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

02 February 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

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 an oxidatively masked amine nucleophile and the resulting N-aryl pyridinium salts are inert to further oxidation. The products provide a versatile handle to access valuable aryl amine derivatives. The reaction proceeds under mild conditions and has good scope of both arene and N-heterocycle.

Keywords

C-H amination
radical cation
hypervalent iodine
pyridinium salts
oxidative functionalization

Supplementary materials

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Description
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Supporting Information
Description
Experimental Procedures, Full Characterization for all Novel Compounds, NMR Spectra
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