Gold-Catalyzed Deallylative C–S Cross-Coupling Reactions

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-05-01 DOI:10.1021/acs.orglett.5c01321

Prafulla Bera, Tanmayee Nanda, Nayan A. Barhate, Manoj V. Mane, Nitin T. Patil

引用次数: 0

Abstract

Herein, we report the gold-catalyzed deallylative C–S cross-coupling reaction through ligand-enabled Au(I)/Au(III) redox catalysis. One of the major challenges in gold-catalyzed C–S cross-coupling reactions is to prevent catalyst deactivation caused by the formation of a strong gold–sulfur bond. We discovered that the use of allyl phenyl sulfide as a sulfur surrogate facilitates a dynamic equilibrium between cationic Au(I) and Au(I)-sulfide complexes, overcoming the gold quenching problem. A detailed mechanistic investigation, including ³¹P NMR studies, mass analysis, and stoichiometric experiments, provided valuable insights into the reaction mechanism, which is further supported by computational studies.

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金催化的C-S交叉偶联反应

在此，我们报道了通过配体激活Au(I)/Au（III）氧化还原催化的金催化的脱溶性C-S交叉偶联反应。金催化C-S交叉偶联反应的主要挑战之一是防止因形成强金-硫键而引起的催化剂失活。我们发现，使用烯丙基苯基硫化物作为硫代物，促进了阳离子Au(I)和Au(I)-硫化物配合物之间的动态平衡，克服了金的猝灭问题。详细的机理研究，包括31P核磁共振研究、质量分析和化学计量学实验，为反应机理提供了有价值的见解，这进一步得到了计算研究的支持。

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.