Palladium-catalyzed oxidative C-H bond acylation of N-nitrosoanilines with toluene derivatives: A traceless approach to synthesize N-alkyl-2-aminobenzophenones

Chemical Communications

Volumn 50, Issue 97, 2014, Pages 15352-15354

  Wu, Yinuo ^a   Feng, Ling Jun ^a   Lu, Xiao ^a   Yee Kwong, Fuk ^b   Luo, Hai Bin ^a  

^a SUN YAT SEN UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; BENZOPHENONE DERIVATIVE; N ALKYL 2 AMINOBENZOPHENONE DERIVATIVE; N NITROSOANILINE DERIVATIVE; PALLADIUM; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG; TOLUENE;

ACYLATION; ALKYNYLATION; ARTICLE; CATALYSIS; CATALYST; COVALENT BOND; CROSS COUPLING REACTION; ELECTROPHILICITY; FRIEDEL CRAFTS REACTION; HIGH TEMPERATURE; OXIDATIVE COUPLING; STEREOSPECIFICITY; SYNTHESIS; CHEMISTRY; OXIDATION REDUCTION REACTION;

ACYLATION; ANILINE COMPOUNDS; BENZOPHENONES; CATALYSIS; OXIDATION-REDUCTION; PALLADIUM; TOLUENE;

EID: 84911388714     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc07440h     Document Type: Article

References (58)

