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

*Corresponding author for this work

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