Palladium-catalyzed construction of heteroatom-containing π-conjugated systems by intramolecular oxidative C-H/C-H coupling reaction

Chemistry - A European Journal

Volumn 21, Issue 23, 2015, Pages 8365-8368

  Saito, Kenta ^a   Chikkade, Prasanna Kumara ^a   Kanai, Motomu ^a,b   Kuninobu, Yoichiro ^a,b  

^a UNIVERSITY OF TOKYO   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

C H activation; C H C H coupling; heteroatom; palladium; pi conjugated system

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; CHEMICAL REACTIONS; MOLECULES; PALLADIUM;

C-H ACTIVATION; CONJUGATED MOLECULES; COUPLING REACTION; CROSS COUPLING REACTIONS; CYCLOAROMATIZATION; HETEROATOMS; PALLADIUM-CATALYZED; PI-CONJUGATED SYSTEM;

SYNTHESIS (CHEMICAL);

EID: 84930221644     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201501116     Document Type: Article

References (71)

1. U. Scherf, J. Mater. Chem. 1999, 9, 1853
2. A. Fukazawa, S. Yamaguchi, Chem. Asian J. 2009, 4, 1386
3. K. Takimiya, S. Shinamura, I. Osaka, E. Miyazaki, Adv. Mater. 2011, 23, 4347
4. J.-S. Wu, S.-W. Cheng, Y.-J. Cheng, C.-S. Hsu, Chem. Soc. Rev. 2015, 44, 1113.
5. J. Dubac, A. Laporterie, G. Manuel, Chem. Rev. 1990, 90, 215
6. R. F. Chen, Q. L. Fan, C. Zheng, W. Huang, Org. Lett. 2006, 8, 203.
7. S. Yamaguchi, C. Xu, K. Tamao, J. Am. Chem. Soc. 2003, 125, 13662.
8. For a recent review, see:, J. Wencel-Delord, F. Glorius, Nat. Chem. 2013, 5, 369.
9. M. Shimizu, K. Mochida, T. Hiyama, Angew. Chem. Int. Ed. 2008, 47, 9760
10. Angew. Chem. 2008, 120, 9906
11. K. Mochida, M. Shimizu, T. Hiyama, J. Am. Chem. Soc. 2009, 131, 8350
12. R. Shintani, H. Otomo, K. Oka, T. Hayashi, J. Am. Chem. Soc. 2012, 134, 7305.
13. T. Ureshino, T. Yoshida, Y. Kuninobu, K. Takai, J. Am. Chem. Soc. 2010, 132, 14324
14. Y. Kuninobu, T. Yoshida, K. Takai, J. Org. Chem. 2011, 76, 7370
15. Y. Kuninobu, K. Origuchi, K. Takai, Heterocycles 2012, 85, 3029
16. Y. Kuninobu, K. Yamauchi, N. Tamura, T. Seiki, K. Takai, Angew. Chem. Int. Ed. 2013, 52, 1520
17. Angew. Chem. 2013, 125, 1560.
18. Q. Xiao, X. Meng, M. Kanai, Y. Kuninobu, Angew. Chem. Int. Ed. 2014, 53, 3168
19. Angew. Chem. 2014, 126, 3232.
20. W. Han, A. R. Ofial, Synlett 2011, 1951 (catalytic reactions)
21. K. Hirano, M. Miura, Chem. Commun. 2012, 48, 10704 (stoichiometric reactions).
22. S.-L. You, J.-B. Xia, Top. Curr. Chem. 2009, 292, 165
23. C. S. Yeung, V. M. Dong, Chem. Rev. 2011, 111, 1215.
24. K. Masui, H. Ikegami, A. Mori, J. Am. Chem. Soc. 2004, 126, 5074.
25. Y. Li, J. Jin, W.-X. Qian, W.-L. Bao, Org. Biomol. Chem. 2010, 8, 326
26. P. Xi, F. Yang, S. Qin, D. Zhao, J. Lan, G. Gao, C. Hu, J. You, J. Am. Chem. Soc. 2010, 132, 1822
27. W. Han, P. Mayer, A. R. Ofial, Angew. Chem. Int. Ed. 2011, 50, 2178
28. Angew. Chem. 2011, 123, 2226
29. H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2011, 133, 13577
30. N. Kuhl, M. N. Hopkinson, F. Glorius, Angew. Chem. Int. Ed. 2012, 51, 8230
31. Angew. Chem. 2012, 124, 8354.
