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

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초록

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.

키워드

ELECTRON-DEFICIENT ALKENES; BOND FORMATION; THIOL ESTERS; C-S; SULFENYLATION; HYDROXYSULFENYLATION; SULFONYLATION; DERIVATIVES; INDOLES; ALKYNES
제목
Visible-Light-Promoted Thiyl Radical Generation from Sodium Sulfinates: A Radical-Radical Coupling to Thioesters
저자
Bogonda, Ganganna; Patil, Dilip V.; Kim, Hun Young; Oh, Kyungsoo
DOI
10.1021/acs.orglett.9b01218
발행일
2019-05
유형
Article
저널명
Organic Letters
권
21
호
10
페이지
3774 ~ 3779