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Copper-Catalyzed Electrophilic Ortho C(sp²)–H Amination of Aryl Amines: Dramatic Reactivity of Bicyclic System

Author:
Begam, Hasina Mamataj, Choudhury, Rajarshee, Behera, Ashok, Jana, Ranjan
Source:
Organic letters 2019 v.21 no.12 pp. 4651-4656
ISSN:
1523-7052
Subject:
Lewis acids, additives, amination, amines, chemical structure, heterocyclic amines, oxidants
Abstract:
A practical copper-catalyzed, 2-picolinamide-directed ortho C–H amination of anilines with benzoyl-protected hydroxylamines has been disclosed that proceeds smoothly without any external stoichiometric oxidant or additives. Remarkably, besides anilines, bicyclic naphthyl or heterocyclic amines furnished amination products with five- and six-membered cyclic and acyclic amines at the ortho position selectively. This electrophilic C–H amination also proceeds smoothly in water under slightly modified reaction conditions.
Agid:
6478193