Halide-free and metal-free allylic thiolation/selenation of P(O)H compounds with sulfur/selenium and allylic alcohols

Abstract

A halide-free and metal-free strategy for the construction of C–S/Se–P(O) bonds through a three-component reaction of allylic alcohols, P(O)H compounds, and elemental sulfur/selenium is reported. This protocol eliminates the requirement for using toxic, odorous and moisture-sensitive starting materials, as well as the need for pre-functionalization of substrates. Moreover, this transformation demonstrates high compatibility with various allylic alcohols and P(O)H compounds at a strict ratio of 1 : 1 : 1. Based on controlled experiments, a reaction mechanism involving an allyl carbocation was proposed.