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Synthesis and characterization of chiral phosphirane derivatives of [(μ-H)4Ru4(CO)12] and their application in the hydrogenation of an α,β-unsaturated carboxylic acid

Lookup NU author(s): Manuel Abelairas-Edesa, Arne Ficks, Emeritus Professor Bill Clegg, Dr Lee Higham

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Abstract

© 2017 Elsevier B.V. Ruthenium clusters containing the chiral binaphthyl-derived mono-phosphiranes [(S)-([1,1'-binaphthalen]-2-yl)phosphirane] (S)-1a, [(R)-(2'-methoxy-1,1'-binaphthyl-2-yl)phosphirane] (R)-1b, and the diphosphirane [2,2'-di(phosphiran-1-yl)-1,1'-binaphthalene] (S)-1c have been synthesized and characterized. The clusters are [(μ-H)4Ru4(CO)11((S)-1a)] (S)-2, [(μ-H)4Ru4(CO)11((R)-1b)] (R)-3, 1,1-[(μ-H)4Ru4(CO)10((S)-1c)] (S)-4, [(μ-H)4Ru4(CO)11((S)-binaphthyl-P(s)(H)Et)] (S,S p)-5, [(μ-H)4Ru4(CO)11((S)-binaphthyl-P(R)(H)Et)] (S,R p)-6, [(μ-H)4Ru4(CO)11((R)-binaphthyl-P(s)(H)Et)] (R,S p)-7, [(μ-H)4Ru4(CO)11((R)-binaphthyl-P(R)(H)Et)] (R,R p)-8 and the phosphinidene-capped triruthenium cluster [(μ-H)2Ru3(CO)9(PEt)] 9. Clusters 5-8 are formed via hydrogenation and opening of the phosphirane ring in clusters (S)-2 and (R)-3. The phosphirane-substituted clusters were found to be able to catalyze the hydrogenation of trans-2-methyl-2-butenoic acid (tiglic acid), but no enantioselectivity could be detected. The molecular structures of (S)-4, (R,S p)-7 and 9 have been determined and are presented.


Publication metadata

Author(s): Abdel-Magied AF, Majeed MH, Abelairas-Edesa MF, Ficks A, Ashour RM, Rahaman A, Clegg W, Haukka M, Higham LJ, Nordlander E

Publication type: Article

Publication status: Published

Journal: Journal of Organometallic Chemistry

Year: 2017

Volume: 849-850

Pages: 71-79

Print publication date: 01/11/2017

Online publication date: 18/05/2017

Acceptance date: 15/05/2017

ISSN (print): 0022-328X

ISSN (electronic): 1872-8561

Publisher: Elsevier BV

URL: https://doi.org/10.1016/j.jorganchem.2017.05.031

DOI: 10.1016/j.jorganchem.2017.05.031


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