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DOI: 10.1055/s-2005-865369
Synthesis of 1-Phosphabarrelene Phosphine Sulfide Substituted Palladium(II) Complexes
Contributor(s): Victor Snieckus, Oleg M. DemchukEcole Polytechnique, Palaiseau, France
Synthesis of 1-Phosphabarrelene Phosphine Sulfide Substituted Palladium(II) Complexes: Application in the Catalyzed Suzuki Cross-Coupling Process in the Allylation of Secondary Amines
Organometallics 2005, 24: 1204-1213
Publication History
Publication Date:
20 July 2005 (online)
Key words
phosphinine - phosphabarrelene - crystallographic study - S,P-ligands
Significance
A general Diels-Alder-based synthesis of 1-phosphabarrelenes from substituted phosphinines is reported. Palladium complexes have been prepared which serve as good ligands for cross-coupling reactions and in the allylation of secondary amines with TON up to 7 × 106. X-ray crystal structural analysis and computational data of the complexes are presented.
Comment
The phosphabarrelenes, P-analogues of the classical barrelene (H. E. Zimmerman, R. M. Paufler J. Am. Chem. Soc. 1960, 82, 1514-1515) represent a unusual class of heterocycles and phosphorus ligands, which have received little attention (B. Breit, E. Fuchs Chem. Commun. 2004, 694-695). Aside from interest in its chemical reactivity, the three-dimensional heterocyclic core opens new horizons for rational ligand design not only for conventional Pd-catalyzed cross-coupling reactions but also for asymmetric catalytic processes.