Catalyst‐Free Intermolecular Sulfonyl/Fluoromethyl Heteroarylation of Vinyl Ethers via Visible‐Light‐Induced Charge Transfer

Abstract

We report a visible‐light‐induced three‐component sulfonyl‐heteroarylation of vinyl ethers with sulfinates and five‐membered heteroaryl chlorides. This protocol proceeds via electron‐donor‐acceptor (EDA) complexes between sulfinates and heteroaryl chlorides, giving β‐sulfonyl alkyl five‐membered heteroarenes with high efficiency and excellent regioselectivity under mild and catalyst‐free conditions. Utilization of CF3SO2Na or CF2HSO2Na as coupling partners further achieves three‐component fluoromethyl‐arylation of vinyl ethers, furnishing a series of valuable CF3/CF2H‐incorporated alkyl heterocycles under mild conditions.

Catalyst-free photoarylation reactions promoted by visible light

“…Later on, Chu and co-workers reported a similar methodology consisting of a sulfonative heteroarylation of vinyl ethers 59 (Scheme 35). 116 In this three-component reaction, visible light irradiation of EDA complexes, formed by the aggregation of electron-rich sulfinates 55 and electron-poor heteroaryl chlorides 58 , led to the formation of various β-sulfonyl alkyl heteroarenes 60 in up to 90% yield. When the protocol was extended to sodium difluoromethanesulfinate (CF 2 HSO 2 Na) as the coupling substrate, the corresponding β-CF 2 H alkyl heteroarenes were obtained in up to 71% yield.…”