N-heterocyclic carbene-copper(I) complexes in homogeneous catalysis

Synlett

Volumn , Issue 14, 2007, Pages 2158-2167

  Díez González, Silvia ^a   Nolan, Steven P ^a  

^a INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

Copper; Diazo compounds; Homogeneous catalysis; Hydrosilylation; N heterocyclic carbene

Indexed keywords

CARBENOID; COPPER DERIVATIVE; HETEROCYCLIC COMPOUND; LIGAND;

CATALYSIS; COMPLEX FORMATION; CROSS COUPLING REACTION; REVIEW;

EID: 34548792833     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-985577     Document Type: Review

References (109)

1. (a) Wanzlick, H.-W. Angew. Chem., Int. Ed. Engl. 1962, 1, 75;
2. Angew. Chem. 1962, 74, 129.
3. (b) Wanzlick, H.-W.; Esser, F.; Kleiner, H.-J. Chem. Ber. 1963, 96, 1208.
4. (c) Wanzlick, H.-W.; Schönherr, H.-J. Angew. Chem., Int. Ed. Engl. 1968, 7, 141.
5. (a) Öfele, K. J. Organomet. Chem. 1968, 12, P42.
6. (b) Öfele, K. Angew. Chem., Int. Ed. Engl. 1970, 9, 739.
7. (c) Öfele, K. J. Organomet. Chem. 1970, 22, C9.
8. (a) Arduengo, A. J. III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
9. (b) Arduengo, A. J. III Acc. Chem. Res. 1999, 32, 913.
10. Tolman, C. A. Chem. Rev. 1997, 77, 313.
11. (a) Cavallo, L.; Correa, A.; Costabile, C.; Jacobsen, H. J. Organomet. Chem. 2005, 690, 5407.
12. (b) Díez-González, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874.
13. Marion, N.; Díez-González, S.; Nolan, S. P. Angew. Chem. Int. Ed. 2007, 46, 2988.
14. Green, J. C.; Scur, R. G.; Arnold, P. L.; Cloke, G. N. Chem. Commun. 1997, 1963.
15. (a) Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239.
16. (b) César, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619.
17. (c) Díez-González, S.; Nolan, S. P. Annu. Rep. Prog. Chem., Sect. B: Org. Chem. 2005, 101, 171.
18. (d) Nolan, S. P. N-Heterocyclic Carbenes in Synthesis; Wiley-VCH: Weinheim, 2006.
19. (e) Glorius, F. N-Heterocyclic Carbenes in Transition Metal Catalysis; Springer: Berlin, 2007.
20. Arduengo, A. J. III; Dias, H. V. R.; Calabrese, J. C.; Davidson, F. Organometallics 1993, 12, 3405.
21. (a) Raubenheimer, H. G.; Cronje, S.; van Rooyen, P. H.; Olivier, P. J.; Toerien, J. G. Angew. Chem., Int. Ed. Engl. 1994, 33, 672.
22. (b) Raubenheimer, H. G.; Cronje, S.; Olivier, P. J. J. Chem. Soc., Dalton Trans. 1995, 313.
23. For representative examples of copper-halogen complexes, see: (a) Jurkauskas, V.; Sadighi, J. P.; Buchwald, S. L. Org. Lett. 2003, 5, 2417.
24. (b) Kaur, H.; Zinn, F. K.; Stevens, E. D.; Nolan, S. P. Organometallics 2004, 23, 1157.
25. (c) Díez-González, S.; Kaur, H.; Zinn, F. K.; Stevens, E. D.; Nolan, S. P. J. Org. Chem. 2005, 70, 4784.
26. For copper acetate complexes, see: (d) Mankad, N. P.; Gray, T. G.; Laitar, D. S.; Sadighi, J. P. Organometallics 2004, 23, 1191.
27. Ren, H.; Zhao, X.; Xu, S.; Song, H.; Wang, B. J. Organomet. Chem. 2006, 691, 4109.
28. For copper tert-butoxide complexes, see: (a) Mankad, N. P.; Laitar, D. S.; Sadighi, J. P. Organometallics 2004, 23, 3369.
29. For copper ethoxide and phenoxide complexes, see: (b) Goj, L. A.; Blue, E. D.; Munro-Leighton, C.; Gunnoe, B.; Petersen, J. L. Inorg. Chem. 2005, 44, 8647.
30. Laitar, D. S.; Müller, P.; Sadighi, J. P. J. Am. Chem. Soc. 2005, 127, 17196.
31. Welle, A.; Díez-González, S.; Tinant, B.; Nolan, S. P.; Riant, O. Org. Lett. 2006, 8, 6059.
32. Wurtz, A. Ann. Chim. Phys. 1844, 11, 250.
33. Bezman, S. A.; Churchill, M. R.; Osborn, J. A.; Wormald, J. J. Am. Chem. Soc. 1971, 93, 2063.
34. Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291.
35. Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818.
36. (a) Lipshutz, B. H.; Keith, J.; Papa, P.; Vivian, R. Tetrahedron Lett. 1998, 39, 4627.
37. (b) Lipshutz, B. H.; Chrisman, W.; Noson, K.; Papa, P.; Sclafani, J. A.; Vivian, R. W.; Keith, J. M. Tetrahedron 2000, 56, 2779.
38. (a) Lipshutz, B. H.; Chrisman, W.; Noson, K. J. Organomet. Chem. 2001, 624, 367.
39. (b) Lipshutz, B. H.; Caires, C. C.; Kuipers, P.; Chrisman, W. Org. Lett. 2003, 5, 3085.
40. (a) Wishka, D. G.; Graber, D. R.; Seest, E. P.; Dolak, F. H.; Watt, W.; Morris, J. J. Org. Chem. 1998, 63, 7851.
41. (b) Deeter, J.; Frazier, J.; Staten, G.; Staszak, M.; Weigel, L. Tetrahedron Lett. 1990, 31, 7101.
42. (c) Labelle, M.; Belley, M.; Gareau, Y.; Gauthier, J. Y.; Guay, D.; Gordon, R.; Grossman, S. G.; Jones, T. R.; Leblanc, Y.; McAuliffe, M.; McFarlane, C.; Masson, P.; Metters, K. M.; Ouimet, N.; Patrick, D. H.; Piechuta, H.; Rochette, C.; Sawyer, N.; Xiang, Y. B.; Pickett, C. B.; Ford-Hutchinson, A. W.; Zamboni, R. J.; Young, R. N. Bioorg. Med. Chem. Lett. 1995, 5, 283.
43. Bantu, B.; Wang, D.; Wurst, K.; Buchmeiser, M. R. Tetrahedron 2005, 61, 12145.
44. Lorenz, C.; Schubert, U. Chem. Ber. 1995, 128, 1267.
45. (a) Pagenkopf, B. L.; Krüger, J.; Stojanovic, A.; Carreira, E. M. Angew. Chem. Int. Ed. 1998, 37, 3124.
46. (b) See also ref. 22.
47. (a) Moritami, Y.; Appella, D. H.; Jurkauskas, V.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 6797.
48. (b) Yun, J.; Buchwald, S. L. Org. Lett. 2001, 3, 1129.
49. (a) Chiu, P.; Chen, B.; Cheng, K. F. Tetrahedron Lett. 1998, 39, 9229.
50. (b) Chiu, P.; Szeto, C.-P.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901.
51. (c) Chiu, P.; Szeto, C. P.; Geng, Z.; Cheng, K. F. Tetrahedron Lett. 2001, 42, 4091.
52. (a) Chiu, P.; Leung, S. K. Chem. Commun. 2004, 2308.
53. (b) Chiu, P. Synthesis 2004, 2210.
54. (a) Lam, H. W.; Joensuu, P. M. Org. Lett. 2005, 7, 4225.
55. (b) Deschamp, J.; Chuzel, O.; Hannedouche, J.; Riant, O. Angew. Chem. Int. Ed. 2006, 45, 1292.
56. (c) Zhao, D. B.; Oisaki, K.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2006, 47, 1403.
57. (d) Chuzel, O.; Deschamp, J.; Chausteur, C.; Riant, O. Org. Lett. 2006, 8, 5943.
58. Deutsch, C.; Lipshutz, B. H.; Krause, N. Angew. Chem. Int. Ed. 2007, 46, 1650.
59. Smith, M. B.; March, J. Advanced Organic Chemistry: Reactions, Mechanism, and Structure, 5th ed.; Wiley-Interscience: New York, 2001.
60. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York, 1998.
61. Fructos, M. R.; Belderrain, T. R.; Nicasio, M. C.; Nolan, S. P.; Kaur, H.; Díaz-Requejo, M. M.; Pérez, P. J. J. Am. Chem. Soc. 2004, 126, 10846.
62. Formation of the homocoupling byproduct had occurred with the previously reported copper(I) complexes, see ref. 32.
63. Gawley, R. E.; Narayan, S. Chem. Commun. 2005, 5109.
64. (a) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599.
65. (b) Díaz-Requejo, M. M.; Pérez, P. J. J. Organomet. Chem. 2001, 617, 110.
66. (c) Borriero, C.; Cucciolito, M. E.; Panunzi, A.; Ruffo, F. Tetrahedron: Asymmetry 2001, 12, 2467.
67. Trost, B. M.; Dong, G. J. Am. Chem. Soc. 2006, 128, 6054.
68. Kelly, S. E. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I.; Schreiber, S. L., Eds.; Pergamon: Oxford, 1991, 729.
69. (a) Fujimura, O.; Honma, T. Tetrahedron Lett. 1998, 39, 625.
70. (b) Graban, E.; Lemke, F. R. Organometallics 2002, 21, 3823.
71. (c) Sun, W.; Kuhn, F. E. Appl. Catal., A 2005, 285, 163.
72. (d) Sun, W.; Yu, B. S.; Kuhn, F. E. Tetrahedron Lett. 2006, 47, 1993.
