Copper catalyzed cyano-sulfonylation of allenes via the insertion of sulfur dioxide toward the synthesis of (E)-α-cyanomethyl vinylsulfones

An efficient and practical method for highly regio- and stereo-selective cyanosulfonylation of allenes by inserting sulfur dioxide to synthesize useful (E)-alpha-cyanomethyl vinylsulfones has been explored. This strategy features mild experimental conditions and good substrate compatibility. Interestingly, SOgen displayed a higher reactivity than other SO2 surrogates. The obtained products could be further transformed into other valuable compounds. The preliminary mechanism studies indicate that the reaction may go through a radical pathway.

Automated summary

An efficient and practical method for highly regio- and stereo-selective cyanosulfonylation of allenes using sulfur dioxide has been explored. The reaction conditions are mild and the substrate compatibility is good. Interestingly, the SOgen reagent showed higher reactivity compared to other SO2 surrogates. The obtained products can be further transformed into valuable compounds. Preliminary mechanism studies suggest a radical pathway for the reaction.