Synthesis of Thioethers via Nickel-Catalyzed Cross-Coupling of Aryl Halides with Ketene Dithioacetal

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-09 DOI:10.1021/acs.orglett.4c04692

Baolong Xu, Shaowen Ling, Shuaichen Zheng, Xinyi Feng, Hui Liu, Yunhui Dong, Xinjin Li, Biqiong Hong, Feng-Gang Sun

引用次数: 0

Abstract

Herein, we present a nickel-catalyzed C–S cross-coupling between aryl halides and ketene dithioacetals under “base-free” conditions without an exogenous ligand. By employing easily available ketene dithioacetals as sulfide donors, this reaction affords a broad range of unsymmetrical alkyl-aryl sulfides without using odorous and toxic thiols. The newly developed catalytic methodology features an excellent functional group tolerance, wide substrate scope, and diverse downstream synthesis. Preliminary mechanism investigations reveal that a Ni(I)/Ni(III) catalytic cycle might be involved.

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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.