An operationally simple protocol for the stereoselective synthesis of functionally and structurally diverse succinimides using readily accessible aza-1,6-enynes. The strategy relies on the use of visible-light-mediated photocatalysis with a readily available 4CzIPN photocatalyst.

Abstract

Succinimides are an essential structural component of many natural products, clinical drug molecules, and pharmacophores, but are challenging to synthesize difunctionalized succinimides in a single operational step. In this study, we report an operationally simple protocol for the stereoselective synthesis of functionally and structurally diverse succinimides using readily accessible aza-1,6-enynes. The strategy relies on the of use visible-light-mediated photocatalysis with a readily available 4CzIPN photocatalyst. The mechanism of this reaction is believed to proceed through a radical cascade seleno/thiosulfonation of aza-1,6- enynes in an atom-economic and stereoselective manner. The reaction's advantageous features are operational simplicity, metal/oxidant/base-free, complete atom economy, and excellent functional group tolerance with broad substrate scope.