Catalytic C-H bond arylation of aryl imines and oxazolines in water with ruthenium(II)-acetate catalyst

Tetrahedron

Volumn 68, Issue 26, 2012, Pages 5179-5184

  Li, Bin ^a   Devaraj, Karthik ^a   Darcel, Christophe ^a   Dixneuf, Pierre H ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

C H activation functionalisation; Catalysis in water; Imine arylation; Oxazolines; Ruthenium acetate catalyst

Indexed keywords

ACETIC ACID; CARBON; HYDROGEN; IMINE; ORGANIC SOLVENT; OXAZOLINE DERIVATIVE; PHENYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RUTHENIUM DERIVATIVE; WATER;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 84861667823     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.117     Document Type: Article

References (120)

1. L. Ackermann Chem. Rev. 111 2011 1315
2. J. Choi, A.H.R. MacArthur, M. Brookhart, and A.S. Goldman Chem. Rev. 111 2011 1761
3. T.W. Lyons, and M.S. Sanford Chem. Rev. 110 2010 1147
4. D.A. Colby, R.G. Bergmann, and J.A. Ellman Chem. Rev. 110 2010 624
5. T. Satoh, and M. Miura Synthesis 2010 3395
6. C.J. Li Acc. Chem. Res. 42 2009 335
7. X. Chen, K.M. Engle, D.-H. Wang, and J.-Q. Yu Angew. Chem., Int. Ed. 48 2009 5094
8. I.V. Seregin, and V. Gevorgyan Chem. Soc. Rev. 36 2007 1173
9. L.C. Campeau, and K. Fagnou Chem. Commun. 2006 1253
10. F. Kakiuchi, and S. Murai Acc. Chem. Res. 35 2002 826
11. V. Ritleng, C. Sirlin, and M. Pfeffer Chem. Rev. 102 2002 1731
12. B. Join, T. Yamamoto, and K. Itami Angew. Chem., Int. Ed. 48 2009 3644
13. L.-C. Campeau, D.R. Stuart, J.-P. Leclerc, M. Bertrand-Laperle, E. Villemure, H.-Y. Sun, S. Lasserre, N. Guimond, M. Lecavallier, and K. Fagnou J. Am. Chem. Soc. 131 2009 3291
14. F. Yang, Y. Wu, Y. Li, B. Wang, and J. Zhang Tetrahedron 65 2009 914
15. C.C. Scarborough, R.I. McDonald, C. Hartmann, G.T. Sazama, A. Bergant, and S.S. Stahl J. Org. Chem. 74 2009 2613
16. J. Roger, F. Pozgan, and H. Doucet Adv. Synth. Catal. 352 2010 696
17. M. Yu, Z. Liang, Y. Wang, and Y. Zhang J. Org. Chem. 76 2011 4987
18. K.J. Stowers, K.C. Fortner, and M.S. Sanford J. Am. Chem. Soc. 133 2011 6541
19. D.-H. Wang, K.M. Engle, B.-F. Shi, and J.-Q. Yu Science 327 2010 315
20. K.M. Engle, D.-H. Wang, and J.-Q. Yu Angew. Chem., Int. Ed. 49 2010 6169
21. H. Li, B.-J. Li, and Z.-J. Shi Catal. Sci. Technol. 1 2011 191
22. S. Murai, F. Kakiuchi, S. Sekini, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chatani Nature 366 1993 529
23. F. Kakiuchi, and N. Chatani C. Bruneau, P.H. Dixneuf, Topics in Organometallic Chemistry Vol. 11 2004 Springer Berlin 45
24. F. Kakiuchi, and N. Chatani Adv. Synth. Catal. 345 2003 1077
25. F. Kakiuchi, and T. Kochi Synthesis 2008 3013
26. S. Hiroshima, D. Matsumura, T. Kochi, and F. Kakiuchi Org. Lett. 12 2010 5318
