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Issue 18, 2018
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Reactivity enhancement of a diphosphene by reversible N-heterocyclic carbene coordination

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Abstract

Diphosphene TerMesP = PTerMes (1; TerMes = 2,6-Mes2C6H3; Mes = 2,4,6-Me3C6H2) and NHCMe42 (NHCMe4 = 1,3,4,5-tetramethylimidazol-2-ylidene) exist in an equilibrium mixture with the NHCMe4-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 NHCMe4. On this basis, conditions suitable for the catalytic use of NHCMe4 were identified. Similarly, while the hydrogenation of free diphosphene 1 with H3N·BH3 is very slow, 3 reacts instantaneously with H3N·BH3 at room temperature to afford a dihydrodiphosphane.

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

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Supplementary files

Article information


Submitted
22 Jan 2018
Accepted
26 Mar 2018
First published
27 Mar 2018

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2018,9, 4235-4243
Article type
Edge Article

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

D. Dhara, P. Kalita, S. Mondal, R. S. Narayanan, K. R. Mote, V. Huch, M. Zimmer, C. B. Yildiz, D. Scheschkewitz, V. Chandrasekhar and A. Jana, Chem. Sci., 2018, 9, 4235
DOI: 10.1039/C8SC00348C

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    [Original citation] - Published by The Royal Society of Chemistry.

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