Snapshot of a Chelation-Assisted C−H/Alkyne Coupling:  A Ruthenium Complex Caught in the Act of C−C Bond Formation

Laure Benhamou, Vincent César, Noël Lugan, and Guy Lavigne*
Laboratoire de Chimie de Coordination du CNRS, 205 Route de Narbonne, 31077 Toulouse Cedex, France
Organometallics, 2007, 26 (18), pp 4673–4676
DOI: 10.1021/om7005003
Publication Date (Web): August 4, 2007
Copyright © 2007 American Chemical Society
*

 Corresponding author. E-mail:  Guy.Lavigne@lcc-toulouse.fr.

Abstract

Abstract Image

The complex Ru(CO)2(PPh3)3 (1) reacts with o-(diphenylphosphanyl)benzaldehyde within 2 min at 20 °C to give the hydrido acyl complex Ru(H){P(C6H5)2(C6H4)C(O)}(CO)2(PPh3) (2) via selective activation of the C−H bond of the aldehyde function. Further addition of diphenylacetylene (110 °C, 3 h) affords the novel complex Ru{P(C6H5)2(C6H4)C(O)(C6H5)CCH(C6H5)}(CO){P(C6H5)3} (3), incorporating the newly assembled o-(diphenylphosphanyl)phenyl (E)-stilbenyl ketone ligand. The α,β-unsaturated ketone moiety of the latter is bound to the metal in an η4 coordination mode involving both a side-on coordination of the carbonyl group and a more classical η2 linkage of the olefinic bond. Both complexes were fully characterized by spectroscopic methods and by X-ray diffraction. The whole reaction sequence provides a valuable experimental model for the chelation-assisted hydroacylation of an alkyne with a tethered aldehyde.

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History

  • Published In Issue August 27, 2007
  • Received May 21, 2007

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