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Fluoroalkylation of Allylic Alcohols with Concomitant (Hetero)aryl Migration: Access to Fluoroalkylated Ketones and Evaluation of Antifungal Action against Magnaporthe grisea
Author(s) -
Zhang Yanhu,
Ren Ziyang,
Liu YunLin,
Wang Zhentao,
Li Zhaodong
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.202000782
Subject(s) - chemistry , aryl , antifungal , allylic rearrangement , ketone , iodide , organic chemistry , combinatorial chemistry , medicinal chemistry , stereochemistry , catalysis , alkyl , microbiology and biotechnology , biology
Fluoroalkyl(hetero)arylation of allylic alcohols with perfluoroalkyl iodide or difluoroacetic acid as fluoroalkyl source was developed herein, delivering functionalized ketones containing an α‐quaternary center. Formation of the fluoroalkyl radical was followed by its intermolecular addition to alkenes and the migration of a (hetero)aryl group with the concomitant generation of a ketone group to finish the domino sequence. Mechanistic studies indicated that the aryl migration proceeded through neophyl rearrangement in a radical pathway. Moreover, preliminary antifungal evaluation against Magnaporthe grisea is also described for the first time.