4.8 Article

Dicumyl Peroxide as a Methylating Reagent in the Ni-Catalyzed Methylation of Ortho C-H Bonds in Aromatic Amides

Journal

ORGANIC LETTERS
Volume 18, Issue 7, Pages 1698-1701

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b00658

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology
  2. JST Strategic Basic Research Programs Advanced Catalytic Transformation Program for Carbon Utilization (ACT-C) from the Japan Science and Technology Agency

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The direct methylation of ortho C-H bonds in aromatic amides with dicumyl peroxide (DCP) using a nickel complex as the catalyst is reported. The reaction shows a high functional group tolerance and is inhibited by radical scavengers. In reactions of meta-substituted aromatic amides, the reaction proceeds in a highly selective manner at the less hindered C-H bonds.

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