73. (a) Lebel, H.; Paquet, V.; Proulx, C. Angew. Chem. Int. Ed. 2001, 40, 2887.
74. (b) Grasa, G. A.; Moore, Z.; Martin, K. L.; Stevens, E. D.; Nolan, S. P.; Paquet, V.; Lebel, H. J. Organomet. Chem. 2002, 658, 126.
75. (c) Lebel, H.; Paquet, V. Org. Lett. 2002, 4, 1671.
76. (d) Lebel, H.; Guay, D.; Paquet, V.; Huard, K. Org. Lett. 2004, 6, 3047.
77. (e) Lebel, H.; Paquet, V. J. Am. Chem. Soc. 2004, 126, 320.
78. (f) Paquet, V.; Lebel, H. Synthesis 2005, 1901.
79. (a) Liao, Y.; Huang, Y. Z. Tetrahedron Lett. 1990, 31, 5897.
80. (b) Zhou, Z. L.; Huang, Y. Z.; Shi, L. L. Tetrahedron 1993, 49, 6821.
81. Lebel, H.; Davi, M.; Díez-González, S.; Nolan, S. P. J. Org. Chem. 2007, 72, 144.
82. As representative examples, the formation of the products given in Table 4, entries 1 and 4, was not observed when the reaction was carried out in the presence of copper(I) chloride instead of [(IPr)CuCl].
83. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 2004.
84. (a) Tornø, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
85. (b) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596.
86. (a) Huisgen, R. Pure Appl. Chem. 1989, 61, 613.
87. (b) Padwa, A. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M., Ed.; Pergamon: Oxford, 1991, 1069-1109.
88. (c) Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984, 1-176.
89. (a) Lutz, J.-F.; Börner, H. G.; Weichenhan, K. Macromol. Rapid Commun. 2005, 26, 514.
90. (b) Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853.
91. (c) Lewis, W. G.; Magallon, F. G.; Fokin, V. V.; Finn, M. G. J. Am. Chem. Soc. 2004, 126, 9152.
92. Pérez-Balderas, F.; Ortega-Muñoz, M.; Morales-Sanfrutos, J.; Hernández-Mateo, F.; Calvo-Flores, F. G.; Calvo-Asín, J. A.; Isac-García, J.; Santoyo-González, F. Org. Lett. 2003, 5, 1951.
93. Gerard, B.; Ryan, J.; Beeler, A. B.; Porco, J. A. Jr. Tetrahedron 2006, 62, 6405.
94. For previously reported systems, see: (a) Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; Van der Rycken, E. Org. Lett. 2004, 6, 4223.
95. (b) Feldman, A. K.; Colasson, B.; Fokin, V. V. Org. Lett. 2004, 6, 3897.
96. Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem. Int. Ed. 2005, 44, 2210; see also ref. 45a.
97. Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210.
98. Thompson, J. S.; Bradley, A. Z.; Park, K.-H.; Dobbs, K. D.; Marshall, W. Organometallics 2006, 25, 2712.
99. Nolte, C.; Mayer, P.; Straub, B. F. Angew. Chem. Int. Ed. 2007, 46, 2001.
100. (a) Tominaga, S.; Oi, Y.; Kato, T.; An, D. K.; Okamoto, S. Tetrahedron Lett. 2004, 45, 5585.
101. (b) Okamoto, S.; Tominaga, S.; Saino, N.; Kase, K.; Shimoda, K. J. Organomet. Chem. 2005, 690, 6001.
102. Larsen, A. O.; Leu, W.; Nieto Oberhuber, C.; Campbell, J. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 11130.
103. For selected examples, see: (a) Alexakis, A.; Winn, C. L.; Guillen, F.; Pytkowicz, J.; Roland, S.; Mangeney, P. Adv. Synth. Catal. 2003, 345, 345.
104. (b) Clavier, H.; Coutable, L.; Guillemin, J.-C.; Mauduit, M. Tetrahedron: Asymmetry 2005, 16, 921.
105. (c) Lee, K.-s.; Brown, M. K.; Hird, A. W.; Hoveyda, A. H. J. Am. Chem. Soc. 2006, 128, 7182.
106. (d) Martin, D.; Kehrli, S.; d'Augustin, M.; Clavier, H.; Mauduit, M.; Alexakis, A. J. Am. Chem. Soc. 2006, 128, 8416.
107. (e) Brown, M. K.; May, T. L.; Baxter, C. A.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2007, 46, 1097.
108. Munro-Leighton, C.; Blue, E. D.; Gunnoe, T. B. J. Am. Chem. Soc. 2006, 128, 1446.
109. [(IPr)CuCl] is now commercially available from Strem.