<i>N</i> -Phenylhydroxylamine-InducedRadical Relay for the Synthesis of α-TrifluoromethylKetones

Abstract Herein, we report a previously unexplored N-phenylhydroxylamine-induced radical relay strategy for the synthesis of α-trifluoromethyl ketones from readily available alkynes and Togni’s reagent. This protocol features a broad substrate scope, high functional group tolerance, operational simplicity, and scalability. Mechanistic studies reveal that N-phenylhydroxylamine plays a key role in facilitating the radical relay process. Furthermore, the late-stage functionalization of biologically relevant molecules highlights the synthetic utility of this method for the preparation of structurally diverse α-CF3 ketones.

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Publication Details

Journal
Organic Letters
Published
2026-08-17
DOI
https://doi.org/10.1021/acs.orglett.6c03090
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

N -Phenylhydroxylamine-InducedRadical Relay for the Synthesis of α-TrifluoromethylKetones

Hongyin Gao, Rui-Qiang Jiao, Changping Tian
Organic Letters
Fluorine in Organic Chemistry
article

N -Phenylhydroxylamine-InducedRadical Relay for the Synthesis of α-TrifluoromethylKetones

Hongyin Gao, Rui-Qiang Jiao, Changping Tian
article en

Abstract

Abstract Herein, we report a previously unexplored N-phenylhydroxylamine-induced radical relay strategy for the synthesis of α-trifluoromethyl ketones from readily available alkynes and Togni’s reagent. This protocol features a broad substrate scope, high functional group tolerance, operational simplicity, and scalability. Mechanistic studies reveal that N-phenylhydroxylamine plays a key role in facilitating the radical relay process. Furthermore, the late-stage functionalization of biologically relevant molecules highlights the synthetic utility of this method for the preparation of structurally diverse α-CF3 ketones.

Organic Letters
Shandong University (CN), Ningxia University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Ningxia Province, Taishan Scholar Project of Shandong Province
Openalex Percentile: Top 11%
Fluorine in Organic Chemistry
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