New bicyclic phosphorous ligands: synthesis, structure and catalytic applications in ionic liquids

New azadioxaphosphabicyclo[3.3.0]octane ligands showing a trans arrangement with regard to the two five-membered heterocycles, were obtained as a mixture of three conformers, in agreement with molecular modelling studies. The stability of oxaphosphane ligands was studied under basic catalytic conditions, monitored by NMR spectroscopy. Palladium catalytic systems containing these ligands were active in Suzuki C-C cross-coupling reactions between phenylboronic acid and aryl halides (bromide and chloride derivatives) bearing electron-donor or electron-withdrawing substituents, in both organic and ionic liquid solvents. The catalytic systems showed a high stability even under the most severe reaction conditions used in this work. The ionic liquid catalytic phase could be recycled up to ten times without significant activity loss. (C) 2010 Elsevier Ltd. All rights reserved.