Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 15, Pages 6913-6919Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c01630
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Funding
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft (Leibniz Award)
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A general and simple strategy for the site-selective thiolation of various pharmaceutically relevant electron-rich heteroarenes with thiols is reported. This mild and reliable photocatalytic protocol enables C-S coupling at the most electron-rich position of the (multi)halogenated substrates, complementing established methodologies. Experimental and computational studies suggest a radical chain mechanism with the key step being a homolytic aromatic substitution of the heteroaryl halide by an electrophilic thiyl radical, highlighting an underdeveloped reactivity mode.
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