Chiral (Diphosphonite)platinum complexes in asymmetric hydroformylation

R. Duren, van, L.L.J.M. Cornelissen, J.I. Vlugt, van der, J.P.J. Huijbers, A.M. Mills, A.L. Spek, C. Müller, D. Vogt

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Abstract

The chiral diphosphonite ligand (11bR,11bR)-4,4-(9,9-dimethyl-9H-xanthene-4,5-diyl)bis[dinaphtho[2,1-d:1,2-f][1,3,2]dioxaphosphepin] ((R,R)-XantBino; (R)-1), based on a rigid xanthene backbone, was applied in the Pt/Sn-catalyzed hydroformylation of styrene (4a), 4-methylstyrene (4b), vinyl acetate (4c), and allyl acetate (4d), by using a Pt/Sn ratio of 1 : 1. High ee of up to 80% were observed, along with good regioselectivities towards the desired branched aldehydes. For styrene, an interesting inversion in the stereoselection process was observed at elevated temperatures, and a mechanism is proposed considering the temperature dependence of the regioselectivity. The complex [PtCl2{(S,S)-XantBino}] ((S)-2) was characterized by X-ray crystal-structure analysis, revealing an unusual out-of-plane ligand coordination of the metal fragment. The complex [PtCl(SnCl3){(R,R)-XantBino}] ((R)-3) was characterized by means of 31P-NMR spectroscopy.
Original languageEnglish
Pages (from-to)1547-1558
JournalHelvetica Chimica Acta
Volume89
Issue number8
DOIs
Publication statusPublished - 2006

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    Duren, van, R., Cornelissen, L. L. J. M., Vlugt, van der, J. I., Huijbers, J. P. J., Mills, A. M., Spek, A. L., Müller, C., & Vogt, D. (2006). Chiral (Diphosphonite)platinum complexes in asymmetric hydroformylation. Helvetica Chimica Acta, 89(8), 1547-1558. https://doi.org/10.1002/hlca.200690156