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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.

Authors :
Zhang, Yanhu
Ren, Ziyang
Liu, Yun‐Lin
Wang, Zhentao
Li, Zhaodong
Source :
European Journal of Organic Chemistry. 8/31/2020, Vol. 2020 Issue 32, p5192-5200. 9p.
Publication Year :
2020

Abstract

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. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
1434193X
Volume :
2020
Issue :
32
Database :
Academic Search Index
Journal :
European Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
145402513
Full Text :
https://doi.org/10.1002/ejoc.202000782