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General electron–donor–acceptor complex mediated thioesterification reaction via site-selective C–H functionalization using aryl sulfonium Salts.

Authors :
Patel, Roshan I.
Saxena, Barakha
Sharma, Anuj
Source :
Green Chemistry; 10/7/2024, Vol. 26 Issue 19, p10265-10274, 10p
Publication Year :
2024

Abstract

Contemporary methods for synthesizing thioesters often necessitate expensive catalysts and harsh conditions, making their synthesis from chemical feedstocks challenging. Herein, we report a sustainable metal-, photocatalyst-, and oxidant-free electron donor–acceptor (EDA) mediated synthesis of thioesters via site-selective C–H functionalization using aryl sulfonium salts (acceptor) with potassium thioacid salts (donor) under visible light irradiation. Our approach enables rapid access to thioesters from a wide variety of arenes, including pharmaceutical and agrochemical compounds, as well as a diverse range of alkyl, aryl, and heteroaryl potassium thioacid salts with excellent efficiency and regioselectivity. Mechanistic studies supported the formation of an EDA-complex, and radical trapping experiments corroborated the involvement of a radical-based mechanism for the product formation. Moreover, our method demonstrates excellent atom economy and E-factor scores, which are considered excellent in terms of safety, economic and ecological yardsticks. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
14639262
Volume :
26
Issue :
19
Database :
Complementary Index
Journal :
Green Chemistry
Publication Type :
Academic Journal
Accession number :
179994850
Full Text :
https://doi.org/10.1039/d4gc03768e