Synthesis and structures of copper(I) complexes with phosphino- functionalized N-heterocyclic carbenes (NHCP) and bis-N-heterocyclic carbenes (Bis-NHC)

Organometallics

Volumn 31, Issue 22, 2012, Pages 8000-8011

  Kühnel, Erik ^a   Shishkov, Igor V ^a   Rominger, Frank ^a   Oeser, Thomas ^a   Hofmann, Peter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANALOGOUS REACTIONS; CARBENES; CHARGED COMPLEXES; COPPER COMPLEXES; DIMERIC SPECIES; DINUCLEAR; DINUCLEAR COMPLEX; FUNCTIONALIZED; METALLACYCLES; N-HETEROCYCLIC CARBENES; NHC LIGANDS; STRUCTURAL MOTIFS; SUBSTITUTION PATTERNS;

COPPER; COPPER COMPOUNDS; LIGANDS; ORGANIC COMPOUNDS; X RAY DIFFRACTION;

SYNTHESIS (CHEMICAL);

EID: 84870005673     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om300701u     Document Type: Article

References (86)

1. Pyykkö, P. Chem. Rev. 1997, 597
2. Pyykkö, P.; Mendizabal, F. Chem. Eur. J. 1997, 3, 1458
3. Pyykkö, P.; Runeberg, N.; Mendizabal, F. Chem. Eur. J. 1997, 3, 1451
4. Pyykkö, P.; Zhao, Y. Angew. Chem., Int. Ed. 1991, 30, 604
5. Pyykko, P. Chem. Rev. 1988, 88, 563
6. Merz, K. M.; Hoffmann, R. Inorg. Chem. 1988, 27, 2120
7. Mehrotra, P. K.; Hoffmann, R. Inorg. Chem. 1978, 17, 2187
8. Fernández, E. J.; López-de-Luzuriaga, J. M.; Monge, M.; Rodríguez, M. A. Inorg. Chem. 1998, 37, 6002
9. Poblet, J.-M.; Bénard, M. Chem. Commun. 1998, 1179
10. Carvajal, M. A.; Alvarez, S.; Novoa, J. J. Chemistry 2004, 10, 2117
11. O'Grady, E.; Kaltsoyannis, N. Phys. Chem. Chem. Phys. 2004, 6, 680
12. Cotton, F. A.; Feng, X.; Timmons, D. J. Inorg. Chem. 1998, 37, 4066
13. Lee, S. W.; Trogler, W. C. Inorg. Chem. 1990, 29, 1659
14. Cotton, F. A.; Feng, X.; Matusz, M.; Poli, R. J. Am. Chem. Soc. 1988, 110, 7077
15. Fränkel, R.; Kniczek, J.; Ponikwar, W.; Nöth, H.; Polborn, K.; Fehlhammer, W. P. Inorg. Chim. Acta 2001, 312, 23
16. Hu, X.; Castro-Rodriguez, I.; Meyer, K. J. Am. Chem. Soc. 2003, 125, 12237
17. Matsumoto, K.; Matsumoto, N.; Ishii, A.; Tsukuda, T.; Hasegawa, M.; Tsubomura, T. Dalton Trans. 2009, 6795
18. Poyatos, M.; Mata, J. A.; Peris, E. Chem. Rev. 2009, 109, 3677
19. Venkatachalam, G.; Heckenroth, M.; Neels, A.; Albrecht, M. Helv. Chim. Acta 2009, 1034
20. Ellul, C. E.; Reed, G.; Mahon, M. F.; Pascu, S. I.; Whittlesey, M. K. Organometallics 2010, 29, 4097
21. Catalano, V. J.; Munro, L. B.; Strasser, C. E.; Samin, A. F. Inorg. Chem. 2011, 50, 8465
22. Tubaro, C.; Biffis, A.; Gava, R.; Scattolin, E.; Volpe, A.; Basato, M.; Díaz-Requejo, M. M.; Perez, P. J. Eur. J. Org. Chem. 2012, 2012, 1367
23. Che, C.-M.; Mao, Z.; Miskowski, V. M.; Tse, M.-C.; Chan, C.-K.; Cheung, K. K.; Phillips, D. L.; Leung, K.-H. Angew. Chem., Int. Ed. 2000, 39, 4084
24. Mao, M. Z.; Chao, H. Y.; Che, C. M.; Fu, W. F.; Cheung, K. K.; Zhu, N. Chem. Eur. J. 2003, 9, 2885
