Metal-Free Tunable 1,2-Difunctionalization of Terminal Alkynes: Synthesis of β-Substituted α,β-Unsaturated Ketones

A metal-free tunable 1,2-difunctionalization of the terminal alkynes showcasing a tandem installation of C-C and C-S bonds has been developed. The key enabling factor for the approach is the use of acetic acid as an acyl source to synthesize beta-substituted alpha,beta-unsaturated ketones. The reaction at room temperature leads to the regioselective acylation at the terminal carbon of alkynes, whereas at -78 degree celsius, the acylation occurs at the more substituted carbon.

Automated summary

A metal-free approach for tunable 1,2-difunctionalization of terminal alkynes, involving tandem installation of C-C and C-S bonds, has been developed. The key factor enabling this approach is the use of acetic acid as an acyl source to synthesize beta-substituted alpha,beta-unsaturated ketones. The reaction at different temperatures results in regioselective acylation at the terminal carbon and the more substituted carbon of the alkynes respectively.