Palladium-catalyzed/norbornene-mediated C-H activation/ N-tosylhydrazone insertion reaction: A route to highly functionalized vinylarenes

Chemistry - A European Journal

Volumn 20, Issue 22, 2014, Pages 6745-6751

  Zhou, Ping Xin ^a   Zheng, Lan ^a   Ma, Jun Wei ^a   Ye, Yu Ying ^a   Liu, Xue Yuan ^a   Xu, Peng Fei ^a   Liang, Yong Min ^a,b  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

C C coupling; C H activation; diazo compounds; palladium; synthetic methods

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; PALLADIUM;

C-C COUPLING; C-H ACTIVATION; DIAZO COMPOUNDS; INSERTION REACTIONS; MIGRATORY INSERTION; PALLADIUM-CATALYZED; STRAIGHT-FORWARD METHOD; SYNTHETIC METHODS;

CHEMICAL ACTIVATION;

EID: 84901324955     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201402097     Document Type: Article

References (99)

1. A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300
2. Angew. Chem. Int. Ed. 2000, 39, 3168
3. D. J. Ramõn, M. Yus, Angew. Chem. 2005, 117, 1628
4. Angew. Chem. Int. Ed. 2005, 44, 1602
5. Multicomponent reactions, (Eds.:, J. Zhu, H. Bienaymé,), Wiley-VCH, Weinheim, 2005
6. D. Tejedor, F. García-Tellado, Chem. Soc. Rev. 2007, 36, 484
7. J. D. Sunderhaus, S. F. Martin, Chem. Eur. J. 2009, 15, 1300
8. B. B. Touré, D. G. Hall, Chem. Rev. 2009, 109, 4439
9. B. Ganem, Acc. Chem. Res. 2009, 42, 463
10. J. Yu, F. Shi, L.-Z. Gong, Acc. Chem. Res. 2011, 44, 1156
11. C. de Graaff, E. Ruijter, R. V. A. Orru, Chem. Soc. Rev. 2012, 41, 3969.
12. Handbook of Organopalladium Chemistry for Organic Synthesis (Eds.:, E.-I. Negishi, A. de Meijere,), Wiley, Hoboken, 2002
13. J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 2004
14. Palladium in Organic Synthesis (Ed.:, J. Tsuji,), Springer, Berlin, 2005.
15. M. Catellani, Synlett 2003, 298
16. M. Catellani, Top. Organomet. Chem. 2005, 14, 21
17. M. Lautens, D. Alberico, C. Bressy, Y.-Q. Fang, B. Mariampillai, T. Wilhelm, Pure Appl. Chem. 2006, 78, 351
18. M. Catellani, E. Motti, N. Della Ca', Acc. Chem. Res. 2008, 41, 1512
19. P. Sehnal, R. J. K. Taylor, l. J. S. Fairlamb, Chem. Rev. 2010, 110, 824
20. A. Martins, B. Mariampillai, M. Lautens, Top. Curr. Chem. 2010, 292, 1
21. G. P. Chiusoli, M. Catellani, M. Costa, E. Motti, N. Della Ca', G. Maestri, Coord. Chem. Rev. 2010, 254, 456.
22. C.-S. Li, C.-H. Cheng, F.-L. Liao, S.-L. Wang, J. Chem. Soc. Chem. Commun. 1991, 710
23. M. Catellani, G. P. Chiusoli, J. Organomet. Chem. 1992, 425, 151
24. C.-S. Li, D.-C. Jou, C.-H. Cheng, Organometallics 1993, 12, 3945
25. C.-H. Liu, C.-S. Li, C.-H. Cheng, Organometallics 1994, 13, 18
26. M. Catellani, C. Mealli, E. Motti, P. Paoli, E. Perez-Carreño, P. S. Pregosin, J. Am. Chem. Soc. 2002, 124, 4336
