Sterically Congested 2, 6‐Disubstituted Anilines from Direct C−N Bond Formation at an Iodine(III) Center. Issue 42 (6th October 2016)

• Record Type: Journal Article
• Authors: Lucchetti, Nicola; Scalone, Michelangelo; Fantasia, Serena; Muñiz, Kilian
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 42(2016)
• Page Start: 13335
• Page End: 13339
• Publication Date: 2016-10-06
• Subjects: amination -- anilines -- arylation -- hypervalent iodine -- phthalimide; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201606599
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 2, 6‐Disubstituted anilines are readily prepared from the direct reaction between amides and diaryliodonium salts. As demonstrated for 24 different examples, the reaction is of unusually broad scope with respect to the sterically congested arene and the nitrogen source, occurs without the requirement for any additional promoter, and proceeds through a direct reductive elimination at the iodine(III) center. The efficiency of the coupling procedure is further demonstrated within the short synthesis of a chemerin binding inhibitor. Abstract : The bulkier, the better : A metal‐free coupling of diaryliodonium salts with potassium tetrafluorophthalimide and related nitrogen sources enables a general and synthetically productive access to N‐arylated amides with 2, 6‐disubstitution patterns on the arene ring. 2, 6‐Disubstituted anilines—which are important building blocks in pharmaceutically relevant structures—are also accessible.