Palladium-catalyzed electrochemical C(sp3)–H acetoxylation of alcohol derivatives with an exo-directing group

Daisuke Ogawa; Ayumu Sasaki; Takuya Kochi; Fumitoshi Kakiuchi

doi:10.1039/D4OB01241K

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Palladium-catalyzed electrochemical C(sp³)–H acetoxylation of alcohol derivatives with an exo-directing group†

Daisuke Ogawa,^a Ayumu Sasaki,^a Takuya Kochi

^a and Fumitoshi Kakiuchi

*^ab

Author affiliations

* Corresponding authors

^a Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan
E-mail: kakiuchi@chem.keio.ac.jp

^b JST, CREST, 4-1-8 Honcho, Kawaguchi, Saitama, Japan

Abstract

Palladium-catalyzed electrochemical C(sp³)–H acetoxylation to prepare 1,2-diol derivatives was achieved using oxime ethers as exo-directing groups. Various substrates containing alkoxy groups with a methyl branch at the α-position as well as norbornan-2-ol derivative were acetoxylated only using a catalytic amount of Pd(OAc)₂ along with NaOAc/Ac₂O/AcOH under anodic oxidation conditions.

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Article information

DOI: https://doi.org/10.1039/D4OB01241K
Article type: Paper
Submitted: 27 Jul 2024
Accepted: 27 Aug 2024
First published: 02 Sep 2024
This article is Open Access

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Org. Biomol. Chem., 2024,22, 7696-7701

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Palladium-catalyzed electrochemical C(sp³)–H acetoxylation of alcohol derivatives with an exo-directing group

D. Ogawa, A. Sasaki, T. Kochi and F. Kakiuchi, Org. Biomol. Chem., 2024, 22, 7696 DOI: 10.1039/D4OB01241K

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Organic & Biomolecular Chemistry