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

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-12-05 DOI:10.1039/d4qo01994f

Zhi-Qiang Zhu, Xiao-Wen Zheng, Dong-Liang Zhang, Xiao-Long Huang, Qian-Qian Xu, Zong-Bo Xie, Zhang-Gao Le

引用次数: 0

Abstract

Herein, visible-light-driven radical-radical cross-coupling for the construction of 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 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 transtion-metal- and photocatalyst-free conditions. This synthetic method features easily available substrates, wide substrate scope, and mild reaction conditions, which has potential to be used for the preparation of valuable sulfides.

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来源期刊

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.