Palladium-catalyzed oxidative ortho-acylation of 2-arylbenzoxazoles and 2-arylbenzothiazoles with toluene derivatives

Tetrahedron

Volumn 71, Issue 10, 2015, Pages 1574-1580

  Zheng, Yong ^a   Song, Wei Bin ^a   Zhang, Shu Wei ^a   Xuan, Li Jiang ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

2 Arylbenzothiazole; 2 Arylbenzoxazole; Acylation; Palladium

Indexed keywords

2 (2 BENZOYL 4 METHOXYPHENYL)BENZOXAZOLE; 2 (2 BENZOYL 4 METHYLPHENYL)BENZOXAZOLE; 2 (2 BENZOYL 5 METHYLPHENYL)BENZOXAZOLE; 2 (2 BENZOYL 6 CHLOROPHENYL)BENZOXAZOLE; 2 (2 BENZOYL 6 FLUOROPHENYL)BENZOXAZOLE; 2 (2 BENZOYL PHENYL)BENZOTHIAZOLE; 2 (2 BENZOYL PHENYL)BENZOXAZOLE; 2 (2 BENZOYLPHENYL) 5 CHLOROBENZOXAZOLE; 2 ARYLBENZOTHIAZOLE DERIVATIVE; 2 ARYLBENZOXAZOLE DERIVATIVE; 2 [2 (2 CHLOROBENZOYL) PHENYL]BENZOXAZOLE; 2 [2 (2 CHOLROBENZOYL) PHENYL]BENZOTHIAZOLE; 2 [2 (2 METHYLBENZOYL) PHENYL]BENZOXAZOLE; 2 [2 (3 METHYLBENZOYL) PHENYL]BENZOTHIAZOLE; 2 [2 (3 METHYLBENZOYL) PHENYL]BENZOXAZOLE; 2 [2 (3,5 DIMETHYLBENZOYL) PHENYL]BENZOTHIAZOLE; 2 [2 (3,5 DIMETHYLBENZOYL) PHENYL]BENZOXAZOLE; 2 [2 (4 BROMOBENZOYL) PHENYL]BENZOXAZOLE; 2 [2 (4 CHLOROBENZOYL) PHENYL]BENZOXAZOLE; 2 [2 (4 METHOXYBENZOYL) PHENYL]BENZOTHIAZOLE; 2 [2 (4 METHOXYBENZOYL) PHENYL]BENZOXAZOLE; 2 [2 (4 METHYLBENZOYL) PHENYL]BENZOTHIAZOLE; 2 [2 (4 METHYLBENZOYL) PHENYL]BENZOXAZOLE; ALCOHOL DERIVATIVE; ALDEHYDE; BENZOTHIAZOLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; PALLADIUM; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACYLATION; ARTICLE; CATALYST; DRUG MECHANISM; ELECTRON; METHODOLOGY; OXIDATION; PRIORITY JOURNAL; STEREOSPECIFICITY;

EID: 84923069214     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.01.025     Document Type: Article

References (73)