32. Y. Izawa, S. S. Stahl, Adv. Synth. Catal. 2010, 352, 3223.
33. D. R. Stuart, K. Fagnou, Science 2007, 316, 1172
34. D. R. Stuart, E. Villemure, K. Fagnou, J. Am. Chem. Soc. 2007, 129, 12072
35. T. A. Dwight, N. R. Rue, D. Charyk, R. Josselyn, B. DeBoef, Org. Lett. 2007, 9, 3137
36. S. Potavathri, A. S. Dumas, T. A. Dwight, G. R. Naumiec, J. M. Hammann, B. DeBoef, Tetrahedron Lett. 2008, 49, 4050
37. C. C. Malakar, D. Schmidt, J. Conrad, U. Beifuss, Org. Lett. 2011, 13, 1378. See also, Ref. [11d].
38. H. Li, J. Liu, C.-L. Sun, B.-J. Li, Z.-J. Shi, Org. Lett. 2011, 13, 276.
39. M. Kitahara, N. Umeda, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2011, 133, 2160
40. M. Nishino, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2012, 51, 6993
41. Angew. Chem. 2012, 124, 7099
42. M. Nishino, K. Hirano, T. Satoh, M. Miura, Angew. Chem. Int. Ed. 2013, 52, 4457
43. Angew. Chem. 2013, 125, 4553.
44. K. L. Hull, M. S. Sanford, J. Am. Chem. Soc. 2007, 129, 11904
45. J. Wencel-Delord, C. Nimphius, H. Wang, F. Glorius, Angew. Chem. Int. Ed. 2012, 51, 13001
46. Angew. Chem. 2012, 124, 13175
47. J. Dong, Z. Long, F. Song, N. Wu, Q. Guo, J. Lan, J. You, Angew. Chem. Int. Ed. 2013, 52, 580
48. Angew. Chem. 2013, 125, 608
49. X. Qin, H. Liu, D. Qin, Q. Wu, J. You, D. Zhao, Q. Guo, X. Huang, J. Lan, Chem. Sci. 2013, 4, 1964
50. B. Liu, Y. Huang, J. Lan, F. Song, J. You, Chem. Sci. 2013, 4, 2163.
51. B. Akermark, L. Eberson, E. Jonsson, E. Petterson, J. Org. Chem. 1975, 40, 1365
52. T. Watanabe, S. Ueda, S. Inuki, S. Oishi, N. Fujii, H. Ohno, Chem. Commun. 2007, 4516
53. B. Liégault, D. Lee, M. P. Huestis, D. R. Stuart, K. Fagnou, J. Org. Chem. 2008, 73, 5022
54. T. Watanabe, S. Oishi, N. Fujii, H. Ohno, J. Org. Chem. 2009, 74, 4720
55. H. J. Knölker, Chem. Lett. 2009, 38, 8.
56. A. Shiotani, H. Itatani, Angew. Chem. Int. Ed. Engl. 1974, 13, 471
57. Angew. Chem. 1974, 86, 478.
58. N. Ishida, Y. Nakanishi, T. Morita, M. Murakami, Chem. Lett. 2011, 40, 1047.
59. K. Morimoto, M. Itoh, K. Hirano, T. Satoh, Y. Shibata, K. Tanaka, M. Miura, Angew. Chem. Int. Ed. 2012, 51, 5359
60. Angew. Chem. 2012, 124, 5455.
61. H. Li, R.-Y. Zhu, W.-J. Shi, K.-H. He, Z.-J. Shi, Org. Lett. 2012, 14, 4850
62. P. Gandeepan, C.-H. Hung, C.-H. Cheng, Chem. Commun. 2012, 48, 9379.
63. L. Ackermann, R. Jeyachandran, H. K. Potukuchi, P. Novák, L. Buttner, Org. Lett. 2010, 12, 2056
64. D. G. Pintori, M. F. Greaney, J. Am. Chem. Soc. 2011, 133, 1209
65. M. Sun, H. Wu, J. Zhen, W. Bao, Adv. Synth. Catal. 2012, 354, 835
66. G. Meng, H.-Y. Niu, G.-R. Qu, J. D. Fossey, J.-P. Li, H.-M. Guo, Chem. Commun. 2012, 48, 9601
67. V. P. Reddy, T. Iwasaki, N. Kambe, Org. Biomol. Chem. 2013, 11, 2249. See also, ref. [13c].
68. S. K. Guchhait, M. Kashyap, S. Kandekar, Tetrahedron Lett. 2012, 53, 3919.
69. Y. Ma, J. You, F. Song, Chem. Eur. J. 2013, 19, 1189
70. P. Oechsle, J. Paradies, Org. Lett. 2014, 16, 4086.
71. A. J. Bard, R. Parsons, J. Jordan, Standard Potentials in Aqueous Solution, CRC Press, Florida, 1985.