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可见光促进亚磺酸钠生成硫自由基:硫自由基与硫酯的自由基-自由基偶联反应

Visible-Light-Promoted Thiyl Radical Generation from Sodium Sulfinates: A Radical-Radical Coupling to Thioesters.

作者信息

Bogonda Ganganna, Patil Dilip V, Kim Hun Young, Oh Kyungsoo

机构信息

Center for Metareceptome Research, College of Pharmacy , Chung-Ang University , 84 Heukseok-ro , Dongjak, Seoul 06974 , Republic of Korea.

出版信息

Org Lett. 2019 May 17;21(10):3774-3779. doi: 10.1021/acs.orglett.9b01218. Epub 2019 May 7.

Abstract

A convenient visible-light photoredox catalysis has been developed for the synthesis of thioesters from two readily available starting materials: acid chlorides and sodium sulfinates. The facile generation of acyl radical species under the visible light photoredox conditions allows the formation of thiyl radical species from sodium sulfinates via multiple single electron transfer reactions, where the final acyl radical-thiyl radical coupling has been accomplished. The direct radical-radical coupling strategy offers a mild and controlled photochemical approach to important synthetic building blocks such as thioesters.

摘要

一种便捷的可见光光氧化还原催化方法已被开发出来,用于从两种容易获得的起始原料:酰氯和亚磺酸钠合成硫酯。在可见光光氧化还原条件下,酰基自由基物种的轻松生成使得通过多个单电子转移反应从亚磺酸钠形成硫自由基物种成为可能,其中最终实现了酰基自由基 - 硫自由基偶联。这种直接的自由基 - 自由基偶联策略为合成硫酯等重要合成砌块提供了一种温和且可控的光化学方法。

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