Photoinduced Cross-Coupling of Trifluoromethylarenes with Heteroarenes via Unactivated C(sp3)–F and C(sp2)–H Selective Cleavage

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-12-17 DOI:10.1021/acs.orglett.4c04420

Jiyao Zhang, Yuxiang Zhang, Lebin Qian, Zhijun Zuo

引用次数: 0

Abstract

The installation of gem-difluoromethylene groups into two adjacent aryl groups is a formidable synthetic challenge despite their attractive structural, physical, and biochemical properties. Herein, we disclose a photoredox-catalyzed selective defluoroarylation of heteroarenes through inert C(sp³)–F and C(sp²)–H selective cleavage, which provides a straightforward route to access medicinally relevant aryl–heteroaryl or heteroaryl–heteroaryl difluoromethane scaffolds. Salient features of this reaction include readily accessible starting materials, metal-free conditions, and broad substrate scope.

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在两个相邻的芳基中加入二氟亚基是一项艰巨的合成挑战，尽管它们具有诱人的结构、物理和生物化学特性。在此，我们揭示了一种通过惰性 C(sp3)-F 和 C(sp2)-H 选择性裂解的光氧化催化杂芳基的选择性脱氟芳基化反应，为获得具有药用价值的芳基-杂芳基或杂芳基-杂芳基二氟甲烷支架提供了一条直接的途径。该反应的显著特点包括容易获得的起始材料、无金属条件和广泛的底物范围。

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.