Gold(I)-Catalyzed Carbothiolation via Rearrangement of S-Propargyl Group: An Access to 3-Allenyl or 3-Indenyl Benzo[b]thiophenes,Advanced Synthesis & Catalysis

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Gold(I)-Catalyzed Carbothiolation via Rearrangement of S-Propargyl Group: An Access to 3-Allenyl or 3-Indenyl Benzo[b]thiophenes
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-11-08 , DOI: 10.1002/adsc.202201000
Camille Van Wesemael ₁ , Nicolas Brach ₁ , Mihaela Gulea ₁ , Gaëlle Blond ₂

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A series of 3-allenyl benzo[b]thiophenes were synthesized through a gold(I)-catalyzed domino reaction. The process consists in a 5-endo-dig cyclization with C−S bond formation and consecutive S-to-C propargyl migration via [3,3]-sigmatropic Claisen rearrangement. With aryl substituents on both triple bonds of the substrate, subsequent intramolecular hydroarylation on the formed allenyl system led to 3-indenyl benzo[b]thiophenes. From a substrate bearing a 3-butynol moiety diverse fused O-heterocycles have been obtained via intramolecular hydroalkoxylation. A gold-mediated 1,3-migration involving allenyl to propargyl rearrangement is also described.

中文翻译：

通过重排 S-炔丙基基团的金 (I)-催化硫醇化：获得 3-丙二烯基或 3-茚基苯并[b]噻吩

通过金（I）催化的多米诺骨牌反应合成了一系列3-烯基苯并[b]噻吩。该过程包括 5-endo-dig 环化与 CS 键形成和通过 [3,3]-sigmatropic Claisen 重排的连续 S-to-C 炔丙基迁移。在底物的两个三键上都有芳基取代基，随后在形成的丙二烯基系统上进行分子内加氢芳基化，生成 3-茚基苯并[b]噻吩。从带有 3-丁炔醇部分的底物，通过分子内加氢烷氧基化获得了多种稠合的 O-杂环。还描述了金介导的 1,3-迁移，涉及烯基到炔丙基重排。

更新日期：2022-11-08

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