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General electron–donor–acceptor complex mediated thioesterification reaction via site-selective C–H functionalization using aryl sulfonium Salts.
- 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]
- Subjects :
- POTASSIUM salts
CHEMICAL synthesis
VISIBLE spectra
THIOESTERS
AROMATIC compounds
Subjects
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