Nickel-Catalyzed Direct Fluorosulfonylation of Vinyl Bromides and Benzyl Bromides for Sulfonyl Fluorides

An efficient nickel-catalyzed direct fluorosulfonylation of vinyl bromides and benzyl bromides under mild reaction conditions has been developed for sulfonyl fluorides utilizing Na<sub>2</sub>S<sub>2</sub>O<sub>4</sub> and NFSI as the sulfur dioxide and fluorine sources, respectively. This reaction system tolerates organic bromide compounds, such as β-styryl bromides, alkyl vinyl bromides, and benzyl bromides, to achieve corresponding sulfonyl fluorides in moderate to good yields, with convenient operation, mild conditions, broad substrate scope, good functional group compatibility, and excellent retention of configuration to vinyl bromides.

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Publication Details

Journal
Organic Letters
Published
2024-11-08
DOI
https://doi.org/10.1021/acs.orglett.4c03820
Citations
2
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.42

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article

Nickel-Catalyzed Direct Fluorosulfonylation of Vinyl Bromides and Benzyl Bromides for Sulfonyl Fluorides

Changge Zheng, Kui Zhao, Ruilong Feng, Xiaoyu Wang et al.
2 citations
Organic Letters
Fluorine in Organic Chemistry
0.42
article

Nickel-Catalyzed Direct Fluorosulfonylation of Vinyl Bromides and Benzyl Bromides for Sulfonyl Fluorides

Changge Zheng, Kui Zhao, Ruilong Feng, Xiaoyu Wang, Chongbin Wei, Feng Zheng, Chunxiang Li, Jianquan Hong, Xifei Chen, Xinxin Gong
article en
2 citations

Abstract

An efficient nickel-catalyzed direct fluorosulfonylation of vinyl bromides and benzyl bromides under mild reaction conditions has been developed for sulfonyl fluorides utilizing Na<sub>2</sub>S<sub>2</sub>O<sub>4</sub> and NFSI as the sulfur dioxide and fluorine sources, respectively. This reaction system tolerates organic bromide compounds, such as β-styryl bromides, alkyl vinyl bromides, and benzyl bromides, to achieve corresponding sulfonyl fluorides in moderate to good yields, with convenient operation, mild conditions, broad substrate scope, good functional group compatibility, and excellent retention of configuration to vinyl bromides.

Organic LettersVol. 26(46)
Jiangnan University (CN)
National Natural Science Foundation of China, Fundamental Research Funds for the Central Universities
Clean water and sanitation
Openalex Percentile: Top 41%
Fluorine in Organic Chemistry
0.42
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Nickel-Catalyzed Direct Fluorosulfonylation of Vinyl Bromides and Benzyl Bromides for Sulfonyl Fluorides — Changge Zheng, Kui Zhao, et al. · Organic Letters (2024) | TGRS Research Map | TGRS