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Minisci C–H alkylation of N-heteroarenes with aliphatic alcohols via β-scission of alkoxy radical intermediates

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Abstract

A Minisci-type C–H alkylation reaction of N-heteroarenes with aliphatic alcohols via β-scission of alkoxy radical intermediates under photoredox-catalyzed conditions was developed. The use of the benziodoxole acetate (BI-OAc) oxidant is critical to achieving high efficiency under mild conditions using a slight excess of an alcohol reactant. Primary, secondary, and tertiary alcohols all are compatible. Reactions of various complex N-heteroarenes including drug molecules and steroid natural products have been demonstrated.

Graphical abstract: Minisci C–H alkylation of N-heteroarenes with aliphatic alcohols via β-scission of alkoxy radical intermediates

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Publication details

The article was received on 20 Jun 2019, accepted on 23 Jul 2019 and first published on 26 Jul 2019


Article type: Research Article
DOI: 10.1039/C9QO00786E
Org. Chem. Front., 2019, Advance Article

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    Minisci C–H alkylation of N-heteroarenes with aliphatic alcohols via β-scission of alkoxy radical intermediates

    X. Hu, G. Li, G. He and G. Chen, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00786E

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