Catalyst‐Free Intermolecular Sulfonyl/Fluoromethyl Heteroarylation of Vinyl Ethers via Visible‐Light‐Induced Charge Transfer. Issue 15 (23rd February 2022)

• Record Type: Journal Article
• Authors: Long, Tianyu; Pan, Shiwei; Zhu, Shengqing; Chu, Lingling
• Is Part Of: Chemistry. Volume 28:Issue 15(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-02-23
• Subjects: alkenes -- catalyst-free reactions -- difunctionalization -- electron-donor-acceptor complex -- radical cascade; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202104080
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : A visible‐light‐induced three‐component sulfonyl‐heteroarylation of vinyl ethers with sulfinates and five‐membered heteroaryl chlorides is reported. This protocol proceeds via a photoinduced electron transfer process of electron‐donor‐acceptor complex between sulfinates and heteroaryl chlorides, enabling facile excess to β‐sulfonyl and β‐fluoromethyl α‐oxy alkyl heteroaromatics under mild and catalyst‐free conditions.