Reactivity enhancement of a diphosphene by reversible N-heterocyclic carbene coordination

Diphosphene Ter(Mes)P = PTer(Mes) (1; Ter(Mes) = 2,6-Mes(2)C(6)H(3); Mes = 2,4,6-Me(3)C(6)H(2)) and NHC(Me(4))2 (NHC(Me(4)) = 1,3,4,5-tetramethylimidazol-2-ylidene) exist in an equilibrium mixture with the NHC(Me(4))-coordinated diphosphene 3. While uncoordinated 1 is inert to hydrolysis, the NHC ad...

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Autores principales: Dhara, Debabrata, Kalita, Pankaj, Mondal, Subhadip, Narayanan, Ramakirushnan Suriya, Mote, Kaustubh R., Huch, Volker, Zimmer, Michael, Yildiz, Cem B., Scheschkewitz, David, Chandrasekhar, Vadapalli, Jana, Anukul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5944230/
https://www.ncbi.nlm.nih.gov/pubmed/29780553
http://dx.doi.org/10.1039/c8sc00348c
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author Dhara, Debabrata
Kalita, Pankaj
Mondal, Subhadip
Narayanan, Ramakirushnan Suriya
Mote, Kaustubh R.
Huch, Volker
Zimmer, Michael
Yildiz, Cem B.
Scheschkewitz, David
Chandrasekhar, Vadapalli
Jana, Anukul
author_facet Dhara, Debabrata
Kalita, Pankaj
Mondal, Subhadip
Narayanan, Ramakirushnan Suriya
Mote, Kaustubh R.
Huch, Volker
Zimmer, Michael
Yildiz, Cem B.
Scheschkewitz, David
Chandrasekhar, Vadapalli
Jana, Anukul
author_sort Dhara, Debabrata
collection PubMed
description Diphosphene Ter(Mes)P = PTer(Mes) (1; Ter(Mes) = 2,6-Mes(2)C(6)H(3); Mes = 2,4,6-Me(3)C(6)H(2)) and NHC(Me(4))2 (NHC(Me(4)) = 1,3,4,5-tetramethylimidazol-2-ylidene) exist in an equilibrium mixture with the NHC(Me(4))-coordinated diphosphene 3. While uncoordinated 1 is inert to hydrolysis, the NHC adduct 3 readily undergoes hydrolysis to afford a phosphino-substituted phosphine oxide with the liberation of NHC(Me(4)). On this basis, conditions suitable for the catalytic use of NHC(Me(4)) were identified. Similarly, while the hydrogenation of free diphosphene 1 with H(3)N·BH(3) is very slow, 3 reacts instantaneously with H(3)N·BH(3) at room temperature to afford a dihydrodiphosphane.
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spelling pubmed-59442302018-05-18 Reactivity enhancement of a diphosphene by reversible N-heterocyclic carbene coordination Dhara, Debabrata Kalita, Pankaj Mondal, Subhadip Narayanan, Ramakirushnan Suriya Mote, Kaustubh R. Huch, Volker Zimmer, Michael Yildiz, Cem B. Scheschkewitz, David Chandrasekhar, Vadapalli Jana, Anukul Chem Sci Chemistry Diphosphene Ter(Mes)P = PTer(Mes) (1; Ter(Mes) = 2,6-Mes(2)C(6)H(3); Mes = 2,4,6-Me(3)C(6)H(2)) and NHC(Me(4))2 (NHC(Me(4)) = 1,3,4,5-tetramethylimidazol-2-ylidene) exist in an equilibrium mixture with the NHC(Me(4))-coordinated diphosphene 3. While uncoordinated 1 is inert to hydrolysis, the NHC adduct 3 readily undergoes hydrolysis to afford a phosphino-substituted phosphine oxide with the liberation of NHC(Me(4)). On this basis, conditions suitable for the catalytic use of NHC(Me(4)) were identified. Similarly, while the hydrogenation of free diphosphene 1 with H(3)N·BH(3) is very slow, 3 reacts instantaneously with H(3)N·BH(3) at room temperature to afford a dihydrodiphosphane. Royal Society of Chemistry 2018-03-27 /pmc/articles/PMC5944230/ /pubmed/29780553 http://dx.doi.org/10.1039/c8sc00348c Text en This journal is © The Royal Society of Chemistry 2018 https://creativecommons.org/licenses/by-nc/3.0/This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Dhara, Debabrata
Kalita, Pankaj
Mondal, Subhadip
Narayanan, Ramakirushnan Suriya
Mote, Kaustubh R.
Huch, Volker
Zimmer, Michael
Yildiz, Cem B.
Scheschkewitz, David
Chandrasekhar, Vadapalli
Jana, Anukul
Reactivity enhancement of a diphosphene by reversible N-heterocyclic carbene coordination
title Reactivity enhancement of a diphosphene by reversible N-heterocyclic carbene coordination
title_full Reactivity enhancement of a diphosphene by reversible N-heterocyclic carbene coordination
title_fullStr Reactivity enhancement of a diphosphene by reversible N-heterocyclic carbene coordination
title_full_unstemmed Reactivity enhancement of a diphosphene by reversible N-heterocyclic carbene coordination
title_short Reactivity enhancement of a diphosphene by reversible N-heterocyclic carbene coordination
title_sort reactivity enhancement of a diphosphene by reversible n-heterocyclic carbene coordination
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5944230/
https://www.ncbi.nlm.nih.gov/pubmed/29780553
http://dx.doi.org/10.1039/c8sc00348c
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