Work

I(III)-Mediated Arene C–H Amination Using (Hetero)Aryl Nucleophiles

Year: 2023

Type: article

Abstract: Herein, we report the metal-free oxidative C–H amination of arenes via a “heterocyclic group transfer” reaction from an I(III) N -HVI reagent. N-Heterocycles serve as oxidatively masked amine nucleophiles, and the resulting N -arylpyridinium salts are inert to further oxidation. The reaction proceeds under mild conditions, and mechanistic studies indicate the intermediacy of an arene radical cation. Derivatizations of the resulting pyridinium salts to diverse aryl amine scaffolds are demonstrated.

Source: Organic Letters

DOI: 10.1021/acs.orglett.3c00809

Authors: Bill J. Motsch, Jasjit Y. Kaur, Sarah E. Wengryniuk

Institution: Temple University

Language: English

Topic: Oxidative Organic Chemistry Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, Division of Chemistry