Synthesis of Cyclopropenols Enabled by Visible-Light-Induced Organocatalyzed [2+1] Cyclization

Although the synthesis of common cyclopropenes has been well studied, the access to cyclopropenols is rather limited. Herein, we report the first synthesis of alpha-trifluoromethylated cyclopropenols via 2+1 cycloaddition reactions between alkynes and trifluoroacylsilanes, enabled by visible-light-induced organocatalysis. The novel ambiphilic donor-acceptor carbenes derived from trifluoroacetylsilanes reacted efficiently with both activated and non-activated alkynes. The reaction features simple operation, mild conditions, broad substrate scope and good functional group tolerance. The synthetic potential of the reaction is highlighted by the gram-scale reactions and first synthesis of alpha-trifluoromethylated cyclopropanols through the combination of the 2+1 cyclization and high diastereoselective hydrogenation reaction in one pot.

Automated summary

This paper reports the first synthesis of alpha-trifluoromethylated cyclopropenols through visible-light-induced organocatalysis. The method offers simple operation, mild conditions, broad substrate scope, and good functional group tolerance.