Ureaphosphanes as hybrid, anionic or supramolecular bidentate ligands for asymmetric hydrogenation reactions

J. Meeuwissen, R. Detz, A. J. Sandee, B. de Bruin, M. A. Siegler, A.L. Spek, J.N.H. Reek

Research output: Contribution to journalArticleAcademicpeer-review

Abstract

We report the coordination behavior of ureaphosphane ligand 1-[2-(diphenylphosphanyl)ethyl]-3-phenylurea (L1) towards different rhodium precursor complexes. Depending on the nature of the anion and the ligand/metal ratio, L1 acts either as a hybrid P,O-coordinating chelate, as an anionic P,N-coordinating chelate or as a supramolecular (hydrogen-bonded) bidentate ligand. The different types of complexes were investigated in the asymmetric hydrogenation of three olefinic substrates using ureaphosphanes L2 and L3, which are chiral analogues of L1. For methyl 2-acetamidoacrylate (S1) and dimethyl itaconate (S2) the neutral complex [Rh(L2-κ2P,N)(cod)], containing an anionic P,N-coordinating ureaphosphane ligand, provided the best enantioselectivity (69.2 and 24.3 %, respectively). For N-(3,4-dihydro-2-naphthalenyl)acetamide (S3) the best enantioselectivity was obtained with the cationic complex [Rh(L3-κ2P,O)(nbd)]BF4, containing a hybrid P,O-coordinating ureaphosphane ligand (86.1 %).
Original languageEnglish
Pages (from-to)2992-2997
Number of pages6
JournalEuropean Journal of Inorganic Chemistry
Volume2010
Issue number19
DOIs
Publication statusPublished - 2010

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