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

Jing Li, Jinhua Chen, Luying Wang and Yian Shi*

*Department of Chemistry, Colorado State University, Fort Collins 80523, Colorado, United States, Email: shiyiancczu.edu.cn

J. Li, J. Chen, L. Wang, Y. Shi, Org. Lett., 2021, 23, 3626-3630.

DOI: 10.1021/acs.orglett.1c01043 (free Supporting Information)


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Abstract

An efficient palladium-catalyzed reaction of 2-iodostyrenes with di-t-butyldiaziridinone provides indoles via a simultaneous installation of two C-N bonds. The reaction likely proceeds through an 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.

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proposed mechanism



Key Words

indoles


ID: J54-Y2021