Communication

Manganese-Catalyzed Direct Oxidation of Methyl Ethers to Ketones

  1. Shin Kamijo Dr.,
  2. Yuuki Amaoka,
  3. Masayuki Inoue Prof. Dr.

Article first published online: 10 NOV 2009

DOI: 10.1002/asia.200900420

Issue

Chemistry – An Asian Journal

Chemistry – An Asian Journal

Special Issue: In dedication to the 150th anniversary of Japan–UK diplomatic relations

Volume 5, Issue 3, pages 486–489, March 1, 2010

Additional Information

How to Cite

Kamijo, S., Amaoka, Y. and Inoue, M. (2010), Manganese-Catalyzed Direct Oxidation of Methyl Ethers to Ketones. Chemistry – An Asian Journal, 5: 486–489. doi: 10.1002/asia.200900420

Author Information

  1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 3-5841-0568

Publication History

  1. Issue published online: 22 FEB 2010
  2. Article first published online: 10 NOV 2009
  3. Manuscript Received: 4 SEP 2009

Funded by

  • Grant-in-Aids for Young Scientists
  • Uehara Memorial Foundation
  • TORAY Science Foundation

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Keywords:

  • C[BOND]H activation;
  • ketones;
  • manganese;
  • methyl ethers;
  • oxidation

Graphical Abstract

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Take Me away! Direct C[BOND]H oxidation of alkyl ethers into ketones was achieved using 0.1 mol % of MnCl2 and 4,4′,4′′-tri(tert-butyl)-2,2′:6′,2′′-terpyridine (tBu-terpy) in the presence of mCPBA. Conversion of methyl ethers into ketones was particularly efficient and chemoselective. Electron-deficient oxygen functionalities survived under the reaction conditions. The present method broadens the utility of methyl ethers as stable protective groups for hydroxy functionalities and as precursors to carbonyl compounds.

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