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

Fingerprint

Nitriles
Rhodium
phosphine
Ruthenium
nitriles
rhodium
Hydration
ruthenium
hydration
Ligands
ligands
synthesis
coordination polymers
Polymers
Crystal structure
silver
Ions
X rays
crystal structure
Water

Cite this

Rong, Mark K. ; Van Duin, Koen ; Van Dijk, Tom ; De Pater, Jeroen J.M. ; Deelman, Berth Jan ; Nieger, Martin ; Ehlers, A. W. ; Slootweg, J. Chris ; Lammertsma, Koop. / Iminophosphanes : Synthesis, Rhodium Complexes, and Ruthenium(II)-Catalyzed Hydration of Nitriles. In: Organometallics. 2017 ; Vol. 36, No. 5. pp. 1079-1090.
@article{04e6f26317114f87a7ada077e517717c,
title = "Iminophosphanes: Synthesis, Rhodium Complexes, and Ruthenium(II)-Catalyzed Hydration of Nitriles",
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.",
author = "Rong, {Mark K.} and {Van Duin}, Koen and {Van Dijk}, Tom and {De Pater}, {Jeroen J.M.} and Deelman, {Berth Jan} and Martin Nieger and Ehlers, {A. W.} and Slootweg, {J. Chris} and Koop Lammertsma",
year = "2017",
month = "3",
day = "13",
doi = "10.1021/acs.organomet.7b00057",
language = "English",
volume = "36",
pages = "1079--1090",
journal = "Organometallics",
issn = "1520-6041",
publisher = "American Chemical Society",
number = "5",

}

Iminophosphanes : Synthesis, Rhodium Complexes, and Ruthenium(II)-Catalyzed Hydration of Nitriles. / Rong, Mark K.; Van Duin, Koen; Van Dijk, Tom; De Pater, Jeroen J.M.; Deelman, Berth Jan; Nieger, Martin; Ehlers, A. W.; Slootweg, J. Chris; Lammertsma, Koop.

In: Organometallics, Vol. 36, No. 5, 13.03.2017, p. 1079-1090.

Research output: Contribution to JournalArticleAcademicpeer-review

TY - JOUR

T1 - Iminophosphanes

T2 - Synthesis, Rhodium Complexes, and Ruthenium(II)-Catalyzed Hydration of Nitriles

AU - Rong, Mark K.

AU - Van Duin, Koen

AU - Van Dijk, Tom

AU - De Pater, Jeroen J.M.

AU - Deelman, Berth Jan

AU - Nieger, Martin

AU - Ehlers, A. W.

AU - Slootweg, J. Chris

AU - Lammertsma, Koop

PY - 2017/3/13

Y1 - 2017/3/13

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85017519923&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85017519923&partnerID=8YFLogxK

U2 - 10.1021/acs.organomet.7b00057

DO - 10.1021/acs.organomet.7b00057

M3 - Article

VL - 36

SP - 1079

EP - 1090

JO - Organometallics

JF - Organometallics

SN - 1520-6041

IS - 5

ER -