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

Chemistry. 2022 Mar 10;28(15):e202104080. doi: 10.1002/chem.202104080. Epub 2022 Feb 23.

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 CF3 SO2 Na or CF2 HSO2 Na as coupling partners further achieves three-component fluoromethyl-arylation of vinyl ethers, furnishing a series of valuable CF3 /CF2 H-incorporated alkyl heterocycles under mild conditions.

Keywords: alkenes; catalyst-free reactions; difunctionalization; electron-donor-acceptor complex; radical cascade.