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

IF 3.3 2区 化学 Q1 CHEMISTRY, ORGANIC
Liang Zou, Huimin Yang, Tian Xie, Li-Wei Wang, Yang Ye
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引用次数: 0

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.

Abstract Image

镍催化的 α-氯膦酸盐的交-亲电乙烯基化反应
在此,我们报告了一种通用、高效的镍催化还原交叉偶联反应,该反应以锌为末端还原剂,通过取代的乙烯基溴化物和 α-氯膦酸盐获得一组 α-乙烯基膦酸盐。该反应具有广泛的底物适应性和良好的官能团耐受性,可以制备多种化合物,包括来自天然产品和药物的结构复杂的基团。此外,通过克级和转化实验证明了该反应的实用性。初步的机理研究支持自由基链过程。实现对映体控制的潜力使其更具有进一步探索的价值。
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来源期刊
The Journal of Organic Chemistry
The Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: The Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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