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

Linglin Wu; Alvaro Salvador; Arnold Ou; Ming Wen Shi; Brian W. Skelton; Reto Dorta

doi:10.1055/s-0033-1338864

Synlett, Table of Contents

Synlett 2013; 24(10): 1215-1220
DOI: 10.1055/s-0033-1338864

cluster

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

Linglin Wu

^aOrganisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland

^bSchool 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

^aOrganisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland

^bSchool 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

^bSchool 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

^bSchool 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

^cCentre for Microscopy, Characterisation and Analysis, University of Western Australia, 6009 Crawley, Australia

,

Reto Dorta*

^aOrganisch-chemisches Institut, Universität Zürich, Winterthurerstrasse 190, 8057 Zürich, Switzerland

^bSchool 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

Abstract

All articles of this category

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

Full Text

References

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

11a Nolan SP. N-Heterocyclic Carbenes in Synthesis . Wiley-VCH; Weinheim: 2006
11b N-Heterocyclic Carbenes in Transition Metal Catalysis. Vol. 21. Glorius F. Springer; Berlin: 2007
11c Diez-Gonzalez S, Nolan SP. Chem. Rev. 2009; 109: 3612
11d N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis. Vol. 32. Cazin CS. J. Springer; Dordrecht: 2010

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).

Supplementary Material

Supporting Information