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Hydroformylation of unsaturated esters and 2,3-dihydrofuran under solventless conditions at room temperature catalysed by rhodium N-pyrrolylphosphine catalysts

Abstract

Rhodium complexes of the type HRh(CO)L3 (where L is an N-pyrrolyl phosphine, such as P(NC4H4)3, PPh(NC4H4)2, or PPh2(NC4H4)) were applied in the hydroformylation of less reactive unsaturated substrates, namely allyl acetate, butyl acrylate, methyl acrylate, 2,3-dihydrofuran and vinyl acetate. Even at room temperature, these catalysts enabled complete substrate conversion and high chemoselectivity towards the corresponding aldehydes. High conversion of vinyl acetate (88% in 6h) to the branched aldehyde was obtained with HRh(CO)[P(NC4H4)3]3 at 25 °C. An increase of turnover frequency, TOF, up to 2000 mol mol-1 h-1 was achieved in this reaction under 20 bar of the syngas (H2/CO = 1) at 80 °C. The introduction of chiral phosphines, BINAP or Ph-BPE, to this system resulted in the production of a branched aldehyde with enantioselectivity, ee, up to 44 and 81%, respectively. High activity combined with high enantioselectivity was achieved due to the formation of the mixed rhodium hydrides, HRh(CO)[P(NC4H4)3](BINAP) and HRh(CO)[P(NC4H4)3](Ph-BPE), identified by NMR, method.

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Publication details

The article was received on 27 Aug 2019, accepted on 05 Oct 2019 and first published on 07 Oct 2019


Article type: Paper
DOI: 10.1039/C9NJ04438H
New J. Chem., 2019, Accepted Manuscript

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    Hydroformylation of unsaturated esters and 2,3-dihydrofuran under solventless conditions at room temperature catalysed by rhodium N-pyrrolylphosphine catalysts

    W. Alsalahi and A. M. Trzeciak, New J. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9NJ04438H

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