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

Eric Falk, Allegra Franchino, Teresa Horak, Laura Gürtler and Bill Morandi*

*Laboratorium für Organische Chemie, ETH Zürich, Vladimir-Prelog-Weg 3, HCI, 8093 Zürich, Switzerland, Email: bill.morandiorg.chem.ethz.ch

E. Falk, A. Franchino, T. Horak, L. Gürtler, B. Morandi, Org. Lett., 2023, 25, 1695-1700.

DOI: 10.1021/acs.orglett.3c00366


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Abstract

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.


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Key Words

iminophosphoranes


ID: J54-Y2023