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Visible‐Light‐Induced Radical Cascade Cyclizations of 1,7‐Enynes with Sulfinic Acids: Direct Access to Sulfonated Chromanes and Sulfonated Tetrahydroquinolines under Metal‐Free Conditions
Author(s) -
Liu Qi,
Mei Yousheng,
Wang Lei,
Ma Yongmin,
Li Pinhua
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000846
Subject(s) - chemistry , sulfinic acid , functional group , visible spectrum , cascade , eosin y , photochemistry , metal , photocatalysis , combinatorial chemistry , organic chemistry , catalysis , chromatography , physics , optoelectronics , polymer
Abstract Visible‐light‐induced strategy to access sulfonated chromanes and sulfonated 1,2,3,4‐tetrahydroquinolines via a radical cascade cyclization of 1‐(arylethynyl)‐2‐(vinyloxy)benzenes and N ‐allyl‐2‐(arylethynyl)anilines with aromatic and aliphatic sulfinic acids has been developed. In the presence of TBHP (7.5 mol%) as an oxidant and Eosin Y (3.0 mol%) as a photocatalyst, the reactions undergo smoothly to afford the corresponding products in good yields at room temperature under metal‐free conditions. This transformation features low loading of TBHP, mild reaction conditions, simple operation, broad functional‐group tolerance, and good yields of products.