Azide-Free Synthesis of N-Alkyliminophosphoranes from Phosphines and Hydroxylamine Derivatives

Falk, Eric; Franchino, Allegra; Horak, Teresa; Gürtler, Laura; Morandi∗, Bill

Abstract

A broadly applicable and efficient method for the synthesis of N-alkyliminophosphoranes from phosphines that does not use potentially hazardous alkyl azides is reported. Under iron catalysis, a hydroxylamine-derived triflic acid salt oxidizes phosphines to a wide range of iminophosphorane triflic acid salts. Diphosphines afford phosphine-iminophosphoranes that can serve as ligands in transition metal complexes. The developed method can be employed in the synthesis of mixed diiminophosphoranes and in a traceless Staudinger ligation.

Citation

Falk, E., Franchino, A., Horak, T., Gürtler, L., & Morandi∗, B. (2023). Azide-Free Synthesis of N-Alkyliminophosphoranes from Phosphines and Hydroxylamine Derivatives. Organic Letters, 25(10), 1695-1700. https://doi.org/10.1021/acs.orglett.3c00366

• Journal Article Type: Article
• Acceptance Date: Mar 9, 2023
• Online Publication Date: Mar 9, 2023
• Publication Date: Mar 17, 2023
• Deposit Date: Oct 23, 2023
• Journal: Organic Letters
• Print ISSN: 1523-7060
• Electronic ISSN: 1523-7052
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 25
• Issue: 10
• Pages: 1695-1700
• DOI: https://doi.org/10.1021/acs.orglett.3c00366
• Public URL: https://durham-repository.worktribe.com/output/1814586