Aldehyde decarbonylation catalysis under mild conditions

  • Beck C
  • Rathmill S
  • Park Y
 et al. 
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Abstract

Reaction of [RhCl(NBD)]2 with 2.0 equiv of triphos (triphos = bis(2-diphenylphosphinoethyl)phenylphosphine; NBD = bicyclo[2.2.1]hepta-2,5-diene) in THF soln. at room temp. affords [Rh(NBD)(triphos)][Cl] (4a), which was isolated as [Rh(NBD)(triphos)][SbF6] (4b) in 67% yield. Treatment of 4b with aq. formaldehyde in THF soln. at 80° forms [Rh(CO)(triphos)][SbF6] (2a), which reversibly binds a 2nd equiv. of CO(g) to give [Rh(CO)2(triphos)][SbF6] (2b). [Rh(CO)(triphos)][SbF6] is an effective aldehyde decarbonylation catalyst for primary and aryl aldehydes at temps. as low as that of refluxing dioxane, with little or no undesirable side products resulting from β elimination or radical rearrangement. The crystal and mol. structures of [Rh(NBD)(triphos)][BPh4] were detd. by x-ray crystallog. [on SciFinder(R)]

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Authors

  • Christopher M. Beck

  • Scott E. Rathmill

  • You Jung Park

  • Junyi Chen

  • Robert H. Crabtree

  • Louise M. Liable-Sands

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