Manganese dioxide-methanesulfonic acid promoted direct dehydrogenative alkylation of sp3 C-H bonds adjacent to a heteroatom

J Org Chem. 2013 Apr 5;78(7):3104-12. doi: 10.1021/jo4000674. Epub 2013 Mar 26.

Abstract

A manganese dioxide (MnO2)-methanesulfonic acid (CH3SO3H) oxidation system has been developed to efficiently promote direct coupling of benzylic ethers and carbamates with simple ketones via oxidative C-H bond activation. The alkylation proceeds smoothly under air atmosphere to afford the corresponding products in good to excellent yields (53-87%). The employment of the combination of MnO2 and CH3SO3H is attractive on the basis of economical and environmental issues.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkylation
  • Hydrogenation
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Manganese Compounds / chemistry*
  • Mesylates / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Oxides / chemistry*

Substances

  • Ketones
  • Manganese Compounds
  • Mesylates
  • Oxides
  • methanesulfonic acid
  • manganese dioxide