27. R. Martinez, M.-O. Simon, R. Chevalier, C. Pautigny, J.-P. Genet, and S. Darses J. Am. Chem. Soc. 131 2009 7887 Ru(II)catalysts
28. S. Oi, S. Fukita, N. Hirata, N. Watanuki, S. Miyano, and Y. Inoue Org. Lett. 3 2001 2579
29. S. Oi, K. Sakai, and Y. Inoue Org. Lett. 7 2005 4009
30. L. Ackermann, A.V. Lygin, and N. Hofmann Angew. Chem., Int. Ed. 50 2011 6379
31. L. Ackermann, and J. Pospech Org. Lett. 13 2011 4153
32. L. Ackermann, R. Born, and R. Vicente ChemSusChem 2 2009 546
33. T. Kochi, S. Urano, H. Seki, E. Mizushima, M. Sato, and F. Kakiuchi J. Am. Chem. Soc. 131 2009 2792
34. T. Kochi, A. Tazawa, K. Honda, and F. Kakiuchi Chem. Lett. 40 2011 1018
35. T. Ueyama, S. Mochida, T. Fukutani, K. Hirano, T. Satoh, and M. Miura Org. Lett. 13 2011 706
36. I. Ozdemir, S. Demir, B. Cetinkaya, C. Gourlaouen, F. Maseras, C. Bruneau, and P.H. Dixneuf J. Am. Chem. Soc. 130 2008 1156
37. W. Li, P.B. Arockiam, C. Fischmeister, C. Bruneau, and P.H. Dixneuf Green. Chem. 13 2011 2315
38. P.B. Arockiam, C. Fischmeister, C. Bruneau, and P.H. Dixneuf Green. Chem. 13 2011 3075 Rhodium catalysts
39. C.-H. Jun, J.-B. Hong, Y.-H. Kim, and K.-Y. Chung Angew. Chem., Int. Ed. 39 2000 3440
40. G. Vo-Thanh, H. Lahrache, A. Loupy, I.-J. Kim, D.-H. Chang, and C.-H. Jun Tetrahedron 60 2004 5539
41. A.-S. Tsai, M. Brasse, R.G. Bergman, and J.A. Ellman Org. Lett. 13 2011 540
42. S. Rakshit, C. Grohmann, T. Besset, and F. Glorius J. Am. Chem. Soc. 133 2011 2350
43. M.P. Huestis, L. Chan, D.R. Stuart, and K. Fagnou Angew. Chem., Int. Ed. 50 2011 1338
44. T.K. Hyster, and T. Rovis J. Am. Chem. Soc. 132 2010 10565
45. T.-J. Gong, B. Xiao, Z.-J. Liu, J. Wan, J. Xu, D.-F. Luo, Y. Fu, and L. Liu Org. Lett. 13 2011 3235
46. S. Mochida, K. Hirano, T. Satoh, and M. Miura J. Org. Chem. 76 2011 3024
47. N. Guimond, C. Gouliaras, and K. Fagnou J. Am. Chem. Soc. 132 2010 6908
48. Y. Li, B.-J. Li, W.-H. Wang, W.-P. Huang, X.-S. Zhang, K. Chen, and Z.-J. Shi Angew. Chem., Int. Ed. 50 2011 2115
49. H. Li, Y. Li, X.-S. Zhang, K. Chen, X. Wang, and Z.-J. Shi J. Am. Chem. Soc. 133 2011 15244
50. F. Spindler, and H.-U. Blaser M. Beller, C. Bolm, 2nd ed. Transition Metals for Organic Synthesis Vol. 2 2004 Wiley-VCH Weinheim 113
51. H.-U. Blaser, and F. Spindler J.G. de Vries, C.J. Elsevier, Handbook of Homogeneous Hydrogenation Vol. 3 2007 Wiley-VCH Weinheim 1193
52. W. Tang, and X. Zhang Chem. Rev. 103 2003 3029
53. T.C. Nugent, and M. El-Shazly Adv. Synth. Catal. 352 2010 753
54. A. Fabrello, A. Bachelier, M. Urrutigoïty, and P. Kalck Coord. Chem. Rev. 254 2010 273
55. J.-H. Xie, S.-F. Zhu, and Q.-L. Zhou Chem. Rev. 111 2011 1713
56. K. Junge, K. Schröder, and M. Beller Chem. Commun. 2011 4849