25. Phillips, D. L.; Che, C.-M.; Leung, K. H.; Mao, Z.; Tse, M.-C. Coord. Chem. Rev. 2005, 249, 1476
26. Straub, B. F.; Rominger, F.; Hofmann, P. Inorg. Chem. 2000, 39, 2113
27. Kühl, O. Chem. Soc. Rev. 2007, 36, 592
28. Albert, K.; Gisdakis, P.; Rösch, N. Organometallics 1998, 17, 1608
29. Herrmann, W. A.; Kocher, C.; Gooßen, L. J.; Artus, G. R. J. Chem. Eur. J. 1996, 2, 1627
30. Yang, C.; Lee, H. M.; Nolan, S. P. Org. Lett. 2001, 3, 1511
31. Danopoulos, A. A.; Winston, S.; Gelbrich, T.; Hursthouse, M. B.; Tooze, R. P. Chem. Commun. 2002, 482
32. Tsoureas, N.; Danopoulos, A. A.; Tulloch, A. A. D.; Light, M. E. Organometallics 2003, 22, 4750
33. Lee, H. M.; Chiu, P. L.; Zeng, J. Y. Inorg. Chim. Acta 2004, 357, 4313
34. Lee, H. M.; Zeng, J. Y.; Hu, C.-H.; Lee, M.-T. Inorg. Chem. 2004, 43, 6822
35. Wang, A.-E.; Zhong, J.; Xie, J.-H.; Li, K.; Zhou, Q.-L. Adv. Synth. Catal. 2004, 346, 595
36. Field, L. D.; Messerle, B. A.; Vuong, K. Q.; Turner, P. Organometallics 2005, 24, 4241
37. Wang, A.-E.; Xie, J.-H.; Wang, L.-X.; Zhou, Q.-L. Tetrahedron 2005, 61, 259
38. Hahn, F. E.; Jahnke, M. C.; Pape, T. Organometallics 2006, 25, 5927
39. Wolf, J.; Labande, A.; Daran, J.-C.; Poli, R. J. Organomet. Chem. 2006, 691, 433
40. Zhou, Q.-L.; Zhong, J.; Xie, J.-H.; Wang, A.-E.; Zhang, W. Synlett 2006, 8, 1193
41. Lee, C. C.; Ke, W. C.; Chan, K. T.; Lai, C. L.; Hu, C. H.; Lee, H. M. Chem. Eur. J. 2007, 13, 582
42. Miranda-Soto, V.; Grotjahn, D. B.; DiPasquale, A. G.; Rheingold, A. L. J. Am. Chem. Soc. 2008, 130, 13200
43. Shaghafi, M. B.; Kohn, B. L.; Jarvo, E. R. Org. Lett. 2008, 10, 4743
44. Wolf, J.; Labande, A.; Daran, J.-C.; Poli, R. Eur. J. Inorg. Chem. 2008, 3024
45. Benhamou, L.; Wolf, J.; César, V.; Labande, A.; Poli, R.; Lugan, N.; Lavigne, G. Organometallics 2009, 28, 6981
46. Hahn, F. E.; Naziruddin, R. A.; Hepp, A.; Pape, T. Organometallics 2010, 29, 5283
47. Cabeza, J. A.; Damonte, M.; García-álvarez, P.; Kennedy, A. R.; Pérez-Carreño, E. Organometallics 2011, 30, 826
48. Cabeza, J. A.; Damonte, M.; García-álvarez, P.; Hernández-Cruz, M. G.; Kennedy, A. R. Organometallics 2012, 31, 327
49. Lang, H.; Vittal, J. J.; Leung, P.-H. Dalton Trans. 1998, 2109
50. Focken, T.; Raabe, G.; Bolm, C. Tetrahedron: Asymmetry 2004, 15, 1693
51. Helmchen, G.; Bappert, E. Synlett 2004, 1789
52. Gischig, S.; Togni, A. Organometallics 2004, 23, 2479
53. Becht, J.-M.; Bappert, E.; Helmchen, G. Adv. Synth. Catal. 2005, 347, 1495
54. Bolm, C.; Focken, T.; Rudolph, J. Synthesis 2005, 2005, 429
55. Gischig, S.; Togni, A. Eur. J. Inorg. Chem. 2005, 2005, 4745
56. Hodgson, R.; Douthwaite, R. E. J. Organomet. Chem. 2005, 690, 5822
57. Gischig, S.; Togni, A. Organometallics 2005, 24, 203.
58. Shi, J.-C.; Yang, P.-Y.; Tong, Q.; Wu, Y.; Peng, Y. J. Mol. Catal. A: Chem. 2006, 259, 7