1. Y. Deng, Y.W. Chin, H. Chai, Y.J. Keller, and A.D. Kinghorn J. Nat. Prod. 70 2007 2049
2. K.R. Romines, G.A. Freeman, L.T. Schaller, J.R. Coman, S.S. Gonzales, J.H. Tidwell, C.W. Andrews, D.K. Stammers, R.J. Hazen, R.G. Ferris, S.A. Short, J.H. Chan, and L.R. Boone J. Med. Chem. 49 2006 727
3. G. Sartori, and R. Maggi Advances in Friedel-Crafts Acylation Reactions 2010 CRC FL
4. G.A. Olah Friedel-Crafts Chemistry 1973 Wiley New York, NY for mild and improved Friedel-Crafts Acylation, see
5. C.O. Kangani, and B.W. Day Org. Lett. 10 2008 2645
6. M.H. Sarvari, and H. Sharghi Synthesis 2004 2165
7. M.C. Wilkinson Org. Lett. 13 2011 2232
8. F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, and S. Murai Bull. Chem. Soc. Jpn. 68 1995 62
9. O. Daugulis, H.-Q. Do, and D. Shabashov Acc. Chem. Res. 42 2009 1074
10. X. Chen, K.M. Engle, D.-H. Wang, and J.-Q. Yu Angew. Chem., Int. Ed. 48 2009 5094
11. R. Giri, B.-F. Shi, K.M. Engle, N. Maugel, and J.-Q. Yu Chem. Soc. Rev. 38 2009 3242
12. T.W. Lyons, and M.S. Sanford Chem. Rev. 110 2010 1147
13. D.A. Colby, R.G. Bergman, and J.A. Ellman Chem. Rev. 110 2010 624
14. J. Wencel-Delord, T. Dröge, F. Liu, and F. Glorius Chem. Soc. Rev. 40 2011 4740
15. P.B. Arockiam, C. Bruneau, and P.H. Dixneuf Chem. Rev. 112 2012 5879
16. L. Ackermann Acc. Chem. Res. 47 2014 281
17. C.S. Yeung, and V.M. Dong Chem. Rev. 111 2011 1215
18. K.J. Fraunhoffer, and M.C. White J. Am. Chem. Soc. 129 2007 7274
19. D.J. Covell, N.A. Vermeulen, N.A. Labenz, and M.C. White Angew. Chem., Int. Ed. 45 2006 8217
20. J.H. Delcamp, and M.C. White J. Am. Chem. Soc. 128 2006 15076
21. D.R. Stuart, and K. Fagnou Science 316 2007 1172
22. M. Lafrance, and K. Fagnou J. Am. Chem. Soc. 128 2006 16496
23. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174
24. E.M. Beccalli, G. Broggini, M. Martinelli, and S. Sottocornola Chem. Rev. 107 2007 5318
25. J.D. Neukom, A.S. Aquino, and J.P. Wolfe Org. Lett. 13 2011 2196
26. D. Kim, and S. Hong Org. Lett. 13 2011 4466
27. S.R. Neufeldt, and M.S. Sanford Acc. Chem. Res. 45 2012 936
28. X. Jia, S. Zhang, W. Wang, F. Luo, and J. Cheng Org. Lett. 11 2009 3210
29. F. Xiao, Q. Shuai, F. Zhao, G. Deng, and C.-J. Li Org. Lett. 13 2011 1614
30. S. Guin, S.K. Rout, A. Banerjee, S. Nandi, and B.K. Patel Org. Lett. 14 2012 5294
31. Y. Wu, B. Li, F. Mao, X. Li, and F.Y. Kwong Org. Lett. 13 2011 3258
32. C. Li, L. Wang, P. Li, and W. Zhou Chem. - Eur. J. 17 2011 10208
33. C.-W. Chan, Z. Zhou, and W.Y. Yu Adv. Synth. Catal. 353 2011 2999
34. Y. Yuan, D. Chen, and X. Wang Adv. Synth. Catal. 353 2011 3373
35. Y. Wu, P.Y. Choi, F. Mao, and F.Y. Kwong Chem. Commun. 2013 689
36. P. Fang, M. Li, and H. Ge J. Am. Chem. Soc. 132 2010 11898
37. Z. Yin, and P. Sun J. Org. Chem. 77 2012 11339
38. J. Weng, Z. Yu, X. Liu, and G. Zhang Tetrahedron Lett. 54 2013 1205
39. S. Sharma, M. Kim, J. Park, M. Kim, J.H. Kwak, Y.H. Jung, J.S. Oh, Y. Lee, and I.S. Kim Eur. J. Org. Chem. 2013 6656
40. S. Han, S. Sharma, J. Park, M. Kim, Y. Shin, N.K. Mishra, J.J. Bae, J.W. Kwak, Y.H. Jung, and I.S. Kim J. Org. Chem. 79 2014 275
