Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 11, Pages 2977-2985Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00155a
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Funding
- National Natural Science Foundation of China [21971182, 21771131]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
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The activation of stronger C(non-acyl)-S bond of thioesters for metal- and photoredox catalyst-free visible-light-mediated pyridylthioesterification of styrenes has been reported, showing excellent chemo- and regio-selectivity. This protocol is atom-economical, tolerant to various functional groups, and can be used for gram-scale reactions.
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.
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