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Novel P-stereogenic PCP pincer-aryl ruthenium(ii) complexes and their use in the asymmetric hydrogen transfer reaction of acetophenone

Medici, Serenella and Gagliardo, Marcella and Williams, Scott B. and Chase, Preston A. and Gladiali, Serafino Gabriele and Lutz, Martin and Spek, Anthony L. and Klink, Gerard P. M. van and Koten, Gerard van (2005) Novel P-stereogenic PCP pincer-aryl ruthenium(ii) complexes and their use in the asymmetric hydrogen transfer reaction of acetophenone. Helvetica Chimica Acta, Vol. 88 (3), p. 694-705. eISSN 1522-2675. Article.

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DOI: 10.1002/hlca.200590048

Abstract

Achiral P-donor pincer-aryl ruthenium complexes ([RuCl(PCP)(PPh3)]) 4c,d were synthesized via transcyclometalation reactions by mixing equivalent amounts of [1,3-phenylenebis(methylene)]bis[diisopropylphosphine] (2c) or [1,3-phenylenebis(methylene)]bis[diphenylphosphine] (2d) and the N-donor pincer-aryl complex [RuCl{2,6-(Me2NCH2)2C6H3}(PPh3)], (3; Scheme 2). The same synthetic procedure was successfully applied for the preparation of novel chiral P-donor pincer-aryl ruthenium complexes [RuCl(P*CP*)(PPh3)] 4a,b by reacting P-stereogenic pincer-arenes (S,S)-[1,3-phenylenebis(methylene)]bis[(alkyl)(phenyl)phosphines] 2a,b (alkyl=iPr or tBu, P*CHP*) and the complex [RuCl{2,6-(Me2NCH2)2C6H3}(PPh3)], (3; Scheme 3). The crystal structures of achiral [RuCl(iPr,iPrPCP)(PPh3)] 4c and of chiral (S,S)-[RuCl(tBu,PhPCP)(PPh3)] 4a were determined by X-ray diffraction (Fig. 3). Achiral [RuCl(PCP)(PPh3)] complexes and chiral [RuCl(P*CP*)(PPh3)] complexes were tested as catalyst in the H-transfer reduction of acetophenone with propan-2-ol. With the chiral complexes, a modest enantioselectivity was obtained.

Item Type:Article
ID Code:2494
Status:Published
Refereed:Yes
Uncontrolled Keywords:Multidentate phosphine ligands, transition metals, stereochemistry, enantioselectivity
Subjects:Area 03 - Scienze chimiche > CHIM/04 Chimica industriale
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:Wiley
eISSN:1522-2675
Copyright Holders:© 2005 Verlag Helvetica Chimica Acta
Deposited On:18 Aug 2009 10:07

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