Synthetic, structural, and catalytic studies of well-defined allyl 1,2,3-triazol-5-ylidene (tzNHC) palladium complexes

European Journal of Inorganic Chemistry

Volumn , Issue 9, 2012, Pages 1387-1393

  Terashima, Takahiro ^a   Inomata, Sayuri ^a   Ogata, Kenichi ^a   Fukuzawa, Shin Ichi ^a  

^a CHUO UNIVERSITY   (Japan)

Author keywords

Allyl ligands; Carbene ligands; Cross coupling; Homogeneous catalysis; Palladium

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; CHLORINE COMPOUNDS; PALLADIUM COMPOUNDS; ROOM TEMPERATURE; STRUCTURAL PROPERTIES; X RAY DIFFRACTION ANALYSIS; X RAY PHOTOELECTRON SPECTROSCOPY;

ALLYL LIGANDS; CARBENE LIGANDS; CARBENES; CROSS-COUPLINGS; HIGH ACTIVITY; HOMOGENEOUS CATALYSIS; IMIDAZOL; PALLADIUM COMPLEXES; PROPERTY; SUZUKI-MIYAURA COUPLING REACTION;

LIGANDS;

EID: 84858696340     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.201101383     Document Type: Article

References (45)

1. S. P. Nolan (Ed.), N-Heterocyclic Carbenes in Synthesis, Wiley-VCH, Weinheim, Germany, 2006.
2. S. Díez-González (Ed.), N-Heterocyclic Carbenes, from Laboratory Curiosities to Efficient Synthetic Tools, RSC, Cambridge, United Kingdom, 2011.
3. C. S. J. Cazin (Ed.), N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis, Springer, Dordrecht, Germany, 2011.
4. F. E. Hahn, M. C. Jahke, Angew. Chem. 2008, 120, 3166-3216; Angew. Chem. Int. Ed. 2008, 47, 3122 -3172.
5. W. Herrmann, Angew. Chem. 2002, 114, 1342-3263; Angew. Chem. Int. Ed. 2002, 41, 1290 -1309.
6. S. Díez-González, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612-3676.
7. S. Gründemann, A. Kovacevic, M. Albrecht, J. W. Faller, R. H. Crabtree, Chem. Commun. 2001, 2274-2275.
8. S. Gründemann, A. Kovacevic, M. Albrecht, J. W. Faller, R. H. Crabtree, J. Am. Chem. Soc. 2002, 124, 10473-10481.
9. H. Label, M. K. Janes, A. B. Charette, S. P. Nolan, J. Am. Chem. Soc. 2004, 126, 5046-5047.
10. L. Yang, A. Krüger, A. Neels, M. Albrecht, Organometallics 2008, 27, 3161-3171.
11. M. Heckenroth, A. Neels, M. G. Garnier, P. Aebi, A. W. Ehlers, M. Albrecht, Chem. Eur. J. 2009, 15, 9375-9386.
12. X. Xu, B. Xu, Y. Li, S. H. Hong, Organometallics 2010, 29, 6343-6349.
13. M. Iglesias, M. Albrecht, Dalton Trans. 2010, 39, 5213-5215.
14. P. Mathew, A. Neels, M. Albrecht, J. Am. Chem. Soc. 2008, 130, 13534-13535.
15. For a review see:, J. D. Crowley, A.-L. Lee, K. J. Kilpin, Aust. J. Chem. 2011, 64, 1118-1132.
16. G. Guisad-Barrious, J. Bouffard, B. Donnadieu, G. Bertrand, Angew. Chem. Int. Ed. 2010, 49, 4759-4762.
17. A. Prades, E. Peris, M. Albrecht, Organometallics 2011, 30, 1162-1167.
18. T. Nakamura, K. Ogata, S.-i. Fukuzawa, Chem. Lett. 2010, 39, 920-922.
19. S. Inomata, H. Hiroki, T. Terashima, K. Ogata, S.-i. Fukuzawa, Tetrahedron 2011, 67, 7263-7267.
20. U. Christmann, R. Vilar, Angew. Chem. 2005, 117, 370-378; Angew. Chem. Int. Ed. 2005, 44, 366 -374.
21. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056-2075; Angew. Chem. Int. Ed. 2001, 40, 2004 -2021.
