This work was generously supported by the NIGMS CMLD initiative (P50 GM067041). We thank Professors Scott Schaus (Boston University) and Jinquan Yu (Brandeis University) for helpful discussions, Dr. Paul Ralifo (Boston University) for assistance with NMR structure elucidation, CEM Corporation (Matthews, NC) for assistance with microwave instrumentation, and Symyx Technologies, Inc. (Santa Clara, CA) for assistance with chemical reaction planning software.
Nucleophilic Addition to N-Phosphinylimines by Rare-Earth-Metal Triflate/Trifluoroacetic Anhydride Activation†
Article first published online: 23 AUG 2007
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 46, Issue 39, pages 7470–7472, October 1, 2007
How to Cite
Ong, Winnie W., Beeler, Aaron B., Kesavan, S., Panek, James S. and Porco, John A. (2007), Nucleophilic Addition to N-Phosphinylimines by Rare-Earth-Metal Triflate/Trifluoroacetic Anhydride Activation. Angew. Chem. Int. Ed., 46: 7470–7472. doi: 10.1002/anie.200700694
- Issue published online: 20 SEP 2007
- Article first published online: 23 AUG 2007
- Manuscript Received: 14 FEB 2007
- NIGMS CMLD initiative. Grant Number: P50 GM067041
- synthetic methods
Hydrated lanthanum triflate has been shown to be an effective and highly active Lewis acid catalyst for nucleophilic addition to N-phosphinylimines in the presence of trifluoroacetic anhydride (TFAA; see scheme). Unexpectedly, trifluoroacetamide products are produced in a novel process which likely involves consecutive acylation/hydration of N-phosphinylimine substrates and subsequent nucleophilic addition.