Issue 44, 2011

Selective hydroformylation-hydrogenation tandem reaction of isoprene to 3-methylpentanal

Abstract

The hydroformylation of isoprene catalysed by rhodium phosphine complexes usually yields a broad mixture of the monoaldehydes, the isomeric methylpentenals, as well as the dialdehyde 3-methyl-1,6-hexandial. Under usual reaction conditions the products of a consecutive hydrogenation are only formed as minor by-products. Surprisingly we discovered now a selective auto-tandem reaction consisting of a hydroformylation and a hydrogenation step if a rhodium complex with the chelate ligand bis(diphenylphosphino)ethane is used as catalyst. If branched aromatic solvents like cumene are applied the conversion of isoprene is nearly quantitatively and the yield of the tandem product 3-methylpentanal amounts to 85%.

Graphical abstract: Selective hydroformylation-hydrogenation tandem reaction of isoprene to 3-methylpentanal

Article information

Article type
Paper
Submitted
07 Jul 2011
Accepted
24 Aug 2011
First published
29 Sep 2011

Dalton Trans., 2011,40, 11742-11747

Selective hydroformylation-hydrogenation tandem reaction of isoprene to 3-methylpentanal

A. Behr, S. Reyer and N. Tenhumberg, Dalton Trans., 2011, 40, 11742 DOI: 10.1039/C1DT11292A

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