On-water synthesis of 3,6-dihydro-2H-thiopyrans: Doyle–Kirmse reaction induced by blue-LEDs and ring-closing metathesis

Abstract

A metal-free system for Doyle–Kirmse reaction of biologically important diallyl sulfide with donor–acceptor diazo compounds in an aqueous medium using blue-LED irradiation was demonstrated. The resulting sulfanyl dienes were converted into thiopyrans using ring-closing metathesis in water. Additionally, the utility of dihydro-thiopyrans was also investigated.