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Paper | Special issue | Vol 101, No. 1, 2020, pp.223-234
Published online, 5th August, 2019
DOI: 10.3987/COM-19-S(F)16
Pyridine-Directed Rh-Catalyzed C6-Selective C–H Acetoxylation of 2-Pyridones

Sunit Hazra, Koji Hirano,* and Masahiro Miura*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

Abstract

A Rh(III)-catalyzed C-H acetoxylation of 2-pyridones with phenyliodine(III) diacetate (PIDA) in a DCE/AcOH mixed solvent system has been developed using N-2-pyridyl function as directing group. The reaction occurs under mild conditions, typically in air at 40 oC, to selectively produce the corresponding C6-acetoxylated 2-pyridones in moderate to good yields.