Imidazo[1,5-a]pyridine-3-ylidenes - Pyridine derived N-heterocyclic carbene ligands

Tetrahedron

Volumn 61, Issue 26, 2005, Pages 6207-6217

  Burstein, Christian ^a,b   Lehmann, Christian W ^a   Glorius, Frank ^a,b  

^a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG   (Germany)

^b PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Ligand design; N heterocyclic carbene; Suzuki Miyaura cross coupling

Indexed keywords

BROMINE DERIVATIVE; CARBENOID; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; IMIDAZOLIUM BROMIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; GEOMETRY; INFRARED SPECTROSCOPY; PRECURSOR; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SUZUKI REACTION; SYNTHESIS; X RAY ANALYSIS;

EID: 20444492841     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.03.115     Document Type: Article

References (32)

1. For excellent reviews on the use of NHC ligands in catalysis, see: (a) W.A. Herrmann Angew. Chem. Int., Ed. 41 2002 1290
2. W.A. Herrmann, and C. Köcher Angew. Chem. Int., Ed. 36 1997 2162
3. See also, (c) A.J. Arduengo III, and R. Krafczyk Chem. Unserer Zeit 32 1998 6
4. D. Bourissou, O. Guerret, F.P. Gabbaï, and G. Bertrand Chem. Rev. 100 2000 39
5. A.C. Hillier, G.A. Grasa, M.S. Viciu, H.M. Lee, C. Yang, and S.P. Nolan J. Organomet. Chem. 653 2002 69 82
6. For some applications of sterically demanding NHC ligands, see: (a) C.W.K. Gstöttmayr, V.P.W. Böhm, E. Herdtweck, M. Grosche, and W.A. Herrmann Angew. Chem. Int., Ed. 41 2002 1363
7. M. Eckhardt, and G. Fu J. Am. Chem. Soc. 125 2003 13642
8. Y. Ma, C. Song, W. Jiang, Q. Wu, Y. Wang, X. Liu, and M.B. Andrus Org. Lett. 5 2003 3317
9. G. Altenhoff, R. Goddard, C.W. Lehmann, and F. Glorius Angew. Chem. Int., Ed. 42 2003 3690
10. G. Altenhoff, R. Goddard, C.W. Lehmann, and F. Glorius J. Am. Chem. Soc. 126 2004 15195
11. R. Weiss, S. Reichel, M. Handke, and F. Hampel Angew. Chem. Int., Ed. 37 1998 344
12. F. Glorius, G. Altenhoff, R. Goddard, and C. Lehmann Chem. Commun. 2002 2704
13. α-radiation (λ=0.71073 Å) and a rotating anode (FR 591) from the same manufacturer. The crystal was mounted on the tip of a glass fibre using viscous perfluoropolyether (Lancaster) and cooled in a stream of cold nitrogen gas. The structures were solved by direct methods (SHELXS-97; G.M. Sheldrick, Program for the determination of crystal structures, University of Göttingen, Germany, 1997)
14. -3. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 256664 (7), CCDC 256665 (5b), CCDC 256666 (8), CCDC 256667 (5a), CCDC 256668 (9). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: 144-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
15. s symmetry resulting in the mutual disorder of the bridging carbon and nitrogen atom. This disorder was taken into account in the structure refinement, by equivalencing the shared C/N position and displacement parameter with a 1:1 site occupation.
16. F. Diederich A. de Meijere Metal-catalyzed Cross-coupling Reactions 2004 Wiley New York
17. W.A. Herrmann, M. Elison, J. Fischer, C. Köcher, and G.R.J. Artus Angew. Chem. Int., Ed. Engl. 34 1995 2371
18. D. Enders, and H. Gielen J. Organomet. Chem. 70 2001 617 618 The triflate salt of 5a was employed for this reaction
19. Because of their sensitivity and lability, the iridium complex 8 and the palladium complex 9 were not fully characterized. In the case of 8, the formation of a small amount of the corresponding chloro complex can not be excluded.
20. F. Glorius Angew. Chem. Int., Ed. 43 2004 3364
21. C.S. Slone, D.A. Weinberger, and C.A. Mirkin Prog. Inorg. Chem. 48 1999 233
22. J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, and M. Lemaire Chem. Rev. 102 2002 1359
23. S. Kotha, K. Lahiri, and D. Kashinath Tetrahedron 58 2002 9633
24. N. Miyaura, and A. Suzuki Chem. Rev. 95 1995 2457
25. A. Suzuki J. Organomet. Chem. 576 1999 147
26. N. Miyaura Top. Curr. Chem. 219 2002 11
27. For a review on Pd-catalyzed cross-coupling reactions of aryl chlorides, see: (a) A.F. Littke, and G.C. Fu Angew. Chem. Int., Ed. 41 2002 4176
28. See also: (b) M. Miura Angew. Chem. Int., Ed. 43 2004 2201
29. The importance of monoligated Pd(0) complexes as catalytically active species in Suzuki-Miyaura cross-coupling has been proposed. See, for example: (a) A.F. Littke, C. Dai, and G.C. Fu J. Am. Chem. Soc. 122 2000 4020
30. J.P. Stambuli, R. Kuwano, and J.F. Hartwig Angew. Chem. Int., Ed. 41 2002 4746
31. Q.-S. Hu, Y. Lu, Z.-Y. Tang, and H.-B. Yu J. Am. Chem. Soc. 125 2003 2856
32. The 2,6-dimethoxyphenyl group was also used in an exceptionally practical and general catalyst system for the Suzuki-Miyaura cross-coupling: S.D. Walker, T.E. Barder, J.R. Martinelli, and S.L. Buchwald Angew. Chem. Int., Ed. 43 2004 1871