Photocatalyst-Free Visible-Light-Mediated Synthesis of β-(Trifluoromethyl)alkenyl Ketoximes Using 2-Bromo-3,3,3-trifluoropropene as a Radical Precursor

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-02 DOI:10.1021/acs.orglett.6c03861

Yibo Shi, Ningning Gong, Xin Xin, Xiaobing Liu, Wenguang Li, Weiguang Kong, Yongqi Yu, Heyun Sheng, Ting Li

引用次数: 0

Abstract

We report a photocatalyst-free, visible-light-mediated difunctionalization of alkenes employing 2-bromo-3,3,3-trifluoropropene (BTP) as a radical precursor. This protocol operates under mild conditions using potassium formate as an electron transfer reagent and tert-butyl nitrite (TBN) as a hydrogen atom transfer (HAT) reagent, enabling efficient β-(trifluoromethyl)alkenyl ketoxime synthesis. Notably, no photocatalyst or transition metal is required, yet excellent stereoselectivity of the conjugated terminal alkene is achieved. Furthermore, this method exhibits a broad substrate scope and good functional group tolerance, accommodating diverse alkene classes.

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以2-溴-3,3,3-三氟丙烯为自由基前体的无光催化-可见光介导合成β-（三氟甲基）烯基酮肟

摘要：我们报道了以2-溴-3,3,3-三氟丙烯（BTP）为自由基前体的无光催化剂、可见光介导的烯烃双官能化反应。该方案在温和条件下使用甲酸钾作为电子转移试剂，亚硝酸盐叔丁基（TBN）作为氢原子转移（HAT）试剂，实现了高效的β-（三氟甲基）烯基酮肟合成。值得注意的是，不需要光催化剂或过渡金属，但共轭末端烯烃具有优异的立体选择性。此外，该方法具有广泛的底物范围和良好的官能团耐受性，可容纳多种烯烃类。

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.