57. J. Gajewy, J. Gawronski, and M. Kwit Org. Biomol. Chem. 9 2011 3863
58. V. Bette, A. Mortreux, D. Savoia, and J.-F. Carpentier Adv. Synth. Catal. 347 2005 289 Examples with Ti catalyst
59. H. Gruber-Woelfler, J.G. Khinast, M. Flock, R.C. Fischer, J. Sassmann-Shausen, T. Stanoeva, and G. Gescheidt Organometallics 28 2009 2546 Examples with Ir catalyst
60. L.D. Field, B.A. Messerle, and S.L. Rumble Eur. J. Org. Chem. 2005 2881 Cu catalyst
61. B.H. Lipshutz, and H. Shimizu Angew. Chem., Int. Ed. 43 2004 2227 Examples with Ru
62. Y. Nishibayashi, I. Takei, S. Uemura, and M. Hidai Organometallics 17 1998 3420
63. H. Hashimoto, I. Aratani, C. Kabuto, and M. Kira Organometallics 22 2003 2199
64. B. Li, J.-B. Sortais, C. Darcel, and P.H. Dixneuf ChemSusChem 5 2012 396 With Fe catalyst
65. L.C. Misal Castro, J.-B. Sortais, and C. Darcel Chem. Commun. 48 2012 151
66. B. Li, C.B. Bheeter, C. Darcel, and P.H. Dixneuf ACS Catal. 1 2011 1221
67. For a review see: C.S. Marques, and A.J. Burke ChemCatChem 3 2011 635
68. C.I. Herrerias, X. Yao, Z. Li, and C.-J. Li Chem. Rev. 107 2007 2546
69. C.-J. Li, and C. Wei Chem. Commun. 2002 268
70. C. Wei, and C.-J. Li J. Am. Chem. Soc. 124 2002 5638
71. C. Wei, and C.-J. Li J. Am. Chem. Soc. 125 2003 9584
72. C. Wei, Z. Li, and C.-J. Li Org. Lett. 5 2003 4473
73. B. Huang, X. Yao, and C.-J. Li Adv. Synth. Catal. 348 2006 1528
74. P.B. Alper, C. Meyers, A. Lerchner, D.R. Siegel, and E.M. Carreira Angew. Chem., Int. Ed. 38 1999 3186
75. D.E. Frantz, R. Fassler, and E.M. Carreira J. Am. Chem. Soc. 121 1999 11245
76. C. Koradin, K. Polborn, and P. Knochel Angew. Chem., Int. Ed. 41 2002 2535
77. V.S. Thirunavukkarasu, K. Parthasarathy, and C.-H. Cheng Angew. Chem., Int. Ed. 47 2008 9462
78. V.S. Thirunavukkarasu, K. Parthasarathy, and C.-H. Cheng Chem. - Eur. J. 16 2010 1436
79. J. Peng, T. Chen, C. Chen, and B. Li J. Org. Chem. 76 2011 9507
80. X.-X. Yan, Q. Peng, Y. Zhang, K. Zhang, W. Hong, X.-L. Hou, and Y.-D. Wu Angew. Chem., Int. Ed. 45 2006 1979
81. W. Zeng, G.-Y. Chen, Y.-G. Zhou, and Y.-X. Li J. Am. Chem. Soc. 129 2007 750
82. J.M. Longmire, B. Wang, and X. Zhang J. Am. Chem. Soc. 124 2002 13400
83. M.J. Tredwell, M. Gulias, N.G. Bremeyer, C.C.C. Johansson, B.S.L. Collins, and M.J. Gaunt Angew. Chem., Int. Ed. 50 2011 1076
84. H. Nakamura, K. Nakamura, and Y. Yamamoto J. Am. Chem. Soc. 120 1998 4242
85. K. Nakamura, H. Nakamura, and Y. Yamamoto J. Org. Chem. 64 1999 2614
86. R.A. Fernandes, A. Stimac, and Y. Yamamoto J. Am. Chem. Soc. 125 2003 14133
87. M. Kim, J. Kwak, and S. Chang Angew. Chem., Int. Ed. 48 2009 8935
88. K.-H. Ng, Z. Zhou, and W.-Y. Yu Org. Lett. 14 2012 272
89. K. Ueura, T. Satoh, and M. Miura Org. Lett. 7 2005 2229
