Cobalt-Catalyzed Fluoroalkylation Carbonylation of Unactivated Alkenes via Distal Aryl Migration

A cobalt-catalyzed trifluoromethylation carbonylation of unactivated alkenes via distal aryl migration has been developed, enabling the highly regioselective synthesis of trifluoroalkylated 1,4-diketones. This method operates under mild conditions and exhibits broad functional group compatibility. In addition, the protocol can be extended to the difluoroalkylative carbonylation of unactivated alkenes. The synthetic utility of this method has been demonstrated by scalable synthesis and further transformations of the products into diverse fluoroalkylated heteroarenes. Mechanistic investigations support a radical pathway with distal aryl migration.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-11-03
DOI
https://doi.org/10.1021/acs.joc.5c02385
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00
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article

Cobalt-Catalyzed Fluoroalkylation Carbonylation of Unactivated Alkenes via Distal Aryl Migration

Donghao Jiang, Li‐Jie Cheng, Wei Li, Mengdie Xiao
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

Cobalt-Catalyzed Fluoroalkylation Carbonylation of Unactivated Alkenes via Distal Aryl Migration

Donghao Jiang, Li‐Jie Cheng, Wei Li, Mengdie Xiao
article en

Abstract

A cobalt-catalyzed trifluoromethylation carbonylation of unactivated alkenes via distal aryl migration has been developed, enabling the highly regioselective synthesis of trifluoroalkylated 1,4-diketones. This method operates under mild conditions and exhibits broad functional group compatibility. In addition, the protocol can be extended to the difluoroalkylative carbonylation of unactivated alkenes. The synthetic utility of this method has been demonstrated by scalable synthesis and further transformations of the products into diverse fluoroalkylated heteroarenes. Mechanistic investigations support a radical pathway with distal aryl migration.

The Journal of Organic ChemistryVol. 90(45)
Hunan University (CN)
Openalex Percentile: Top 74%
Fluorine in Organic Chemistry
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