Visible-light-induced radical C(sp3)–S coupling for the synthesis of cyanoalkyl thioethers†

IF 4.6 1区 化学 Q1 CHEMISTRY, ORGANIC
Zhi-Qiang Zhu, Xiao-Wen Zheng, Dong-Liang Zhang, Xiao-Long Huang, Qian-Qian Xu, Zong-Bo Xie and Zhang-Gao Le
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引用次数: 0

Abstract

Herein, visible-light-driven radical–radical cross-coupling for the construction of a C(sp3)–S bond to afford various cyanoalkyl thioethers through EDA complex-promoted C–C and C–H bond cleavage is described. The photoactivation of a transiently assembled chromophore between thiolate anions and cycloketone oxime esters is critical to the generation of the C(sp3)–S bond. Notably, we also realize the in situ formed EDA complex-mediated 1,3-hydrogen atom transfer (HAT) to construct diverse thioethers under the standard conditions. This synthetic method features easily available substrates, a wide substrate scope, and mild reaction conditions, and has potential to be used for the preparation of valuable sulfides.

Abstract Image

可见光诱导自由基C(sp3)-S偶联合成氰基烷基硫醚
本文描述了可见光驱动自由基-自由基交叉偶联,通过EDA配合物促进C-C和C- h键的裂解,构建C(sp3)-S键,提供各种氰烷基硫醚。硫代阴离子与环酮肟酯之间的瞬时组装发色团的光活化对C(sp3)-S键的生成至关重要。值得注意的是,我们还实现了原位形成的EDA络合物介导的1,3-氢原子转移(HAT),以在过渡金属和无光催化剂的条件下构建多种硫醚。该合成方法具有底物易得、底物范围广、反应条件温和等特点,具有用于制备有价硫化物的潜力。
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来源期刊
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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