59. Nanchen, S.; Pfaltz, A. Helv. Chim. Acta 2006, 89, 1559
60. Labande, A.; Daran, J.-C.; Manoury, E.; Poli, R. Eur. J. Inorg. Chem. 2007, 2007, 1205
61. Visentin, F.; Togni, A. Organometallics 2007, 26, 3746
62. Shi, J. C.; Yang, P.; Tong, Q.; Jia, L. Dalton Trans. 2008, 938
63. Willms, H.; Frank, W.; Ganter, C. Chem. Eur. J. 2008, 14, 2719
64. We have developed a new, efficient and highly modular synthetic route to enantiopure P-chiral NHCP ligands: Brill, M; Hanno-Igels, P.; Hofmann, P. Manuscript in preparation.
65. Nägele, P.; Herrlich (née Blumbach), U.; Rominger, F.; Hofmann, P. Manuscript in preparation, 2012,.
66. Salem, H.; Herrlich (née Blumbach), U.; Kühnel, E.; Brill, M; Nägele, P.; Bogado, A. L.; Rominger, F.; Hofmann, P. Organometallics 2012, in press.
67. Marchenko, A. P.; Koidan, H. N.; Huryeva, A. N.; Zarudnitskii, E. V.; Yurchenko, A. A.; Kostyuk, A. N. J. Org. Chem. 2010, 75, 7141
68. Marchenko, A. P.; Koidan, H. N.; Pervak, I. I.; Huryeva, A. N.; Zarudnitskii, E. V.; Tolmachev, A. A.; Kostyuk, A. N. Tetrahedron Lett. 2012, 53, 494
69. Hillier, A. C.; Sommer, W. J.; Yong, B. S.; Petersen, J. L.; Cavallo, L.; Nolan, S. P. Organometallics 2003, 22, 4322
70. Díez-González, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874
71. Poater, A.; Cosenza, B.; Correa, A.; Giudice, S.; Ragone, F.; Scarano, V.; Cavallo, L. Eur. J. Inorg. Chem. 2009, 2009, 1759
72. Clavier, H.; Nolan, S. P. Chem. Commun. 2010, 46, 841
73. Droge, T.; Glorius, F. Angew. Chem., Int. Ed. 2010, 49, 6940
74. Tolman, C. A. Chem. Rev. 1977, 77, 313
75. Shishkov, I. V.; Rominger, F.; Hofmann, P. Dalton Trans. 2009, 1428
76. Tulloch, A. A. D.; Danopoulos, A. A.; Kleinhenz, S.; Light, M. E.; Hursthouse, M. B.; Eastham, G. Organometallics 2001, 20, 2027
77. Schneider, N.; César, V.; Bellemin-Laponnaz, S.; Gade, L. H. J. Organomet. Chem. 2005, 690, 5556
78. Fu, W. F.; Gan, X.; Che, C. M.; Cao, Q. Y.; Zhou, Z. Y.; Zhu, N. N. Chem. Eur. J. 2004, 10, 2228
79. Scherer, M.; Stein, D.; Breher, F.; Geier, J.; Schönberg, H.; Grützmacher, H. Z. Anorg. Allg. Chem. 2005, 631, 2770
80. Mézailles, N.; Le Floch, P.; Waschbüsch, K.; Ricard, L.; Mathey, F.; Kubiak, C. P. J. Organomet. Chem. 1997, 541, 277
81. Matsumoto, K.; Matsumoto, N.; Ishii, A.; Tsukuda, T.; Hasegawa, M.; Tsubomura, T. Dalton Trans. 2009, 6795
82. Hu, X.; Castro-Rodriguez, I.; Meyer, K. J. Am. Chem. Soc. 2003, 12237
83. Fränkel, R.; Kniczek, J.; Ponikwar, W.; Nöth, H.; Polborn, K.; Fehlhammer, W. P. Inorg. Chim. Acta 2001, 312, 23
84. Kühnel, E. Ongoing Ph.D. thesis, University of Heidelberg, Heidelberg, Germany.
85. Sheldrick, G. M. SADABS; Bruker Analytical X-ray Division, Madison, WI, 2008.
86. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112