Visible-light-promoted phosphine-mediated synthesis of thioesters and thioalkynes from sodium arylsulfinates

Abstract

We herein report a facile method to access thioesters and thioalkynes via a visible-light-promoted phosphine-mediated radical deoxyfunctionalization of sodium arylsulfinates with activated acids and iodoalkynes, respectively. The introduction of acid additives could facilitate the generation of arylthiyl radicals via tuning the equilibrium between arylsulfinate salts and the corresponding sulfinic acids, which favours the formation of thioesters while disfavouring the formation of thioalkynes. This protocol also features readily available starting materials, good functional group tolerance and practical applicability, for example, in the late-stage functionalization of non-steroidal anti-inflammatory drugs (NSAIDs).