Issue 18, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
20 Wax 2019
Accepted
23 Ado 2019
First published
26 Ado 2019

Org. Chem. Front., 2019,6, 3205-3209

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, 6, 3205 DOI: 10.1039/C9QO00786E

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