pi-Bond Directed C-2 Amination of Indoles: Catalysis Development, Mechanistic Investigation, and Substrate Scope

14 October 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Cooperative functionalization of N-heterocycles, common motifs present in pharmaceuticals, agrochemicals, functional mate-rials, and natural products, is attractive but a challenging task. In this work, we report a bond directed C2-H functionaliza-tion/amination of indoles with N-heteroarenes in the presence of NiCl2, alternative to Pd-catalysis. Mechanistic studies did not support an oxidative dearomatization, norbornene type C–H functionalization, or allylic C–H activation as likely path-ways and suggest the involvement of Friedel-Crafts type pi-bond directed C–H bond activation as the likely pathway. The methodology is operationally simple, scalable, high yielding and offers a broad scope with high functional group tolerance.

Keywords

Catalysis
Nickel
Palladium
C-H Activation
Heterocycles
amination
Sustainable

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