Aldehyde decarbonylation catalysis under mild conditions

Citation
Cm. Beck et al., Aldehyde decarbonylation catalysis under mild conditions, ORGANOMETAL, 18(25), 1999, pp. 5311-5317
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANOMETALLICS
ISSN journal
02767333 → ACNP
Volume
18
Issue
25
Year of publication
1999
Pages
5311 - 5317
Database
ISI
SICI code
0276-7333(199912)18:25<5311:ADCUMC>2.0.ZU;2-#
Abstract
Reaction of [RhCl(NBD)](2) with 2.0 equiv of triphos (triphos = bis(2-diphe nylphosphinoethyl)phenylphosphine; NBD = bicyclo[2.2.1]hepta-2,5-diene) in THF solution at room temperature affords [Rh(NBD)(triphos)][Cl] (4a), which was isolated as [Rh(NBD)(triphos)][SbF6] (4b) in 67% yield. Treatment of 4 b with aqueous formaldehyde in THF solution; at 80 degrees C forms [Rh(CO)( triphos)][SbF6] (2a), which reversibly binds a second equivalent of CO(g) t o give [Rh(CO)(2)(triphos)][SbF6] (2b). The complex [Rh(CO)(triphos)][SbF6] has been found to be an effective aldehyde decarbonylation catalyst for pr imary and aryl aldehydes at temperatures as low as that of refluxing dioxan e, with little or no undesirable side products resulting from beta eliminat ion or radical rearrangement.