Nickel-Catalyzed Cross-Electrophile Vinylation of α-Chloro Phosphonates

Herein, we report a general and efficient Ni-catalyzed reductive cross-coupling reaction of substituted vinyl bromides and α-chloro phosphonates to access a set of α-vinyl phosphonates using zinc as the terminal reductant. This reaction exhibits broad substrate adaptability and good functional group tolerance, which allows to afford diverse compounds including structurally complex motifs from natural products and drugs. Furthermore, the practicality was certificated through the gram-scale and transformation experiments. The preliminary mechanistic investigations support a radical chain process. The potential to realize enantiomeric control makes it more valuable for further exploration.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-10-18
DOI
https://doi.org/10.1021/acs.joc.4c01929
Citations
2
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.42

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article

Nickel-Catalyzed Cross-Electrophile Vinylation of α-Chloro Phosphonates

Tian Xie, Yang Ye, Liwei Wang, Huimin Yang et al.
2 citations
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
0.42
article

Nickel-Catalyzed Cross-Electrophile Vinylation of α-Chloro Phosphonates

Tian Xie, Yang Ye, Liwei Wang, Huimin Yang, Liang Zou
article en
2 citations

Abstract

Herein, we report a general and efficient Ni-catalyzed reductive cross-coupling reaction of substituted vinyl bromides and α-chloro phosphonates to access a set of α-vinyl phosphonates using zinc as the terminal reductant. This reaction exhibits broad substrate adaptability and good functional group tolerance, which allows to afford diverse compounds including structurally complex motifs from natural products and drugs. Furthermore, the practicality was certificated through the gram-scale and transformation experiments. The preliminary mechanistic investigations support a radical chain process. The potential to realize enantiomeric control makes it more valuable for further exploration.

The Journal of Organic ChemistryVol. 89(21)
Hangzhou Normal University (CN)
National Natural Science Foundation of China, Hangzhou Normal University, Department of Education of Zhejiang Province, Medical Science and Technology Project of Zhejiang Province
Openalex Percentile: Top 42%
Fluorine in Organic Chemistry
0.42
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Nickel-Catalyzed Cross-Electrophile Vinylation of α-Chloro Phosphonates — Tian Xie, Yang Ye, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS