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Synthesis, Characterization and Catalytic Activity Studies of Rhenium Carbonyl Complexes Containing Chiral Diphosphines of the Josiphos and Walphos Families

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Abstract

Ten rhenium carbonyl complexes—[Re(H)(CO)3(1a)], [Re3(µ-H)3(CO)10(1a)], [Re2(CO)9(2a)], [Re2(CO)8(2a)], [Re2(CO)9(2b)], [{Re2(CO)9}2(2b)], [Re2(CO)8(2b)], [Re2(CO)8(1b)], [Re2(µ-H)2(CO)6(2b)] and [Re3(µ-H)3(CO)11(2b)]—containing different bidentate chiral phosphine ligands of the Josiphos (1a, 1b) and Walphos (2a, 2b) families have been synthesized and fully characterized (1a: (R)-1-{(S P)-2-[Bis[3,5-bis(trifluoromethyl)phenyl]phosphino]ferrocenyl}ethyldi(3,5-xylyl)phosphine, 1b: (R)-1-{(S P)-2-[Di(2-furyl)phosphino]ferrocenyl}ethyldi-tert-butylphosphine, 2a: (R)-1-{(R P)-2-[2-[Bis(4-methoxy-3,5-dimethylphenyl)phosphino]phenyl]ferrocenyl}ethylbis[3,5-bis(trifluoromethyl)phenyl]phosphine and 2b: (R)-1-{(R P)-2-[2-(Diphenylphosphino)phenyl]ferrocenyl}ethyldicyclohexylphosphine). The phosphine-substituted clusters were tested for hydrogenation of tiglic acid [trans-2-methyl-2-butenoic acid]. The catalytic reactions gave reasonable conversion rates (15–88 %) under relatively mild conditions but relatively moderate enantiomeric excesses (8–57 %) were observed. The crystal structures of [ReH(CO)3(1a)], [Re2(CO)9(2a)], [{Re2(CO)9}2(2b)] and [Re2(µ-H)2(CO)6(2b)] are presented.

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Acknowledgments

AFA thanks the EU Erasmus Mundus program, FFEEBB1 office, for a scholarship. AKS thanks the Carl Trygger Foundation for a postdoctoral fellowship. MM acknowledges the University of Bologna for financial support.

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Authors and Affiliations

  1. Inorganic Chemistry Research Group, Chemical Physics, Center for Chemistry and Chemical Engineering, Lund University, Box 124, 221 00, Lund, Sweden

    Ahmed F. Abdel-Magied, Manjula S. Patil, Amrendra K. Singh & Ebbe Nordlander

  2. Department of Chemistry, University of Jyväskylä, Box 35, 40014, Jyväskylä, Finland

    Matti Haukka

  3. Dipartimento di Chimica ‘G. Ciamician’, Universitá degli Studi di Bologna, Via Selmi 2, 40126, Bologna, Italy

    Magda Monari

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  1. Ahmed F. Abdel-Magied
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Correspondence to Ebbe Nordlander.

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10876_2014_809_MOESM1_ESM.doc

Supplementary material 1 (DOC 223 kb). Additional supporting information may be found in the online version of this article at the publisher’s website. CCDC 1030320-1030323 contain the supplementary crystallographic data for 3, 5, 8 and 11, respectively. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif

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Abdel-Magied, A.F., Patil, M.S., Singh, A.K. et al. Synthesis, Characterization and Catalytic Activity Studies of Rhenium Carbonyl Complexes Containing Chiral Diphosphines of the Josiphos and Walphos Families. J Clust Sci 26, 1231–1252 (2015). https://doi.org/10.1007/s10876-014-0809-y

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