Palladium-Catalyzed Csp³–H Bond mono-Aroyloxylation of O-Alkyl Substituted 2,4,6-Trimethoxybenzaldoxime Ethers

Abstract

A palladium-catalyzed Csp³–H bond mono-aroyloxylation of O-alkyl substituted oxime ethers has been developed by using 2,4,6-trimethoxybenzaldoxime as an exo-type directing group with exclusive site-selectivity. With the wide range of masked aliphatic alcohol substrates and aromatic acid coupling partners, the protocol allows rapid access to various 2-alkyl substituted glycol derivatives in synthetically useful to good yields. The employed directing group is readily removed, accordingly affording valuable functionalized aliphatic alcohols. When the solvent from hybrid DCE/HFIP to CH₃CN, non-directed oxidative cross-coupling is observed between the electron-rich aromatic ring of substrates and aromatic acid partners.

Key words

palladium-catalysis - Csp³–H bond functionalization - aroyl­oxylation - masked aliphatic alcohol - oxidative cross-coupling

• References and Notes

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