Base-catalyzed stereoselective thiosulfonylation of ynones for the facile synthesis of thio-functionalized vinyl sulfones

The first catalytic vicinal thiosulfonylation of ynones has been developed. Under the catalysis of 1-20 mol% Cs2CO3, various ynones underwent the Michael addition/nucleophilic substitution tandem reaction with different thiosulfonates to form C-SO2 and C-S bonds simultaneously and produced thio-functionalized vinyl sulfones in high yields and with excellent E-selectivity. In addition, on using K3PO4 as the base, ynones can couple with trifluoromethyl thiosulfonates through a similar tandem process to afford the corresponding trifluoromethylthiolated products in good to high yields with excellent stereoselectivity.

Automated summary

The first catalytic vicinal thiosulfonylation of ynones has been successfully achieved, resulting in the formation of C-SO2 and C-S bonds simultaneously. This was accomplished through a Michael addition/nucleophilic substitution tandem reaction between ynones and various thiosulfonates. The reaction exhibited excellent selectivity and high yields.