.
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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