Metal-free photocleavage of the C(non-acyl)–S bond of thioesters for regioselective pyridylthioesterification of styrenes

Transformation of thioesters via transition-metal-mediated C(acyl)–S bond cleavage is an emerging method to forge C–C and C–S bonds. Herein, we report the first activation of a stronger C(non-acyl)–S bond of thioesters for metal- and photoredox catalyst-free visible-light-mediated pyridylthioesterif...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-05, Vol.9 (11), p.2977-2985
Main Authors: Wu, Qi, You-Hui, Zhao, Lu-Lu, Chai, Hai-Yan, Li, Hong-Xi, Li
Format: Article
Language:English
Subjects:
Atom economy
Bonding strength
Catalysts
Ductile-brittle transition
Functional groups
Irradiation
Light irradiation
Organic chemistry
Photoredox catalysis
Radiation
Selectivity
Styrenes
Substrates
Thioesters
Transition metals
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Summary:Transformation of thioesters via transition-metal-mediated C(acyl)–S bond cleavage is an emerging method to forge C–C and C–S bonds. Herein, we report the first activation of a stronger C(non-acyl)–S bond of thioesters for metal- and photoredox catalyst-free visible-light-mediated pyridylthioesterification of styrenes with excellent chemo- and regio-selectivity. This atom-economic protocol exhibits high functional group tolerance, is applicable to follow-up transformation of drug molecules, and is easy to set up for gram-scale reaction. Mechanistic studies revealed that this process is initiated by blue light irradiation of ternary electron donor–acceptor (EDA) complexes, formed by the aggregation of two substrates with HNEt2 as a traceless electron-donor.
ISSN:2052-4110
2052-4110
DOI:10.1039/d2qo00155a