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
› Author Affiliations
Further Information

Publication History

Received: 01 May 2013

Accepted after revision: 08 May 2013

Publication Date:
17 May 2013 (online)


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.

Supporting Information

 
  • References

  • 1 Bringmann G, Günther C, Ochse M, Schupp O, Tasler S. Biaryls in Nature In Progess in the Chemistry of Organic Natural Products . Vol. 82. Herz W, Falk H, Kirby GW, Moore RE. Springer; Vienna: 2001: 1-249
    • 2a Berthod M, Mignani G, Woodward G, Lemaire M. Chem. Rev. 2005; 105: 1801
    • 2b Li YM, Kwong FY, Yu WY, Chan AS. C. Coord. Chem. Rev. 2007; 251: 2119
    • 3a Chen Y, Yekta S, Yudin AK. Chem. Rev. 2003; 103: 3155
    • 3b Brunel JM. Chem. Rev. 2007; 107: PR1
  • 4 de Meijere A, Diederich F. In Metal-Catalyzed Cross-Coupling Reactions . Wiley-VCH; Weinheim: 2004. 2nd ed.
    • 5a Hayashi T, Hayashizaki K, Kiyoi T, Ito Y. J. Am. Chem. Soc. 1988; 110: 8153
    • 5b Hayashi T, Hayashizaki K, Ito Y. Tetrahedron Lett. 1989; 30: 215
    • 6a Frejd T, Klingstedt T. Acta Chem. Scand. 1989; 43: 670
    • 6b Terfort A, Brunner H. J. Chem. Soc., Perkin Trans. 1 1996; 1467
    • 6c Dahlenburg L, Kurth V. Inorg. Chim. Acta 2001; 319: 176

      For selected reviews, see:
    • 7a Bringmann G, Mortimer AJ. P, Keller PA, Gresser MJ, Garner J, Breuning M. Angew. Chem. Int. Ed. 2005; 44: 5384
    • 7b Wallace TW. Org. Biomol. Chem. 2006; 4: 3197
    • 7c Ogasawara M, Watanabe S. Synthesis 2009; 1761
    • 8a Cammidge AN, Crépy KV. L. Chem. Commun. 2000; 1723
    • 8b Cammidge AN, Crépy KV. L. Tetrahedron 2000; 1723
  • 9 Yin J, Buchwald SL. J. Am. Chem. Soc. 2000; 122: 12051

    • For selected examples, see:
    • 10a Mikami K, Miyamoto T, Hatano M. Chem. Commun. 2004; 2082
    • 10b Willis MC, Powell LH. W, Claverie CK, Watson SJ. Angew. Chem. Int. Ed. 2004; 43: 1249
    • 10c Genov M, Almrín A, Espinet P. Chem. Eur. J. 2006; 12: 9346
    • 10d Sawai K, Tatumi R, Nakahodo T, Fujihara H. Angew. Chem. Int. Ed. 2008; 47: 6017
    • 10e Bermejo A, Ros A, Fernandez R, Lassaletta JM. J. Am. Chem. Soc. 2008; 130: 15798
    • 10f Uozumi Y, Matsuura Y, Arakawa T, Yamada YM. A. Angew. Chem. Int. Ed. 2009; 48: 2708
    • 10g Shen X, Jones GO, Watson DA, Bhayana B, Buchwald SL. J. Am. Chem. Soc. 2010; 132: 11278
    • 10h Urbaneja X, Mercier A, Besnard C, Kundig EP. Chem. Commun. 2011; 47: 3739
    • 10i Zhang S, Wang Z, Xu M, Lin G. Org. Lett. 2010; 12: 5546
    • 10j Yamamoto T, Akai Y, Nagata Y, Suginome M. Angew. Chem. Int. Ed. 2011; 50: 8844
    • 10k Tang W, Patel ND, Xu G, Xu X, Savoie J, Ma S, Hao MH, Keshipeddy S, Capacci AG, Wei X, Zhang Y, Gao JJ, Li W, Rodriguez S, Lu BZ, Yee NK, Senanayake CH. Org. Lett. 2012; 14: 2258
    • 12a Kantchev EA. B, O’Brien CJ, Organ MG. Angew. Chem. Int. Ed. 2007; 46: 2768
    • 12b Marion N, Nolan SP. Acc. Chem. Res. 2008; 41: 1440
    • 12c Würtz S, Glorius F. Acc. Chem. Res. 2008; 41: 1523

      For reviews, see:
    • 13a César V, Bellemin-Laponnaz S, Gade LH. Chem. Soc. Rev. 2004; 33: 619
    • 13b Wang F, Liu L, Wang W, Li S, Shi M. Coord. Chem. Rev. 2012; 256: 804
    • 13c Benhamou L, Chardon E, Lavigne G, Bellemin-Laponnaz S, César V. Chem. Rev. 2011; 111: 2705
  • 14 Debono N, Labande A, Manoury E, Daran J, Poli R. Organometallics 2010; 29: 1879
  • 15 Shigeng G, Tang J, Zhang D, Wang Q, Chen Z, Weng L. J. Organomet. Chem. 2012; 700: 223
    • 16a Luan X, Mariz R, Robert C, Gatti M, Blumentritt S, Linden A, Dorta R. Org. Lett. 2008; 10: 5569
    • 16b Luan X, Wu L, Drinkel E, Mariz R, Gatti M, Dorta R. Org. Lett. 2010; 12: 1912

    • For other work on such naphthyl-substituted NHC, see:
    • 16c Luan X, Mariz R, Gatti M, Costabile C, Poater A, Cavallo L, Linden A, Dorta R. J. Am. Chem. Soc. 2008; 130: 6848
    • 16d Gatti M, Vieille-Petit L, Luan X, Mariz R, Drinkel E, Linden A, Dorta R. J. Am. Chem. Soc. 2009; 131: 9498
    • 16e Vieille-Petit L, Luan X, Gatti M, Blumentritt S, Linden A, Clavier H, Nolan SP, Dorta R. Chem. Commun. 2009; 3783
    • 16f Vieille-Petit L, Luan X, Mariz R, Blumentritt S, Linden A, Dorta R. Eur. J. Inorg. Chem. 2009; 1861
    • 16g Vieille-Petit L, Clavier H, Linden A, Blumentritt S, Nolan SP, Dorta R. Organometallics 2010; 29: 775
    • 16h Wu L, Drinkel E, Gaggia F, Capolicchio S, Linden A, Falivene L, Cavallo L, Dorta R. Chem. Eur. J. 2011; 17: 12886
    • 16i Gatti M, Wu L, Drinkel E, Gaggia F, Blumentritt S, Linden A, Dorta R. ARKIVOC 2011; (vi): 176
  • 17 Wu L, Falivene L, Drinkel E, Grant S, Linden A, Cavallo L, Dorta R. Angew. Chem. Int. Ed. 2012; 51: 2870
  • 18 CCDC 936764 [(Ra,Sa)-C)] contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
  • 19 The Suzuki–Miyaura coupling using the corresponding aryl iodide (2-iodotoluene) gave very similar results (81% yield, 27% ee).