高对映体选择性脱羧二氟甲基化反应

IF 14.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Journal of the American Chemical Society Pub Date : 2024-10-15 DOI:10.1021/jacs.4c11257

Xian Zhao, Chao Wang, Lingfeng Yin, Wei Liu

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引用次数: 0

摘要

在立体中心含有二氟甲基（CF2H）的有机氟分子在制药领域的重要性日益凸显，这是因为 CF2H 基团具有独特的亲脂性氢键供体能力。尽管 CF2H 基团具有潜力，但将其对映选择性地安装到容易获得的起始材料中仍然是一个具有挑战性且开发不足的领域。在本研究中，我们报告了一种镍催化的脱羧二氟甲基化反应，该反应以优异的对映选择性将烷基羧酸转化为二氟甲基化产物。这种镍催化反应具有广泛的官能团耐受性，适用于合成生物相关分子的氟化生物异构体。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Highly Enantioselective Decarboxylative Difluoromethylation

Organofluorine molecules that contain difluoromethyl groups (CF₂H) at stereogenic centers have gained importance in pharmaceuticals due to the unique ability of CF₂H groups to act as lipophilic hydrogen bond donors. Despite their potential, the enantioselective installation of CF₂H groups into readily available starting materials remains a challenging and underdeveloped area. In this study, we report a nickel-catalyzed decarboxylative difluoromethylation reaction that converts alkyl carboxylic acids into difluoromethylated products with exceptional enantioselectivity. This Ni-catalyzed protocol exhibits broad functional group tolerance and is applicable for synthesizing fluorinated bioisosteres of biologically relevant molecules.

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来源期刊

Journal of the American Chemical Society 化学-化学综合

CiteScore

24.40

自引率

6.00%

发文量

2398

审稿时长

1.6 months

期刊介绍： The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.