Solvent-Free Mechanoradical-Mediated Minisci-Type C–H Alkylation of N‑Heteroarenes

An environmentally friendly new C–H alkylation method of N-heteroarenes facilitated by mechanochemistry is described. Under solvent-free ball-milling, mechanoradicals (SO4 •–) were generated from persulfate via in situ homolysis in the solid state, at as low as −50 °C. These highly oxidizing radical...

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Bibliographic Details
Published in:Organic letters 2023-10, Vol.25 (40), p.7287-7292
Main Authors: Gu, Xiang, Wang, Taoyong, Yan, KaKing
Format: Article
Language:English
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Summary:An environmentally friendly new C–H alkylation method of N-heteroarenes facilitated by mechanochemistry is described. Under solvent-free ball-milling, mechanoradicals (SO4 •–) were generated from persulfate via in situ homolysis in the solid state, at as low as −50 °C. These highly oxidizing radicals readily transform alkyl trifluoroborate salts to their corresponding carbon-based radicals for subsequent C–C bond formation with N-heterocycles. Mechanistic studies unambiguously confirmed the involvement of both oxygen- and alkyl-radical-based intermediates.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c02480