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

Abstract

An efficient and practical method for highly regio- and stereo-selective cyanosulfonylation of allenes by inserting sulfur dioxide to synthesize useful (E)-α-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.