Photoredox/Copper-Cocatalyzed Difluoromethylation of Benzylic Bromides with PPh <sub>3</sub> (CF <sub>2</sub> H) <sub>2</sub>

We describe a general copper/photoredox-cocatalyzed difluoromethylation of benzyl bromides using PPh<sub>3</sub>(CF<sub>2</sub>H)<sub>2</sub> as a reagent. This protocol exhibits a broad substrate scope, good yields, and high functional group compatibility. The Cu(I) species first activates the benzylic C-Br bond to form a benzyl radical and then scavenges a CF<sub>2</sub>H radical to form a Cu(III) species. The facile reductive elimination from the Cu(III) center enables the coupling of the CF<sub>2</sub>H radical with the C(sp<sup>3</sup>) fragment.

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Publication Details

Journal
Organic Letters
Published
2026-01-05
DOI
https://doi.org/10.1021/acs.orglett.5c04233
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Photoredox/Copper-Cocatalyzed Difluoromethylation of Benzylic Bromides with PPh 3 (CF 2 H) 2

Kaiteng Wang, Hao Song, Jingwen Li, Le Liu et al.
Organic Letters
Fluorine in Organic Chemistry
article

Photoredox/Copper-Cocatalyzed Difluoromethylation of Benzylic Bromides with PPh 3 (CF 2 H) 2

Kaiteng Wang, Hao Song, Jingwen Li, Le Liu, Yulong Wang, Xin-Hua Duan, Shanben Yin, Mingyou Hu
article en

Abstract

We describe a general copper/photoredox-cocatalyzed difluoromethylation of benzyl bromides using PPh<sub>3</sub>(CF<sub>2</sub>H)<sub>2</sub> as a reagent. This protocol exhibits a broad substrate scope, good yields, and high functional group compatibility. The Cu(I) species first activates the benzylic C-Br bond to form a benzyl radical and then scavenges a CF<sub>2</sub>H radical to form a Cu(III) species. The facile reductive elimination from the Cu(III) center enables the coupling of the CF<sub>2</sub>H radical with the C(sp<sup>3</sup>) fragment.

Organic LettersVol. 28(2)
Shihezi University (CN), Centre for Sustainable Energy (GB), Sustainable Energy Systems (United Kingdom) (GB), Xi'an Jiaotong University (CN)
Openalex Percentile: Top 95%
Fluorine in Organic Chemistry
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