General Electron-Donor-Acceptor Complex Mediated Thioesterification Reaction via Site-Selective C-H Functionalization using Aryl Sulfonium Salts

04 July 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Comtemporary methods for synthesizing thioesters often necessitate expensive catalysts, and harsh conditions, making their synthesis from chemical feedstocks challenging. Herein, we report a concise metal-, photocatalyst-, and oxidant-free electron donar-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.

Keywords

Thioesterification
site-selective C-H functionalization
electron donor-acceptor (EDA) complex
aryl sulfonium salt

Supplementary materials

Title
Description
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Title
General Electron-Donor-Acceptor Complex Mediated Thioesterification Reaction via site selective C-H Functionalization using Aryl Sulfonium Salts
Description
Experimental details, characterization data and NMR spectra.
Actions

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