Hydroxamic Acids as Chemoselective (ortho-Amino)arylation Reagents via Sigmatropic Rearrangement

Saad Shaaban; Veronica Tona; Bo Peng; Nuno Maulide

doi:10.1002/anie.201703667

Hydroxamic Acids as Chemoselective (ortho-Amino)arylation Reagents via Sigmatropic Rearrangement

Angew Chem Int Ed Engl. 2017 Aug 28;56(36):10938-10941. doi: 10.1002/anie.201703667. Epub 2017 Aug 2.

Authors

Saad Shaaban¹, Veronica Tona¹, Bo Peng², Nuno Maulide¹

Affiliations

¹ Institute of Organic Chemistry, University of Vienna, Währinger Strasse 38, 1090, Wien, Austria.
² Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua, 321004, China.

PMID: 28691189
DOI: 10.1002/anie.201703667

Abstract

The use of readily available hydroxamic acids as reagents for the chemoselective (ortho-amino)arylation of amides is described. This reaction proceeds under metal-free, mild conditions, displays a very broad scope, and constitutes a direct approach for the metal-free attachment of aniline residues to carbonyl derivatives.

Keywords: amides; aminoarylation; chemoselectivity; hydroxamic acids; sigmatropic rearrangement.

Publication types

Research Support, Non-U.S. Gov't