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钯催化 - 芳基硫代甲酸酯作为硫酯源的α,β-不饱和硫代酯的硫羰基化合成。

Palladium-Catalyzed Thiocarbonylative Synthesis of α,β-Unsaturated Thioesters Using -Aryl Thioformates as the Thioester Sources.

机构信息

Department of Chemistry, Key Laboratory of Surface & Interface Science of Polymer Materials of Zhejiang Province, Zhejiang Sci-Tech University, Hangzhou, Zhejiang 310018, People's Republic of China.

Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning 116023, People's Republic of China.

出版信息

Org Lett. 2023 Jun 9;25(22):4140-4144. doi: 10.1021/acs.orglett.3c01400. Epub 2023 May 25.

DOI:10.1021/acs.orglett.3c01400
PMID:37227073
Abstract

A palladium-catalyzed thiocarbonylation reaction for the synthesis of α,β-unsaturated thioesters from vinyl triflates with -aryl thioformates as the thioester sources has been developed. The reaction proceeded smoothly at low temperature, and a variety of α,β-unsaturated thioesters were produced in moderate to high yields with very good functional group tolerance. This protocol features mild reaction conditions, good substrate scope, and avoids the use of toxic CO gas or odorous thiols, which made it a worthy addition to α,β-unsaturated thioester synthesis via a thioester transfer process.

摘要

钯催化的硫羰化反应,用于从乙烯基三氟甲磺酸酯与芳基硫代甲酸酯作为硫酯源合成α,β-不饱和硫代酯。该反应在低温下顺利进行,各种α,β-不饱和硫代酯以中等至高产率得到,具有很好的官能团耐受性。该方法具有温和的反应条件、良好的底物范围,并且避免了使用有毒的 CO 气体或有臭味的硫醇,这使得它成为通过硫酯转移过程合成α,β-不饱和硫代酯的一种很有价值的方法。

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