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Chemoselectivity in the rhodium-catalyzed hydroformylation of 4-vinylpyridine: crucial role of phosphine ligand in promoting carbonylation instead of hydrogenation

2000; Elsevier BV; Volume: 599; Issue: 2 Linguagem: Inglês

10.1016/s0022-328x(00)00011-5

ISSN

1872-8561

Autores

Aldo Caiazzo, Roberta Settambolo, Lorenzo Pontorno, Raffaello Lazzaroni,

Tópico(s)

Cyclopropane Reaction Mechanisms

Resumo

Abstract Hydroformylation of 4-vinylpyridine (4VP) in benzene with Rh4(CO)12/PMe2Ph or Rh4CO12 as catalytic precursor shows completely different chemoselectivity, carbonylation product (branched aldehyde) largely prevailing with the first catalyst, hydrogenation product 4-ethylpyridine (4EP) with the second one. Different phosphines and P/Rh ratios were also used, and a comparison with 3-vinylpyridine (3VP) under the same experimental conditions was made too. In all the experiments 3VP exclusively gives aldehidic products. In the case of 4VP, hydrogenation prevails on carbonylation at low P/Rh ratio (

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