Iminophosphanes: Synthesis, Rhodium Complexes, and Ruthenium(II)-Catalyzed Hydration of Nitriles

Mark K. Rong, Koen Van Duin, Tom Van Dijk, Jeroen J.M. De Pater, Berth Jan Deelman, Martin Nieger, A. W. Ehlers, J. Chris Slootweg, Koop Lammertsma

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

Highly stable iminophosphanes, obtained from alkylating nitriles and reaction of the resulting nitrilium ions with secondary phosphanes, were explored as tunable P-monodentate and 1,3-P,N bidentate ligands in rhodium complexes. X-ray crystal structures are reported for both κ1 and κ2 complexes with the counterion in one of them being an unusual anionic coordination polymer of silver triflate. The iminophosphane-based ruthenium(II)-catalyzed hydration of benzonitrile in 1,2-dimethoxyethane (180 °C, 3 h) and water (100 °C, 24 h) and under solvent free conditions (180 °C, 3 h) results in all cases in the selective formation of benzamide with yields of up to 96%, thereby outperforming by far the reactions in which the common 2-pyridyldiphenylphosphane is used as the 1,3-P,N ligand.

Original languageEnglish
Pages (from-to)1079-1090
Number of pages12
JournalOrganometallics
Volume36
Issue number5
DOIs
Publication statusPublished - 13 Mar 2017

Cite this

Rong, M. K., Van Duin, K., Van Dijk, T., De Pater, J. J. M., Deelman, B. J., Nieger, M., ... Lammertsma, K. (2017). Iminophosphanes: Synthesis, Rhodium Complexes, and Ruthenium(II)-Catalyzed Hydration of Nitriles. Organometallics, 36(5), 1079-1090. https://doi.org/10.1021/acs.organomet.7b00057