4.8 Article

Rh(I)-Catalyzed Alkylation of ortho-C-H Bonds in Aromatic Amides with Maleimides

Journal

ORGANIC LETTERS
Volume 19, Issue 17, Pages 4544-4547

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02135

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Funding

  1. JST Strategic Basic Research Program Advanced Catalytic Transformation Program for Carbon Utilization (ACT-C) [JPMJCR12YS]
  2. MEXT [17H06091]

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An alkylation of C-H bonds with maleimides by a rhodium-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety as the directing group is reported. Various N-substituents in the maleimide, including methyl, ethyl, cyclohexyl, benzyl, and phenyl groups and even H, are applicable to the reaction. The reaction is highly regioselective at the less hindered ortho-C-H bond when meta-substituted aromatic amides are used as substrates.

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