1. G.Dyker, Handbook of C-H Transformations, Wiley-VCH, Weinheim, 2005
2. M. P.Doyle, K. I.Goldberg, Acc. Chem. Res., 2012:45, 777
3. K. M.Engle, T.-S.Mei, M.Wasa, J.-Q.Yu, Acc. Chem. Res., 2012:45, 788
4. S. R.Neufeldt, M. S.Sanford, Acc. Chem. Res., 2012:45, 936
5. C.-L.Sun, B.-J.Li, Z.-J.Shi, Chem. Rev., 2011:111, 1293
6. F.Bellina, R.Rossi, Chem. Rev., 2010:110, 1082
7. I. A. I.Mkhalid, J. H.Barnard, T. B.Marder, J. M.Murphy, J. F.Hartwig, Chem. Rev., 2010:110, 890
8. T. W.Lysons, M. S.Sanford, Chem. Rev., 2010:110, 1147
9. O.Daugulis, H.-Q.Do, D.Shabashov, Acc. Chem. Res., 2009:42, 1074
10. X.Chen, K. M.Engle, D.-H.Wang, J.-Q.Yu, Angew. Chem., Int. Ed., 2009:48, 5094
11. Y.Wu, J.Wang, F.Mao, F. Y.Kwong, Chem. - Asian J., 2014:9, 26
12. B.Liu, Y.Fan, Y.Gao, C.Sun, C.Xu, J.Zhu, J.Am. Chem. Soc., 2013:135, 468
13. C.Wang, Y.Huang, Org. Lett., 2013:15, 5294
14. X.Huang, J.Huang, C.Du, X.Zhang, F.Song, J.You, Angew. Chem., Int. Ed., 2013:52, 12970
15. D. J. C.Constable, P. J.Dunn, J. D.Hayler, G. R.Humphrey, J. L.Leazer, R. J.Linderman, L.Lorenz, J.Manley, B. A.Pearlman, A.Wells, A.Zaks, T. Y.Zhang, Green Chem., 2007:9, 411
16. H.Ogita, Y.Isobe, H.Takaku, R.Sekine, Y.Goto, S.Misawa, H.Hayashi, Bioorg. Med. Chem., 2002:10, 3473
17. K.Hirai, T.Fujishita, T.Ishiba, H.Sugimoto, S.Matsutani, Y.Tsukinoki, K.Hirose, J. Med. Chem., 1982:25, 1466
18. K.Hirai, T.Ishiba, H.Sugimoto, K.Sasakura, T.Fujishita, T.Toyoda, Y.Tsukinoki, H.Joyama, H.Hatakeyama, K.Hirose, J. Med. Chem., 1980:23, 764
19. J.Lee, S. J.Kim, H.Choi, Y. H.Kim, I. T.Lim, H. M.Yang, C. S.Lee, H. R.Kang, S. K.Ahn, S. K.Moon, D. H.Kim, S.Lee, N. S.Choi, K. J.Lee, J. Med. Chem., 2010:53, 6337
20. S.Singh, N. R.Prasad, E. E.Chufan, B. A.Patel, Y. J.Wang, Z. S.Chen, S. V.Ambudkar, T. T.Talele, J. Med. Chem., 2014:57, 4058
21. P. C.Huang, K.Parthasarathy, C. H.Cheng, Chem. - Eur. J., 2013:19, 460
22. A.Gerpe, G.Aguirre, L.Boiani, H.Cerecetto, M.Gonzalez, C.Olea-Azar, C.Rigol, J. D.Maya, A.Morello, O. E.Piro, V. J.Aran, A.Azqueta, A. L.de Cerain, A.Monge, M. A.Rojas, G.Yaluff, Bioorg. Med. Chem., 2006:14, 3467
23. D.Susanti, L. L. R.Ng, P. W. H.Chan, Adv. Synth. Catal.,2014:356, 353
24. G. A.Olah, Friedel-Crafts Chemistry, Wiley, New York, 1973
25. G.Sartori, R.Maggi, Chem. Rev., 2006:106, 1077
26. G.Sartori and R.Maggi, Advances in Friedel-Crafts Acylation Reactions, CRC Press, Boca Raton, FL, 2010
27. K.Prasad, G. L.Lee, A.Chaudhary, M. J.Girgis, J. W.Streemke, O.Repic, Org. Process Res. Dev., 2003:7, 723
28. C.Pan, X.Jia, J. Cheng, Synthesis, 2012, 677
29. C.Liu, H.Zhang, W.Shi, A.Lei, Chem. Rev., 2011:111, 1780
30. D. R.Stuart, K.Fagnou, Science, 2007:316, 1172
31. C. S.Yeung, V. M.Dong, Chem. Rev., 2011:111, 1215
32. P.Fang, M.Li, H.Ge, J.Am. Chem. Soc., 2010:132, 11898
33. Y.Wu, B.Li, F.Mao, X.Li, F. Y.Kwong, Org. Lett., 2011:13, 3258
34. C.Li, L.Wang, P.Li, W.Zhou, Chem. - Eur. J., 2011:17, 10208
35. C.-W.Chan, Z.Zhou, W. Y.Yu, Adv. Synth.Catal.,2011:353, 2999
36. P.Alvarez-Bercedo, A.Flores-Gaspar, A.Correa, R.Martin, J.Am. Chem. Soc., 2010:132, 466
37. Y.Yuan, D.Chen, X.Wang, Adv. Synth. Catal.,2011:353, 3373
38. Y.Wu, P. Y.Choy, F.Mao, F. Y.Kwong, Chem. Commun., 2013:49, 689
39. Z.Yin, P.Sun, J. Org. Chem., 2012:77, 11339
40. J.Weng, Z.Yu, X.Liu, G.Zhang, Tetrahedron Lett., 2013:54, 1205
41. S.Guin, K.Rout, A.Banerjee, S.Nandi, B. K.Patel, Org. Lett., 2012:14, 5294
42. T.Morimoto, K.Fuji, K.Tsutsumi, K.Kakiuchi, J.Am. Chem. Soc., 2002:124, 3806
43. A. de Meijere, in Metal-Catalyzed Cross-Coupling Reactions, ed. A. de Meijere and F. Diederich, Wiley-VCH, Weinheim, 2nd edn, 2004, vol. 1-2
44. Handbook of Organopalladium for Organic Synthesis, ed. E.-I. Negishi, Wiley-Interscience, 2002, vol. 1-2
45. J.Tsuji, PalladiumReagents and Catalysts, Wiley, Chichester, 2nd edn, 2004
46. C.Wurtele, O.Sander, V.Lutz, T.Waitz, F.Tuczek, S.Schindler, J.Am. Chem. Soc., 2009:131, 7544
47. H. R.Lucas, L.Li, A. A. N.Sarjeant, M. A.Vance, E. I.Solomon, K. D.Karlin, J.Am. Chem. Soc., 2009:131, 3230
48. T. G.Carrell, S.Cohen, G. C.Dismukes, J.Mol. Catal. A: Chem., 2002:187, 3
49. A. J.Catino, J. M.Nichols, H.Choi, S.Gottipamula, M. P.Doyle, Org. Lett., 2005:7, 5167
50. E. C.McLaughlin, H.Choi, K.Wang, G.Chiou, M. P.Doyle, J. Org. Chem., 2009:74, 730
51. C.Chatgilialoglu, D.Crich, M.Komatsu, I.Ryu, Chem. Rev., 1999:99, 1991
52. F. A.Chavez, P. K.Mascharak, Acc. Chem. Res., 2000:33, 539
53. N. R.Deprez, M. S.Sanford, J.Am. Chem. Soc., 2009:131, 11234
54. J. M.Racowski, A. R.Dick, M. S.Sanford, J.Am. Chem. Soc., 2009:131, 10974
55. D. C.Powers, T.Ritter, Acc. Chem. Res., 2012:45, 840
56. D. C.Powers, T.Ritter, Nat. Chem., 2009:1, 302
57. D. C.Powers, M. A. L.Geibel, J. E. M. N.Klein, T.Ritter, J.Am. Chem. Soc. 2009:131, 17050
58. J. J.Warren, J. M.Mayer, J.Am. Chem. Soc., 2010:132, 7784