Synthesis of Complex Diarylamines through a Ring‐Opening Difunctionalization Strategy**

Author:

Linde Erika1ORCID,Olofsson Berit1ORCID

Affiliation:

1. Department of Organic Chemistry Arrhenius Laboratory Stockholm University 106 91 Stockholm Sweden

Abstract

AbstractThe diarylation and skeletal diversification of unstrained cyclic amines was exploited to expand and modify the favorable properties of this important substrate class with pivotal roles in drug discovery. Cyclic amines were employed in the synthesis of a novel class of amino‐substituted diaryliodonium salts, which were converted to highly functionalized diarylamines through an atom‐efficient one‐pot N‐arylation/ring opening reaction with external nucleophiles. The reaction proceeds through in situ formation of a diarylammonium intermediate that undergoes a nucleophilic ring opening by cleavage of the strong C−N bond. A wide variety of diarylamines was obtained through introduction of two different aryl groups of varied electronics, and the retained iodo‐substituent enables downfield diversifications of the products. More than 20 nucleophiles, including amines, phenols, carboxylic acids, thiols and halides, were alkylated with high functional group tolerance, and the strategy proved efficient also in in late‐stage functionalization of natural products and pharmaceuticals.

Funder

Vetenskapsrådet

Publisher

Wiley

Subject

General Medicine

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