4.8 Article

Palladium-Catalyzed Sequential C-H Activation/Amination with Diaziridinone: An Approach to Indoles

Journal

ORGANIC LETTERS
Volume 23, Issue 9, Pages 3646-3651

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01043

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Funding

  1. National Natural Science Foundation of China [21632005]
  2. Changzhou University

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The paper presents an efficient palladium-catalyzed synthesis of indoles from 2-iodostyrenes and di-t-butyldiaziridinone, simultaneously forming two C-N bonds. The reaction likely proceeds through the insertion of Pd to aryl iodide and subsequent vinyl C-H activation to form a pallada(II)cycle intermediate, which is then bisaminated by di-t-butyldiaziridinone to give the final indole product.
Indoles are an important class of molecules. This paper describes an efficient palladium-catalyzed synthesis of indoles from 2-iodostyrenes and di-t-butyldiaziridinone with a simultaneous installation of two C-N bonds. The reaction process likely proceeds through the oxidative insertion of Pd to aryl iodide and subsequent vinyl C-H activation to from a pallada(II)cycle intermediate, which is bisaminated by di-t-butyldiaziridinone to give the indole product.

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