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One‐Step Synthesis of Trifluoroethylated Chromones via Radical Cascade Cyclization–Coupling of 2‐(Allyloxy)arylaldehydes
Author(s) -
Gao Fei,
Meng FanXiao,
Du JiYuan,
Zhang Shiyan,
Huang HongLi
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201901636
Subject(s) - chemistry , radical cyclization , cascade , reagent , trifluoromethyl , combinatorial chemistry , cascade reaction , organic chemistry , medicinal chemistry , catalysis , alkyl , chromatography
A transition‐metal‐free synthetic protocol involved with trifluoromethyl radical addition–cyclization of 2‐(allyloxy)arylaldehydes for a series of CF 3 ‐containing 3‐substituted chromenones formation has been developed. The radical cascade cyclization–coupling reaction can be run in a one‐step manner with Langlois′ reagent (CF 3 SO 2 Na) and K 2 S 2 O 8 . Broad scopes of substrates with various functional groups are evaluated in moderate to good efficacy under operational simplicity and mild reaction conditions. A plausible mechanism for the construction of trifluoroethylated chromones is proposed based on mechanistic studies.