Dual Intermolecular Allylic C-H Functionalization within the Tetrasubstituted Alkene Scaffold

Activation of chloramine-T (TsNNaCl) with Brønstedt acid generates an active reagent for the double allylic C-H functionalization of tetrasubstituted alkenes under intermolecular reaction control. The reaction generates a carbon-nitrogen and a carbon-chlorine bond, respectively, and proceeds with complete regio- and chemoselectivity. A total of 14 examples demonstrate the applicability of the dual C-H functionalization process. The mechanism involves the intermediary participation of a 1,3-butadiene derivative, which can also be employed directly as substrates.