Direct oxidative arylation of aryl C-H bonds with aryl boronic acids via pd catalysis directed by the N,N-dimethylaminomethyl group

Chemistry - An Asian Journal

Volumn 10, Issue 4, 2015, Pages 840-843

  Zhang, Ji Cheng ^a,b   Shi, Jiang Ling ^c   Wang, Bi Qin ^c   Hu, Ping ^c   Zhao, Ke Qing ^c   Shi, Zhang Jie ^a,d  

^a PEKING UNIVERSITY   (China)

^b Peking University   (China)

^c SICHUAN NORMAL UNIVERSITY   (China)

^d INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

biaryls; boronic acid; C H activation; N,N dimethylbenzylamine; oxidative coupling

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; CHEMICAL REACTIONS;

BIARYLS; BORONIC ACID; C-H ACTIVATION; EFFICIENT COUPLING; OXIDATIVE ARYLATION; OXIDATIVE COUPLINGS; PALLADIUM-CATALYZED; VARIOUS SUBSTRATES;

AROMATIC COMPOUNDS;

BORONIC ACID DERIVATIVE; HYDROCARBON; PALLADIUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HYDROGEN BOND; OXIDATION REDUCTION REACTION;

BORONIC ACIDS; CATALYSIS; HYDROCARBONS; HYDROGEN BONDING; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PALLADIUM;

EID: 84925393727     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201403292     Document Type: Article

References (65)

1. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457
2. N. Miyaura, J. Organomet. Chem. 2002, 653, 54
3. N. Miyaura, Top. Curr. Chem. 2002, 219, 11
4. A. Suzuki, J. Organomet. Chem. 1999, 576, 147
5. N. Miyaura, T. Ishiyama, M. Ishikawa, A. Suzuki, Tetrahedron Lett. 1986, 27, 6369
6. S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. Int. Ed. 2001, 40, 4544
7. Angew. Chem. 2001, 113, 4676
8. K. C. Nicolaou, G. E. A. Carenzi, V. Jeso, Angew. Chem. Int. Ed. 2005, 44, 3895
9. Angew. Chem. 2005, 117, 3963.
10. S. H. Cho, J. Y. Kim, J. Kwak, S. Chang, Chem. Soc. Rev. 2011, 40, 5068
11. J. Wencel-Delord, T. Drçge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740
12. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
13. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788
14. J. Yamaguchi, A. D. Yamaguchi, K. Itami, Angew. Chem. 2012, 124, 9092
15. J. Wencel-Delord, F. Glorius, Nat. Chem. 2013, 5, 369.
16. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359
17. G. Bringmann, A. J. Price Mortimer, P. A. Keller, M. J. Gresser, J. Garner, M. Breuning, Angew. Chem. Int. Ed. 2005, 44, 5384
18. Angew. Chem. 2005, 117, 5518
19. J. P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651
20. A. C. Grimsdale, K. L. Chan, R. E. Martin, P. G. Jokisz, A. B. Holmes, Chem. Rev. 2009, 109, 897.
21. J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527
22. O. Daugulis, H. Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074
23. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879.
24. M. Wasa, B. T. Worrell, J.-Q. Yu, Angew. Chem. Int. Ed. 2010, 49, 1275
25. Angew. Chem. 2010, 122, 1297.
26. D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330-7331
27. Z.-Q. Lei, H. Li, Y. Li, X.-S. Zhang, K. Chen, X. Wang, J. Sun, Z.-J. Shi, Angew. Chem. Int. Ed. 2012, 51, 2690-2694
28. Angew. Chem. 2012, 124, 2744-2748.
29. O. Daugulis, V. G. Zaitsev, Angew. Chem. Int. Ed. 2005, 44, 4046
30. Angew. Chem. 2005, 117, 4114.
31. S.-D. Yang, B.-J. Li, X.-B. Wan, Z.-J. Shi, J. Am. Chem. Soc. 2007, 129, 6066
32. B.-J. Li, S.-L. Tian, Z. Fang, Z.-J. Shi, Angew. Chem. Int. Ed. 2008, 47, 1115
33. Angew. Chem. 2008, 120, 1131
34. D.-D. Li, T.-T. Yuan, G.-W. Wang, J. Org. Chem. 2012, 77, 3341
35. F. Péron, C. Fossey, T. Cailly, F. Fabis, Org. Lett. 2012, 14, 1827.
36. N. Yoshikai, A. Matsumoto, J. Norinder, E. Nakamura, Angew. Chem. Int. Ed. 2009, 48, 2925
37. Angew. Chem. 2009, 121, 2969
38. M. J. Tredwell, M. Gulias, N. G. Bremeyer, C. C. C. Johansson, B. S. L. Collins, M. J. Gaunt, Angew. Chem. Int. Ed. 2011, 50, 1076
39. Angew. Chem. 2011, 123, 1108.
40. T. Vogler, A. Studer, Org. Lett. 2008, 10, 129-131
41. H. Li, W. Wei, Y. Xu, C. Zhang, X.-B. Wan, Chem. Commun. 2011, 47, 1497.
42. A. Lazareva, O. Daugulis, Org. Lett. 2006, 8, 5211.
43. H. A. Chiong, Q.-N. Pham, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 9879
44. R. Giri, N. Maugel, J.-J. Li, D.-H. Wang, S. P. Breazzano, L. B. Saunders, J.-Q. Yu, J. Am. Chem. Soc. 2007, 129, 3510
45. D.-H. Wang, T.-S. Mei, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 17676
46. K. M. Engle, P. S. Thuy-Boun, M. Dang, J.-Q. Yu, J. Am. Chem. Soc. 2011, 133, 18183.
47. W. T. Caldwell, T. R. Thompson, J. Am. Chem. Soc. 1939, 61, 765
48. A. McCoubrey, J. Chem. Soc. 1951, 2931
49. H. Dahn, P. Zoller, Helv. Chim. Acta 1952, 35, 1348
50. D. Beke, L. Toke, Chem. Ber. 1962, 95, 2122
51. W. E. Solodar, M. Green, J. Org. Chem. 1962, 27, 1077
52. H. Dahn, J. A. Garbarino, C. O. Murchu, Helv. Chim. Acta 1970, 53, 1370.
53. A. Cecchetto, F. Minisci, F. Recupero, F. Fontana, G. F. Pedulli, Tetrahedron Lett. 2002, 43, 3605
54. E. Baciocchi, T. D. Giacco, A. Lapi, Org. Lett. 2004, 6, 4791.
55. C. R. Sanders II, J. H. Prestegard, J. Am. Chem. Soc. 1991, 113, 1987.
56. F. Kakiuchi, K. Igi, M. Matsumoto, T. Hayamizu, N. Chatani, S. Murai, Chem. Lett. 2002, 396.
57. A. J. Roering, L. V. A. Hale, P. A. Squier, M. A. Ringgold, E. R. Wiederspan, T. B. Clark, Org. Lett. 2012, 14, 3558.
58. G.-X. Cai, Y. Fu, Y.-Z. Li, X.-B. Wan, Z.-J. Shi, J. Am. Chem. Soc. 2007, 129, 7666.
59. H. Li, G.-X. Cai, Z.-J. Shi, Dalton Trans. 2010, 39, 10442.
60. C. Pi, Y. Li, X.-L. Cui, H. Zhang, Y.-B. Han, Y.-J. Wu, Chem. Sci. 2013, 4, 2675.
61. C. Pi, X.-L. Cui, X.-Y. Liu, M.-X. Guo, H.-Y. Zhang, Y.-J. Wu, Org. Lett. 2014, 16, 5164.
62. H. Zhang, X.-L. Cui, X.-N. Yao, H. Wang, J.-Y. Zhang, Y.-J. Wu, Org. Lett. 2012, 14, 3012.
63. D.-W. Gao, Y.-C. Shi, Q. Gu, Z.-L. Zhao, S.-L. You, J. Am. Chem. Soc. 2013, 135, 86.
64. R.-K. Feng, J.-Z. Yao, Z.-J. Liang, Z.-X. Liu, Y.-H. Zhang, J. Org. Chem. 2013, 78, 3688.
65. S. Bhattacharyya, J. Org. Chem. 1995, 60, 4928.