Site-Selective Copper–N-Heterocyclic Carbene-Catalyzed C(sp2)–C(sp) Cross-Coupling of Aryl Thianthrenium Salts

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-03-23 DOI:10.1021/acs.orglett.5c00875

Jin Zhang, Hang Yang, Li Sun, Yan Guo, Gaopeng Zhang, Ruihong Wang, Michal Szostak

引用次数: 0

Abstract

This work demonstrates Cu–NHC (NHC = N-heterocyclic carbene) catalyzed alkynylation of aryl thianthrenium salts via thiazol-2-ylidene ligands, achieving a Pd-free Sonogashira coupling with broad substrate compatibility and functional group tolerance. Late-stage pharmaceutical alkynylation and rare alkynylative C–H functionalization/ring-opening pathways are enabled. Thiazol-2-ylidenes, featuring a “half-umbrella”-shaped geometry, exhibit superior catalytic performance over traditional imidazol-2-ylidenes, underscoring their unique ligand efficacy. Cu–NHC catalysis enables the use of aryl thianthrenium salts as versatile electrophiles for diverse cross-couplings under mild conditions.

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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.