Non-directed oxidative annulation of 2-arylindazoles with electron deficient olefins via visible light photocatalysis

Abstract

A new visible-light-mediated non-directed oxidative annulation between 2-arylindazoles and electron-deficient olefins using commercially available piperidine-1-sulfonyl chloride as the radical precursor to afford fused 5,6-dihydroindazolo[2,3-a]quinolines has been developed under mild reaction conditions. This transformation occurs via two consecutive C–H bond functionalizations. The mechanistic investigation results indicate that the reaction progresses through a radical pathway forming a 2-(2-aryl-2H-indazol-3-yl)-3-piperidin-1-ylsulfonyl derivative as an intermediate.