41. F. Xiong, C. Qian, D. Lin, W. Zeng, and X. Lu Org. Lett. 15 2013 5444
42. H. Li, P. Li, and L. Wang Org. Lett. 15 2013 620
43. H. Song, D. Chen, C. Pi, X. Cui, and Y. Wu J. Org. Chem. 79 2014 2955
44. Y.-N. Ma, Q.-P. Tian, H.-Y. Zhang, A.-X. Zhou, and S.-D. Yang Org. Chem. Front. 1 2014 284
45. Z. Jin Nat. Prod. Rep. 28 2011 1143
46. S.M. Rida, F.A. Ashour, S.A.M. El-Hawash, M.M. ElSemary, M.H. Badr, and M.A. Shalaby Eur. J. Med. Chem. 40 2005 949
47. S.M. Sondhi, N. Singh, A. Kumar, O. Lozach, and L. Meijer Bioorg. Med. Chem. 14 2006 3758
48. L.K. Mangion, B.D. Sherry, J.-J. Yin, and F. Fleitz J. Org. Lett. 14 2012 3458
49. A.D. Rodríguez, C. Ramírez, I.I. Rodríguez, and E. Gonzalez Org. Lett. 1 1999 527
50. S. Noël, S. Cadet, E. Gras, and C. Hureau Chem. Soc. Rev. 42 2013 7747
51. C.G. Mortimer, G. Wells, J.-P. Crochard, E.L. Stone, T.D. Bradshaw, M.F.G. Stevens, and A.D. Westwell J. Med. Chem. 49 2006 179
52. K. Serdons, C. Terwinghe, P. Vermaelen, K. Van Laere, H. Kung, L. Mortelmans, G. Bormans, and A. Verbruggen J. Med. Chem. 52 2009 1428
53. C. Rodríguez-Rodríguez, N.S.D. Groot, A. Rimola, A. Alvarez-Larena, V. Lloveras, J. Vidal-Gancedo, S. Ventura, J. Vendrell, M. Sodupe, and P. Gonzalez-Duarte J. Am. Chem. Soc. 131 2009 1436
54. P.S. Yadav, Devprakash, and G.P. Senthilkumar Int. J. Pharm. Sci. Drug Res. 1 2011 01
55. H. Kai, Y. Morioka, Y. Koriyama, K. Okamoto, Y. Hasegawa, M. Hattori, K. Koike, H. Chiba, S. Shinohara, Y. Iwamoto, K. Takahashi, and N. Tanimoto Bioorg. Med. Chem. Lett. 18 2008 6444
56. I. Takehiro, K. Satoko, and S. Hiroaki Jpn. Kokai Tokkyo Koho Feb 03 2011 JP 2011021010 A
57. Q. Zhang, C. Li, F. Yang, J. Li, and Y. Wu Tetrahedron 69 2013 320
58. A. Banerjee, S.K. Santra, S. Guin, S.K. Rout, and B.K. Patel Eur. J. Org. Chem. 2013 1367
59. Q. Zhang, F. Yang, and Y. Wu Tetrahedron 69 2013 4908
60. Q. Ding, F. Ji, C. Ye, J. Wang, J. Wang, L. Zhou, and Y. Peng Tetrahedron 69 2013 8661
61. J. Wang, Z. Nie, Y. Li, S. Tan, J. Jiang, P. Jiang, and Q. Ding J. Chem. Res. 37 2013 263
62. C. Chatgilialoglu, D. Crich, M. Komatsu, and I. Ryu Chem. Rev. 99 1999 1991 for recent selected examples of acyl radicals, see
63. Z. Liu, J. Zhang, S. Chen, E. Shi, Y. Xu, and X. Wan Angew. Chem., Int. Ed. 51 2012 3231
64. Z. Shi, and F. Glorius Chem. Sci. 4 2013 829
65. C.F. Rosewall, P.A. Sibbald, D.V. Liskin, and F.E. Michael J. Am. Chem. Soc. 131 2009 9488
66. N.R. Deprez, and M.S. Sanford J. Am. Chem. Soc. 131 2009 11234
67. J.M. Racowski, A.R. Dick, and M.S. Sanford J. Am. Chem. Soc. 131 2009 10974
68. S.R. Whitfield, and M.S. Sanford J. Am. Chem. Soc. 129 2007 15142
69. P.A. Sibbald, C.F. Rosewall, R.D. Swartz, and F.E. Michael J. Am. Chem. Soc. 131 2009 15945
70. D.C. Powers, M.A.L. Geibel, J.E.M.N. Klein, and T. Ritter J. Am. Chem. Soc. 131 2009 17050
71. F. Yang, Y. Wu, Z. Zhu, J. Zhang, and Y. Li Tetrahedron 64 2008 6782
72. J. Chang, K. Zhao, and S. Pan Tetrahedron Lett. 43 2002 951 for preparation of 2-arylbenzothiazoles, see
73. Z. Yang, X. Chen, S. Wang, J. Liu, K. Xie, A. Wang, and Z. Tan J. Org. Chem. 77 2012 7086