4.8 Article

Heterocycle Synthesis via Direct C-H/N-H Coupling

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 1, Pages 7-10

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ja210959p

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Funding

  1. Welch Foundation [E-1571]
  2. National Institute of General Medical Sciences [R01GM077635]
  3. A. P. Sloan Foundation
  4. Camille and Henry Dreyfus Foundation

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A method for five- and six-membered heterocycle formation by palladium-catalyzed C-H/N-H coupling is presented. The method employs a picolinamide directing group, PhI(OAc)(2) oxidant, and toluene solvent at 80-120 degrees C. Cyclization is effective for sp(2) as well as aliphatic and benzylic sp(3) C-H bonds.

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