These authors contributed equally to this work.
Phosphine-Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides†
Article first published online: 25 OCT 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 48, pages 12036–12040, November 26, 2012
How to Cite
Kosal, A. D., Wilson, E. E. and Ashfeld, B. L. (2012), Phosphine-Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides . Angew. Chem. Int. Ed., 51: 12036–12040. doi: 10.1002/anie.201206533
We thank Prof. Xavier Creary for helpful discussions. Financial support for this work was received from the NSF (CHE-1056242) and the University of Notre Dame.
- Issue published online: 21 NOV 2012
- Article first published online: 25 OCT 2012
- Manuscript Received: 14 AUG 2012
- NSF. Grant Number: CHE-1056242
- University of Notre Dame
- carboxylic acids;
- homogeneous catalysis;
- Staudinger ligation
Redox catalysis: Aryl amides, imides, lactams, and dipeptides are obtained through a direct Staudinger ligation mediated by phosphine-based redox catalysis (see scheme). Mechanistic studies indicate the involvement of a phosphonium carboxylate intermediate that leads to a 1,3-acyl migration and thus results in CN bond formation.