[structure: see text] Phosphorinanes are presented as a class of phosphine ligand suitable for organopalladium cross-coupling chemistry. Prepared via a direct double Michael addition of a monoalkyl- or arylphosphine to phorone followed by a Wolf-Kishner reduction, phosphorinanes are relatively inexpensive to manufacture and allow modification of one of the alkyl moieties permitting steric and electronic fine-tuning of the ligands. Library screening and applications of these ligands in the Suzuki, Sonogashira, ketone arylation, and aryl amination reactions are presented.

Polyphenyl derivatives Q 0700Phosphorinanes as Ligands for Palladium-Catalyzed Cross-Coupling Chemistry. -The title catalysts (I) are effective in Suzuki and Sonogashira cross-coupling reactions, ketone arylation and aryl amination reactions. -(BRENSTRUM, T.; CLATTENBURG, J.; BRITTEN, J.; ZAVORINE, S.; DYCK, J.; ROBERTSON, A. J.; MCNULTY*, J.; CAPRETTA, A.; Org. Lett. 8 (2006) 1, 103-105; Dep. Chem., McMaster Univ., Hamilton, Ont. L8S 4M1, Can.; Eng.) -R. Steudel 20-085

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The title reagents effectively promote the esterification of aromatic acids with optically active secondary alcohols. Major advantage of this new method is the fact that the inversion-to-retention ratio of the products can be controlled by the steric properties of the alkyl substituents at the phosphorane. Thus, high level of retention is achieved with butyl and iso-butyl phosphoranes [cf. (III), (VII)] while the small ethyl substituent increases the inversion levels [cf. (VIII)] (16th international conference on phosphorus chemistry). -(DYCK*, J.; ZAVORINE, S.; ROBERTSON, A. J.; CAPRETTA, A.; LARICHEV, V.; BRITTEN, J.; MCNULTY, J.; J. Organomet. Chem. 690 (2005) 10, 2548-2552; Cytec Canada Inc., Niagara Falls, Ont. L2E 6T4, Can.; Eng.) -Mischke 41-176