Aldehyde Decarbonylation Catalysis under Mild Conditions

Christopher M. Beck, Scott E. Rathmill, You Jung Park, Junyi Chen, and Robert H. Crabtree*
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06511
Louise M. Liable-Sands and Arnold L. Rheingold*
University of Delaware, Department of Chemistry, Newark, Delaware 19716
Organometallics, 1999, 18 (25), pp 5311–5317
DOI: 10.1021/om9905106
Publication Date (Web): November 17, 1999
Copyright © 1999 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

Abstract Image

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 solution at room temperature affords [Rh(NBD)(triphos)][Cl] (4a), which was isolated as [Rh(NBD)(triphos)][SbF6] (4b) in 67% yield. Treatment of 4b with aqueous formaldehyde in THF solution at 80 °C forms [Rh(CO)(triphos)][SbF6] (2a), which reversibly binds a second equivalent of CO(g) to give [Rh(CO)2(triphos)][SbF6] (2b). The complex [Rh(CO)(triphos)][SbF6] has been found to be an effective aldehyde decarbonylation catalyst for primary and aryl aldehydes at temperatures as low as that of refluxing dioxane, with little or no undesirable side products resulting from β elimination or radical rearrangement.

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History

  • Published In Issue December 06, 1999
  • Received July 1, 1999

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