Copper(II) hydroxide complexes of N-heterocyclic carbenes and catalytic oxidative amination of arylboronic acids

Organometallics

Volumn 29, Issue 6, 2010, Pages 1457-1464

  Liu, Bo ^a   Liu, Bin ^a   Zhou, Yongbo ^a   Chen, Wanzhi ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINES; ARYLBORONIC ACIDS; CARBENE COMPLEXES; DINUCLEAR; ELEMENTAL ANALYSIS; IMIDAZOLIUM SALT; N-ARYLATION REACTIONS; N-HETEROCYCLIC CARBENES; PYRAZOLATE; PYRAZOLES; ROOM TEMPERATURE;

ACIDS; AMINATION; AMINES; AROMATIC COMPOUNDS; CARBON INORGANIC COMPOUNDS; CHEMICAL ANALYSIS; COPPER; COPPER POWDER; METHANOL; SILVER; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

COPPER COMPOUNDS;

EID: 77949476225     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100009u     Document Type: Article

References (47)

1. Garrison, J. C.; Youngs, W. J. Chem. Rev. 2005, 105, 3978.
2. Lin, I. J. B.; Vasam, C. S. Coord. Chem. Rev. 2007, 251, 642.
3. Lin, J. C. Y.; Huang, R. T. W.; Lee, C. S.; Bhattacharyya, A.; Hwang, W. S.; Lin, I. J. B. Chem. Rev. 2009, 109, 3561.
4. (a) Yun, J.; Kim, D.; Yun, H. Chem. Commun. 2005, 5181.
5. (b) Díez-González, S.; Kaur, H.; Zinn, F. K.; Stevens, E. D.; Nolan, S. P. J. Org. Chem. 2005, 70, 4784.
6. (a) Brown, M. K.; May. T. L.; Baxter, C. A.; Hoveyda, A. H. Angew. Chem.. Int. Ed. 2007, 46, 1097.
7. (b) Matsumoto, Y.; Yamada, K.; Tomioka, K. J. Org. Chem. 2008, 73, 4578.
8. (a) Van Veldhuizen, J. J.; Campbell, J. E.; Giudici, R. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 6877.
9. (b) Seo, H.; HirschWeil, D.; Abboud, K. A.; Hong, S. J. Org. Chem. 2008, 73, 1983.
10. (a) Fructos, M. R.; Belderrain, T. R.; Nicasio, M. C.; Nolan, S. P.; Kaur, H.; Díaz-Requeio, M. M.; Pérez, P. J. J. Am. Chem. Soc. 2004, 126, 10846.
11. (b) Fructos, M. R.; de Frémont, P.; Nolan, S. P.; Díaz-Requejo, M. M.; Pérez, P. J. Organometallics 2006, 25, 2237.
12. Lee, Y.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 3160.
13. (a) Hu, X.; Castro-Rodriguez, I.; Meyer, K. Orgnometallics 2003, 22, 3016.
14. (b) Gischig, S.; Togni, A. Organometallics 2005, 24, 203.
15. (c) Diez-Gonzalez, S.; Stevens, E. D.; Scott, N. M.; Petersen, J. L.; Nolan, S. P. Chem. Eur. J. 2008, 14, 158.
16. (d) Goj, L. A.; Blue, E. D.; Delp, S. A.; Gunnoe, T. B.; Cundari, T. R.; Petersen, J. L. Organometallics 2006, 25, 4097.
17. (a) Wylie, W. N. O.; Lough, A. J.; Morris, R. H. Organometallics 2010, 29, 570.
18. (b) Lee, C.-S.; Sabiah, S.; Wang, J.-C.; Hwang, W.-S.; Lin, I, J. B. Organometallics 2010, 29, 286.
19. (c) Zhang, X.; Qiu, Y.; Rao, B.; Luo, M. Organometallics 2009, 28, 3093.
20. (d) Ray, L.; Shaikh, M. M.; Ghosh, P. Inorg. Chem. 2008, 47, 230.
21. (a) Zhou, Y.; Chen, W. Organometallics 2007, 26, 2742.
22. (b) Liu, B.; Chen, W.; Jin, S. Organometallics 2007, 26, 3660.
23. (c) Zhou, Y.; Zhang, X.; Chen, W.; Qiu, H. J. Organomet. Chem. 2008, 693, 205.
24. Liu, B.; Xia, Q.; Chen, W. Angew. Chem.. Int. Ed. 2009, 48, 5513.
25. Zhou, Y.; Xi, Z.; Chen, W.; Wang, D. Organometallics 2008, 27, 5911.
26. Tulloch, A. A. D.; Danopoulos, A. A.; Kleinhenz, S.; Light, M. E.; Hursthouse, M. B.; Eastham, G. Organometallics 2001, 20, 2027.
27. (a) Arduengo, A. J. III; Rasika Dias, H. V.; Calabrese, J. C.; Davidson, F. Organometallics 1993, 12, 3405.
28. (b) Goj, L. A.; Blue, E. D.; Delp, S. A.; Gunnoe, T. B.; Cundari, T. R.; Pierpont, A. W.; Petersen, J. L.; Boyle, P. D. Inorg. Chem. 2006, 45, 9032.
29. (c) Mankad, N. P.; Laitar, D. S.; sadighi, J. P. Organometallics 2004, 23, 3369.
30. Chandrasekhar, V.; Senapati, T.; Saňudo, E. C. Inorg. Chem. 2008, 47, 9553.
31. Paital, A. R.; Nanda, P. K.; Das, S.; Aromí, G.; Ray, D. Inorg. Chem. 2006, 45, 505.
32. Arnold, P. L.; Rodden, M.; Davis, K. M.; Scarisbrick, A. C.; Blake, A. J.; Wilson, C. Chem. Commun. 2004, 1612.
33. Zhu, L.; Quo, P.; Li, G.; Lan, j.; Xie, R.; You, J. J. Org. Chem. 2007, 72, 8535.
34. (a) Ley, S. V.; Thomas, A. W. Angew. Chem.. Int. Ed. 2003, 42, 5400.
35. (b) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
36. (c) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
37. Chan, D. M. T.; Monaco, K. L.; Wang, R. P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933.
38. (a) Collman, J. P.; Zhong, M. Org., Lett. 2000, 2, 1233.
39. (b) Collman, J. P.; Zhong, M.; Zhang, C.; Costanzo, S. J. Org. Chem. 2001, 66, 7892.
40. (c) Antilla, J. C.; Buchwald, S. L. Org. Lett. 2001, 3, 2077.
41. (d) Lan, J.; Chen, L.; Yu, X.; You, J.; Xie, R. Chem. Commun. 2004, 188.
42. (a) Kantam, M. L.; Venkanna, G. T.; Sridhar, C.; Sreedhar, B.; Choudary, B. M. J. Org. Chem. 2006, 71, 9522.
43. (b) Chen, S.; Huang, H.; Liu, X.; Shen, J.; Jiang, H.; Liu, H. J. Comb. Chem. 2008, 10, 358.
44. (c) Singh, B. K.; Stevens, C. V.; Acke, D. R. J.; Parmar, V. S.; Van der Eycken, E. V. Tetrahedron Lett. 2009, 50, 15.
45. SMART-CCD Software, version 4.05; Siemens Analytical X-ray Instruments, Madison, WI, 1996.
46. Sheldrick, G. M., SHELXS-97 and SHELXL-97, Program for X-ray Crystal Structure Refinement; University of Göttingen, Göttingen, Germany, 1997.
47. Spek, A. L. PLATON, A Multipurpose Crystallographic Tool; University of Utrecht, Utrecht, The Netherlands, 1998.