A new tetratertiary phosphine ligand and its use in Pd-catalyzed allylic substitution.
A new tetraphosphine, the cis-cis-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane (Tedicyp) 1 has been synthesized, characterized, and used in Pd-catalyzed allylic substitutions. The Tedicyp was easily prepared in seven steps from the commercially available himic anhydride. The structure of the complex Tedicyp-borane was determined by X-ray analysis. The tetraphosphine in combination with [Pd(eta(3)-C(3)H(5))Cl](2) affords a very efficient catalyst for allylic substitution of several allylic acetates. Under mild conditions, very high turnover numbers and turnover frequencies have been obtained.
Laboratoire de Synthèse Organique, UMR-CNRS 6009, Faculté de St-Jérôme, 13397 Marseille Cedex 20, France.
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Laurenti
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Feuerstein
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Pèpe
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Doucet
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Santelli