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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 NHCMe4 2 (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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Publication details

The article was received on 22 Jan 2018, accepted on 26 Mar 2018 and first published on 27 Mar 2018


Article type: Edge Article
DOI: 10.1039/C8SC00348C
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    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, Advance Article , DOI: 10.1039/C8SC00348C

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