4.8 Article

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

Journal

ORGANIC LETTERS
Volume 21, Issue 10, Pages 3774-3779

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01218

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Funding

  1. National Research Foundation of Korea (NRF) - Korean government (MSICT) [NRF-2015R1A5A1008958, NRF-2018R1D1A1B07049189]

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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.

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