Investigation and comparison of the mechanistic steps in the [(Cp*MCl2)2] (Cp*=C5Me5; M=Rh, Ir)-catalyzed oxidative annulation of isoquinolones with alkynes

Chemistry - A European Journal

Volumn 19, Issue 1, 2013, Pages 358-364

  Wang, Nuancheng ^a   Li, Bin ^a   Song, Haibin ^a   Xu, Shansheng ^a   Wang, Baiquan ^a,b  

^a NANKAI UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

C H activation; iridium; oxidative annulation; reaction mechanisms; rhodium

Indexed keywords

C-H ACTIVATION; CATALYTIC CYCLES; HIGH YIELD; IR COMPLEXES; IRIDIUM COMPLEX; MECHANISTIC STUDIES; OXIDATIVE ANNULATION; OXIDATIVE COUPLINGS; REACTION MECHANISM; SINGLE CRYSTAL X-RAY DIFFRACTION ANALYSIS;

ACETYLENE; ACTIVATION ANALYSIS; CATALYSIS; IRIDIUM; IRIDIUM COMPOUNDS; RHODIUM; X RAY DIFFRACTION ANALYSIS;

RHODIUM COMPOUNDS;

EID: 84871550820     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203374     Document Type: Article

References (83)

1. K. M. Engle, T.-S. Mei, M. Wasa, J.-Q. Yu, Acc. Chem. Res. 2012, 45, 788
2. D. A. Colby, A. S. Tsai, R. G. Bergman, J. A. Ellman, Acc. Chem. Res. 2012, 45, 814
3. L. Ackermann, Chem. Rev. 2011, 111, 1315
4. J. Wencel-Delord, T. Dröge, F. Liu, F. Glorius, Chem. Soc. Rev. 2011, 40, 4740
5. A. E. Wendlandt, A. M. Suess, S. S. Stahl, Angew. Chem. 2011, 123, 11256
6. Angew. Chem. Int. Ed. 2011, 50, 11062
7. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Rev. 2011, 111, 1293
8. P. Herrmann, T. Bach, Chem. Soc. Rev. 2011, 40, 2022
9. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215
10. D. A. Colby, R. G. Bergman, J. A. Ellman, Chem. Rev. 2010, 110, 624
11. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147
12. M. C. Willis, Chem. Rev. 2010, 110, 725
13. L. Ackermann, H. K. Potukuchi, Org. Biomol. Chem. 2010, 8, 4503
14. Topics in Current Chemistry, Vol. 292, C-H Activation (Eds.:, J.-Q. Yu, Z.-J. Shi,), Springer, Berlin, 2010
15. C.-L. Sun, B.-J. Li, Z.-J. Shi, Chem. Commun. 2010, 46, 677
16. R. Jazzar, J. Hitce, A. Renaudat, J. Sofack-Kreutzer, O. Baudoin, Chem. Eur. J. 2010, 16, 2654
17. A. S. Dudnik, V. Gevorgyan, Angew. Chem. 2010, 122, 2140
18. Angew. Chem. Int. Ed. 2010, 49, 2096
19. P. Sehnal, R. J. K. Taylor, I. J. S. Fairlamb, Chem. Rev. 2010, 110, 824
20. D. Balcells, E. Clot, O. Eisenstein, Chem. Rev. 2010, 110, 749
21. R. Giri, B.-F. Shi, K. M. Engle, N. Maugel, J.-Q. Yu, Chem. Soc. Rev. 2009, 38, 3242
22. L. Ackermann, R. Vicente, A. Kapdi, Angew. Chem. 2009, 121, 9976
23. Angew. Chem. Int. Ed. 2009, 48, 9792
24. X. Chen, K. M. Engle, D.-H. Wang, J.-Q. Yu, Angew. Chem. 2009, 121, 5196
25. Angew. Chem. Int. Ed. 2009, 48, 5094
26. P. Thansandote, M. Lautens, Chem. Eur. J. 2009, 15, 5874
27. O. Daugulis, H.-Q. Do, D. Shabashov, Acc. Chem. Res. 2009, 42, 1074.
28. Heterocyclic Chemistry, 4 th ed., (Eds: J. A. Joule, K. Mills,), Blackwell, Oxford, 2000
29. The Chemistry of Heterocycles, (Eds:, T. Eicher, S. Hauptmann,) Wiley-VCH, Weinheim, 2003
30. Handbook of Heterocyclic Chemistry, 2 nd ed., (Eds: A. R. Katrizky, A. F. Pozharskii,), Pergamon, Amsterdam, 2000.
31. T. Satoh, M. Miura, Chem. Eur. J. 2010, 16, 11212
32. T. Satoh, M. Miura, Synthesis 2010, 3395
33. C. Zhu, R. Wang, J. R. Falck, Chem. Asian J. 2012, 7, 1502
34. G. Song, F. Wang, X. Li, Chem. Soc. Rev. 2012, 41, 3651.
35. N. Guimond, S. I. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2011, 133, 6449
36. M. P. Huestis, L. Chan, D. R. Stuart, K. Fagnou, Angew. Chem. 2011, 123, 1374
37. Angew. Chem. Int. Ed. 2011, 50, 1338
38. T. K. Hyster, T. Rovis, Chem. Sci. 2011, 2, 1606
39. F. W. Patureau, T. Besset, N. Kuhl, F. Glorius, J. Am. Chem. Soc. 2011, 133, 2154
40. X. Zhang, D. Chen, M. Zhao, J. Zhao, A. Jia, X. Li, Adv. Synth. Catal. 2011, 353, 719