27. D. J. Cárdenas, B. Martín-Matute, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 5033
28. C. Amatore, M. Catellani, S. Deledda, A. Jutand, E. Motti, Organometallics 2008, 27, 4549
29. D. I. Chai, P. Thansandote, M. Lautens, Chem. Eur. J. 2011, 17, 8175
30. G. Maestri, E. Motti, N. Della Ca', M. Malacria, E. Derat, M. Catellani, J. Am. Chem. Soc. 2011, 133, 8574.
31. M. Catellani, M. C. Fagnola, Angew. Chem. 1994, 106, 2559
32. Angew. Chem. Int. Ed. Engl. 1994, 33, 2421
33. M. Catellani, F. Frignani, A. Rangoni, Angew. Chem. 1997, 109, 142
34. Angew. Chem. Int. Ed. Engl. 1997, 36, 119
35. M. Catellani, E. Motti, S. Baratta, Org. Lett. 2001, 3, 3611
36. M. Lautens, J.-F. Paquin, S. Piguel, M. Dahlmann, J. Org. Chem. 2001, 66, 8127
37. M. Lautens, J.-F. Paquin, S. Piguel, J. Org. Chem. 2002, 67, 3972
38. S. Pache, M. Lautens, Org. Lett. 2003, 5, 4827
39. F. Faccini, E. Motti, M. Catellani, J. Am. Chem. Soc. 2004, 126, 78
40. A. Martins, U. Marquardt, N. Kasravi, D. Alberico, M. Lautens, J. Org. Chem. 2006, 71, 4937
41. F. Jafarpour, M. Lautens, Org. Lett. 2006, 8, 3601
42. E. Motti, F. Faccini, I. Ferrari, M. Catellani, R. Ferraccioli, Org. Lett. 2006, 8, 3967
43. D. Alberico, A. Rudolph, M. Lautens, J. Org. Chem. 2007, 72, 775
44. N. Della Ca', E. Motti, M. Catellani, Adv. Synth. Catal. 2008, 350, 2513
45. K. M. Gericke, D. I. Chai, M. Lautens, Tetrahedron 2008, 64, 6002
46. K. M. Gericke, D. I. Chai, N. Bieler, M. Lautens, Angew. Chem. 2009, 121, 1475
47. Angew. Chem. Int. Ed. 2009, 48, 1447
48. P. Thansandote, C. Gouliaras, M.-O. Turcotte-Savard, M. Lautens, J. Org. Chem. 2009, 74, 1791
49. N. Della Ca', E. Motti, A. Mega, M. Catellani, Adv. Synth. Catal. 2010, 352, 1451
50. H. Liu, M. El-Salfiti, D. I. Chai, J. Auffret, M. Lautens, Org. Lett. 2012, 14, 3648
51. F. Jafarpour, N. Jalalimanesh, Tetrahedron 2012, 68, 10286
52. H. Liu, M. El-Salfiti, M. Lautens, Angew. Chem. 2012, 124, 9984
53. Angew. Chem. Int. Ed. 2012, 51, 9846
54. X. Sui, R. Zhu, G. Li, X. Ma, Z. Gu, J. Am. Chem. Soc. 2013, 135, 9318.
55. M. Catellani, E. Motti, M. Minari, Chem. Commun. 2000, 157
56. E. Motti, A. Mignozzi, M. Catellani, J. Mol. Catal. A: Chem. 2003, 204-205, 115
57. B. Mariampillai, D. Alberico, V. Bidau, M. Lautens, J. Am. Chem. Soc. 2006, 128, 14436
58. B. Mariampillai, J. Alliot, M. Li, M. Lautens, J. Am. Chem. Soc. 2007, 129, 15372
59. E. Motti, N. Della Ca', S. Deledda, E. Fava, F. Panciroli, M. Catellani, Chem. Commun. 2010, 46, 4291.
60. R. Ferraccioli, D. Carenzi, O. Rombolà, M. Catellani, Org. Lett. 2004, 6, 4759
61. P. Thansandote, M. Raemy, A. Rudolph, M. Lautens, Org. Lett. 2007, 9, 5255
62. D. A. Candito, M. Lautens, Angew. Chem. 2009, 121, 6841