22. C. W. TornÃe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064.
23. T. Nakamura, T. Terashima, K. Ogata, S.-i. Fukuzawa, Org. Lett. 2011, 13, 620-623.
24. M. S. Viciu, O. Navarro, R. F. Germaneau, R. A. Kelly III, W. Sommer, N. Marion, E. D. Stevens, L. Cavallo, S. P. Nolan, Organometallics 2004, 23, 1629-1635.
25. G. Guisado-Barrios, J. Bouffard, B. Donnadieu, G. Bertrand, Angew. Chem. Int. Ed. 2010, 49, 4759-4762.
26. J. Bouffard, B. K. Keitz, R. Tonner, G. Guisado-Barrios, G. Frenking, R. H. Grubbs, G. Bertrand, Organometallics 2011, 30, 2617-2627.
27. R. A. Kelly III, H. Clavier, S. Giudice, N. M. Scott, E. D. Stevens, J. Bordner, I. Samardjiev, C. D. Hoff, L. Cavallo, S. P. Nolan, Organometallics 2008, 27, 202-210.
28. A. R. Chianese, X. Li, M. C. Janzen, J. W. Faller, R. H. Crabtree, Organometallics 2003, 22, 1663-1667.
29. G. Guisado-Barrios, J. Bouffard, B. Donnadieu, G. Bertrand, Organometallics 2011, 30, 6017-6021.
30. A. Poulain, D. Canseco-Gonzales, R. Hynes-Roche, H. Müller-Bunz, O. Schuster, H. Stoeckli-Evans, A. Neels, M. Albrecht, Organometallics 2011, 30, 1021-1029.
31. 13C NMR spectra of the (allyl)(tzNHC)Pd complexes; the shifts for the carbene C atoms are: 166.6 (TPh), 169.7 (TMes), and 171.8 (TPr) ppm., V. Huynh, Y. Han, R. Jothibasu, J. A. Yang, Organometallics 2009, 28, 5395-5404.
32. M. Heckenroth, E. Kluser, A. Neels, M. Albrecht, Angew. Chem. 2007, 119, 6409-6412; Angew. Chem. Int. Ed. 2007, 46, 6293 -6296.
33. M. Heckenroth, A. Neels, M. G. Garnier, P. Aebi, A. W. Ehlers, M. Albrecht, Chem. Eur. J. 2009, 15, 9375-9386.
34. N. Marion, O. Navarro, J. Mei, E. D. Stevens, N. M. Scott, S. P. Nolan, J. Am. Chem. Soc. 2006, 128, 4101-4111.
35. G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, Angew. Chem. 2003, 115, 3818-3821; Angew. Chem. Int. Ed. 2003, 42, 3690 -3693.
36. O. Navarro, R. A. Kelly III, S. P. Nolan, J. Am. Chem. Soc. 2003, 125, 16194-16195.
37. C. Song, Y. Ma, Q. Chai, C. Ma, W. Jiang, M. B. Andrus, Tetrahedron 2005, 61, 7438-7446.
38. O. Diebolt, P. Braunstein, S. P. Nolan, C. S. J. Cazin, Chem. Commun. 2008, 3190-3192.
39. Z. Jin, S.-X. Guo, X.-P. Gu, L.-L. Qiu, H.-B. Song, J.-X. Fang, Adv. Synth. Catal. 2009, 351, 1575-1585.
40. L. Wu, E. Drinkel, F. Gaggia, S. Capolicchio, A. Linden, L. Falivene, L. Cavallo, R. Dorta, Chem. Eur. J. 2011, 17, 12886-12890.
41. S. C. Sau, S. Santra, T. K. Sen, S. K. Mandal, D. Koley, Chem. Commun. 2012,.
42. S. Fantasia, S. P. Nolan, Chem. Eur. J. 2008, 14, 6987-6993
43. CrystalStructure 4.0, Crystal Structure Analysis Package, Rigaku Corporation, Tokyo 196-8666, Japan, 2000-2010.
44. J. R. Carruthers, J. S. Rollett, P. W. Betterrigde, D. Pears, L. Larsen, E. Gabe, CRYSTALS, issue 11, Chemical Crystallography Laboratory, Oxford, UK, 1999.
45. SIR97:, A. Altomare, M. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi, A. Moliterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115-119.