Pd-Catalyzed 1,4-Difluoromethylative Functionalization of 1,3-Dienes Using Freon-22

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-10-15 DOI:10.1021/acs.orglett.4c03338

Qixin Zhou, Jing Wang, Tiancen Bian, Yan Liang, Weikang Yan, Liejin Zhou, Zuxiao Zhang

引用次数: 0

Abstract

We report a visible-light-driven, palladium-catalyzed 1,4-difluoromethylative functionalization of conjugated dienes using chlorodifluoromethane (ClCF₂H, Freon-22) as a cost-effective difluoromethyl source. The excited palladium catalyst efficiently reduces the C–Cl bond, which generates a CF₂H radical, followed by regioselective S_N2’ substitution to afford 1,4-difunctionalized products. This versatile, redox-neutral method accommodates diverse nucleophiles and exhibits broad functional group compatibility, making it suitable for late-stage functionalization in drug discovery and offering a direct route to difluoromethylated molecules.

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使用氟利昂-22 的 Pd 催化 1,3-二烯的 1,4-二氟甲基功能化反应

我们报告了一种可见光驱动的钯催化 1,4-二氟甲基化共轭二烯官能化方法，该方法使用氯二氟甲烷（ClCF2H，氟利昂-22）作为具有成本效益的二氟甲基源。激发的钯催化剂能有效还原 C-Cl 键，生成 CF2H 自由基，然后进行区域选择性 SN2'取代，得到 1,4-二官能化产物。这种多功能、氧化还原中性的方法适用于不同的亲核物，并具有广泛的官能团兼容性，因此适用于药物发现的后期官能化，并提供了获得二氟甲基化分子的直接途径。

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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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.