63. Angew. Chem. Int. Ed. 2009, 48, 6713
64. G. Maestri, N. Della Ca', M. Catellani, Chem. Commun. 2009, 4892
65. P. Thansandote, E. Chong, K.-O. Feldmann, M. Lautens, J. Org. Chem. 2010, 75, 3495
66. G. Maestri, M.-H. Larraufie, E. Derat, C. Ollivier, L. Fensterbank, E. Lacôte, M. Malacria, Org. Lett. 2010, 12, 5692
67. M. Blanchot, D. A. Candito, F. Larnaud, M. Lautens, Org. Lett. 2011, 13, 1486.
68. S. Deledda, E. Motti, M. Catellani, Can. J. Chem. 2005, 83, 741
69. T. Wilhelm, M. Lautens, Org. Lett. 2005, 7, 4053
70. K. Mitsudo, P. Thansandote, T. Wilhelm, B. Mariampillai, M. Lautens, Org. Lett. 2006, 8, 3939
71. A. Martins, M. Lautens, Org. Lett. 2008, 10, 5095
72. Z. Dong, G. Dong, J. Am. Chem. Soc. 2013, 135, 18350.
73. C. Bressy, D. Alberico, M. Lautens, J. Am. Chem. Soc. 2005, 127, 13148
74. C. Blaszykowski, E. Aktoudianakis, C. Bressy, D. Alberico, M. Lautens, Org. Lett. 2006, 8, 2043
75. A. Martins, D. Alberico, M. Lautens, Org. Lett. 2006, 8, 4827
76. C. Blaszykowski, E. Aktoudianakis, D. Alberico, C. Bressy, D. G. Hulcoop, F. Jafarpour, A. Joushaghani, B. Laleu, M. Lautens, J. Org. Chem. 2008, 73, 1888
77. B. Laleu, M. Lautens, J. Org. Chem. 2008, 73, 9164
78. A. Martins, M. Lautens, J. Org. Chem. 2008, 73, 8705
79. F. Jafarpour, H. Hazrati, Adv. Synth. Catal. 2010, 352, 363.
80. J. Barluenga, C. Valdés, Angew. Chem. 2011, 123, 7626
81. Angew. Chem. Int. Ed. 2011, 50, 7486
82. N. M. G. Franssen, A. J. C. Walters, J. N. H. Reek, B. de Bruin, Catal. Sci. Technol. 2011, 1, 153
83. Y. Zhang, J. Wang, Eur. J. Org. Chem. 2011, 1015
84. Z. Shao, H. Zhang, Chem. Soc. Rev. 2012, 41, 560
85. Y. Zhang, J. Wang, Top. Curr. Chem. 2012, 327, 239
86. Q. Xiao, Y. Zhang, J. Wang, Acc. Chem. Res. 2013, 46, 236.
87. K. L. Greenman, D. S. Carter, D. L. Van Vranken, Tetrahedron 2001, 57, 5219.
88. J. Barluenga, P. Moriel, C. Valdés, F. Aznar, Angew. Chem. 2007, 119, 5683
89. Angew. Chem. Int. Ed. 2007, 46, 5587.
90. C. Peng, Y. Wang, J. Wang, J. Am. Chem. Soc. 2008, 130, 1566.
91. L. Zhou, F. Ye, Y. Zhang, J. Wang, J. Am. Chem. Soc. 2010, 132, 13590.
92. R. Kudirka, S. K. J. Devine, C. S. Adams, D. L. Van Vranken, Angew. Chem. 2009, 121, 3731
93. Angew. Chem. Int. Ed. 2009, 48, 3677.
94. Z.-S. Chen, X.-H. Duan, P.-X. Zhou, S. Ali, J.-Y. Luo, Y.-M. Liang, Angew. Chem. 2012, 124, 1399
95. Angew. Chem. Int. Ed. 2012, 51, 1370.
96. J. Barluenga, L. Florentino, F. Aznar, C. Valdés, Org. Lett. 2011, 13, 510
97. J. Barluenga, M. Escribano, F. Aznar, C. Valdés, Angew. Chem. 2010, 122, 7008
98. Angew. Chem. Int. Ed. 2010, 49, 6856.
99. The molecular structure of 4-38 was determined on the basis of X-ray crystallographic studies. CCDC-981521 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.