41. K. Muralirajan, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2011, 123, 4255
42. Angew. Chem. Int. Ed. 2011, 50, 4169
43. Y.-F. Wang, K. K. Toh, J.-Y. Lee, S. Chiba, Angew. Chem. 2011, 123, 6049
44. Angew. Chem. Int. Ed. 2011, 50, 5927
45. P. C. Too, S. H. Chua, S. H. Wong, S. Chiba, J. Org. Chem. 2011, 76, 6159
46. D. R. Stuart, P. Alsabeh, M. Kuhn, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 18326
47. N. Guimond, C. Gouliaras, K. Fagnou, J. Am. Chem. Soc. 2010, 132, 6908
48. T. K. Hyster, T. Rovis, J. Am. Chem. Soc. 2010, 132, 10565
49. S. Rakshit, F. W. Patureau, F. Glorius, J. Am. Chem. Soc. 2010, 132, 9585
50. G. Song, D. Chen, C. Pan, R. H. Crabtree, X. Li, J. Org. Chem. 2010, 75, 7487
51. Y. Su, M. Zhao, K. Han, G. Song, X. Li, Org. Lett. 2010, 12, 5462
52. J. Chen, G. Song, C.-L. Pan, X. Li, Org. Lett. 2010, 12, 5426
53. P. C. Too, Y.-F. Wang, S. Chiba, Org. Lett. 2010, 12, 5688
54. K. Morimoto, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 2068
55. S. Mochida, N. Umeda, K. Hirano, T. Satoh, M. Miura, Chem. Lett. 2010, 39, 744
56. N. Guimond, K. Fagnou, J. Am. Chem. Soc. 2009, 131, 12050
57. T. Fukutani, N. Umeda, K. Hirano, T. Satoh, M. Miura, Chem. Commun. 2009, 5141
58. D. R. Stuart, M. Bertrand-Laperle, K. M. N. Burgess, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 16474
59. L. Li, W. W. Brennessel, W. D. Jones, J. Am. Chem. Soc. 2008, 130, 12414
60. N. Umeda, H. Tsurugi, T. Satoh, M. Miura, Angew. Chem. 2008, 120, 4083
61. Angew. Chem. Int. Ed. 2008, 47, 4019; less-expensive metal catalysts have recently been used for the oxidative annulation of alkynes, see
62. L. Ackermann, A. V. Lygin, N. Hofmann, Angew. Chem. 2011, 123, 6503
63. Angew. Chem. Int. Ed. 2011, 50, 6379
64. B. Li, H. Feng, S. Xu, B. Wang, Chem. Eur. J. 2011, 17, 12573
65. H. Shiota, Y. Ano, Y. Aihara, Y. Fukumoto, N. Chatani, J. Am. Chem. Soc. 2011, 133, 14952.
66. B. Li, H. Feng, N. Wang, J. Ma, H. Song, S. Xu, B. Wang, Chem. Eur. J. 2012, 18, 12873.
67. For the crystal data, see the Supporting Information, Tables S2 and S3.
68. Y. Boutadla, D. L. Davies, R. C. Jones, K. Singh, Chem. Eur. J. 2011, 17, 3438
69. Y.-F. Han, H. Li, P. Hu, G.-X. Jin, Organometallics 2011, 30, 905
70. Y. Boutadla, O. Al-Duaij, D. L. Davies, G. A. Griffith, K. Singh, Organometallics 2009, 28, 433
71. L. Li, W. W. Brennessel, W. D. Jones, Organometallics 2009, 28, 3492
72. C. Scheeren, F. Maasarani, A. Hijazi, J.-P. Djukic, M. Pfeffer, S. D. Zarić, X.-F. Le Goff, L. Ricard, Organometallics 2007, 26, 3336
73. D. L. Davies, S. M. A. Donald, O. Al-Duaij, S. A. Macgregor, M. Pölleth, J. Am. Chem. Soc. 2006, 128, 4210
74. D. L. Davies, O. Al-Duaij, J. Fawcett, M. Giardiello, S. T. Hilton, D. R. Russell, Dalton Trans. 2003, 4132
75. J. M. Kisenyi, G. J. Sunley, J. A. Cabeza, A. J. Smith, H. Adams, N. J. Salt, P. M. Maitlis, J. Chem. Soc. Dalton Trans. 1987, 2459.
76. J. M. Huggins, R. G. Bergman, J. Am. Chem. Soc. 1981, 103, 3002
77. F. Maassarani, M. Pfeffer, G. L. Borgne, Organometallics 1987, 6, 2043
78. K. R. Reddy, K. Surekha, G.-H. Lee, S.-M. Peng, S.-T. Liu, Organometallics 2001, 20, 5557.
79. A. Bisello, A. Ceccon, A. Gambaro, P. Ganis, F. Manoli, S. Santi, A. Venzo, J. Organomet. Chem. 2000, 593-594, 315.
80. E. F. Flegeau, C. Bruneau, P. H. Dixneuf, A. Jutand, J. Am. Chem. Soc. 2011, 133, 10161
81. M. Livendahl, A. M. Echavarren, Isr. J. Chem. 2010, 50, 630.
82. G. M. Sheldrick, Program for Empirical Absorption Correction of Area Detector data; University of Göttingen, Göttingen, Germany, 1996.
83. G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures from Diffraction Data; University of Göttingen, Göttingen, Germany, 1997.