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Issue 3, 2016
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A step towards hydroformylation under sustainable conditions: platinum-catalysed enantioselective hydroformylation of styrene in gamma-valerolactone

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Abstract

Platinum-catalysed enantioselective hydroformylation of styrene was performed in γ-valerolactone (GVL) as a proposed environmentally benign reaction medium. Optically active bidentate ligands, possessing various types of chirality elements e.g. central (BDPP), axial (BINAP, SEGPHOS, DM-SEGPHOS, DTBM-SEGPHOS) and planar/central (JOSIPHOS) elements, were applied in in situ generated Pt-diphosphine-tin(II)chloride catalyst systems. In general, slightly higher activities and regioselectivities towards a branched aldehyde (2-phenylpropanal) were obtained in toluene as a reference conventional solvent. However, higher chemoselectivities towards aldehydes (up to 98%) in GVL were obtained at lower temperatures. The application of GVL proved to be also advantageous regarding enantioselectivity: although moderate enantioselectivities were obtained in both solvents, in most cases higher ee values were detected in GVL. From the mechanistic point of view, the formation of different catalytic intermediates and/or different kinetics can be envisaged from the different temperature dependences of ee in GVL and toluene. The 31P-NMR characterization of catalyst species in GVL was also provided.

Graphical abstract: A step towards hydroformylation under sustainable conditions: platinum-catalysed enantioselective hydroformylation of styrene in gamma-valerolactone

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Supplementary files

Article information


Submitted
02 Aug 2015
Accepted
08 Sep 2015
First published
08 Sep 2015

This article is Open Access

Green Chem., 2016,18, 842-847
Article type
Paper
Author version available

A step towards hydroformylation under sustainable conditions: platinum-catalysed enantioselective hydroformylation of styrene in gamma-valerolactone

P. Pongrácz, L. Kollár and L. T. Mika, Green Chem., 2016, 18, 842
DOI: 10.1039/C5GC01778E

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