90. C.-H. Jun, K.-Y. Chung, and J.-B. Hong Org. Lett. 3 2001 785
91. N. Yoshikai, A. Matsumoto, J. Norinder, and E. Nakamura Angew. Chem., Int. Ed. 48 2009 2925 Cobalt
92. K. Gao, and N. Yoshikai Angew. Chem., Int. Ed. 50 2011 6888
93. P.-S. Lee, T. Fujita, and N. Yoshikai J. Am. Chem. Soc. 133 2011 17283
94. L. Ackermann, and P. Novak Org. Lett. 11 2009 4966
95. L. Ackermann, P. Novák, R. Vicente, and N. Hofmann Angew. Chem., Int. Ed. 48 2009 6045
96. L. Ackermann, N. Hofmann, and R. Vicente Org. Lett. 13 2011 1875
97. F. Kakiuchi, M. Yamauchi, N. Chatani, and S. Murai Chem. Lett. 1996 111
98. F. Kakiuchi, T. Sato, T. Tsujimoto, M. Yamauchi, N. Chatani, and S. Murai Chem. Lett. 1998 1053
99. R. Martinez, R. Chevalier, S. Darses, and J.P. Genet Angew. Chem., Int. Ed. 45 2006 8232
100. 3 catalyst, the monoarylation of aldimines and ketimines was achieved at 120 °C for 20 h and diarylation of an aldimine.
101. 3 catalyst the diarylation of phenyloxazoline with phenylbromide in NMP required 20 h at 120 °C
102. 2P(O)H as the catalyst with arylchlorides at 120 °C (16-24 h) the monoarylated ketimines were isolated as the ketones after acidic hydrolysis
103. 2O) but with arylbromides at 120 °C (22 h) led to monoarylated ketimines isolated as the ketones
104. P.B. Arockiam, C. Fischmeister, C. Bruneau, and P.H. Dixneuf Angew. Chem., Int. Ed. 49 2010 6629
105. R.N. Butler, and A.G. Coyne Chem. Rev. 110 2010 6302
106. B.H. Lipshutz, A.R. Abela, Z.V. Boškovic, T. Nishikata, C. Duplais, and A. Krasovshiy Top Catal. 53 2010 985
107. C. Fischmeister, and H. Doucet Green. Chem. 13 2011 741
108. E. Ferrer Flegeau, C. Bruneau, P.H. Dixneuf, and A. Jutand J. Am. Chem. Soc. 133 2011 10161
109. F. Pozgan, and P.H. Dixneuf Adv. Synth. Catal. 351 2009 1737
110. P. Arockiam, V. Poirier, C. Fischmeister, C. Bruneau, and P.H. Dixneuf Green. Chem. 11 2009 1871
111. B. Lastra-Barreira, J. Francos, P. Crochet, and V. Cadierno Green. Chem. 13 2011 307
112. B. Lastra-Barreira, and P. Crochet Green. Chem. 12 2010 1311
113. V. Cadierno, J. Francos, and J. Gimeno Green. Chem. 12 2010 135
114. T. Brendgen, T. Fahlbusch, M. Frank, D.T. Schuhle, M. Seßler, and J. Schatza Adv. Synth. Catal. 351 2009 303
115. J. Canivet, and G. Süss-Fink Green. Chem. 9 2007 391
116. V. Cadierno, S.E. García-Garrido, J. Gimeno, A. Varela-Álvarez, and J.A. Sordo J. Am. Chem. Soc. 128 2006 1360
117. M. Saoud, A. Romerosa, and M. Peruzzini Organometallics 19 2000 4005
118. D.J. Darensbourg, F. Joo, M. Kannisto, A. Katho, and J.H. Reibenspies Organometallics 11 1992 1990
119. S. Narayan, J. Muldoon, M.G. Finn, V.V. Fokin, H.C. Kolb, and K.B. Sharpless Angew. Chem., Int. Ed. 44 2005 3275
120. V.V. Fokin, and A. Chanda Chem. Rev. 109 2009 725