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Synlett 2013; 24(10): 1215-1220
DOI: 10.1055/s-0033-1338864
cluster
© Georg Thieme Verlag Stuttgart · New York

Monodentate Chiral N-Heterocyclic Carbene–Palladium-Catalyzed Asymmetric Suzuki–Miyaura and Kumada Coupling

Linglin Wu
a   Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland
b   School of Chemistry and Biochemistry, University of Western Australia, 35 Stirling Highway, 6009 Crawley, Australia   Fax: +61(8)64887330   Email: reto.dorta@uwa.edu.au
,
Alvaro Salvador
a   Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland
b   School of Chemistry and Biochemistry, University of Western Australia, 35 Stirling Highway, 6009 Crawley, Australia   Fax: +61(8)64887330   Email: reto.dorta@uwa.edu.au
,
Arnold Ou
b   School of Chemistry and Biochemistry, University of Western Australia, 35 Stirling Highway, 6009 Crawley, Australia   Fax: +61(8)64887330   Email: reto.dorta@uwa.edu.au
,
Ming Wen Shi
b   School of Chemistry and Biochemistry, University of Western Australia, 35 Stirling Highway, 6009 Crawley, Australia   Fax: +61(8)64887330   Email: reto.dorta@uwa.edu.au
,
Brian W. Skelton
c   Centre for Microscopy, Characterisation and Analysis, University of Western Australia, 6009 Crawley, Australia
,
Reto Dorta*
a   Organisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland
b   School of Chemistry and Biochemistry, University of Western Australia, 35 Stirling Highway, 6009 Crawley, Australia   Fax: +61(8)64887330   Email: reto.dorta@uwa.edu.au
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Further Information

Publication History

Received: 01 May 2013

Accepted after revision: 08 May 2013

Publication Date:
17 May 2013 (online)

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Abstract

N-Heterocyclic carbene ligands derived from C 2-symmetric diamine with naphthyl side chains are introduced as chiral monodentate ligands, and their palladium complexes (NHC)Pd(cin)Cl are prepared. These compounds exist as a mixture of diastereomers, and the palladium complexes can be successfully separated. When used in the asymmetric Suzuki–Miyaura and ­Kumada coupling, chiral biaryls can be obtained in high yield and moderate selectivity.

Key words

monodentate chiral NHC - palladium - asymmetric ­catalysis - Suzuki–Miyaura coupling - Kumada coupling

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

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