A palladium-catalyzed oxidative cycloaromatization of biaryls with alkynes using molecular oxygen as the oxidant

Angewandte Chemie - International Edition

Volumn 48, Issue 42, 2009, Pages 7895-7898

  Shi, Zhuangzhi ^a   Ding, Shengtao ^a   Cui, Yuxin ^a   Jiao, Ning ^b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

Alkynes; Biaryls; C H activation; Oxidation; Palladium

Indexed keywords

ALKYNES; BIARYLS; C-H ACTIVATION; C-H BOND; CYCLOAROMATIZATION; DUAL ACTIVATION; HETEROAROMATICS; POLYCYCLIC AROMATICS;

ACETYLENE; ACTIVATION ANALYSIS; OXIDANTS; OXIDATION; PALLADIUM;

MOLECULAR OXYGEN;

ALKYNE; OXIDIZING AGENT; OXYGEN; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKYNES; CATALYSIS; CYCLIZATION; OXIDANTS; OXIDATION-REDUCTION; OXYGEN; PALLADIUM; POLYCYCLIC HYDROCARBONS, AROMATIC;

EID: 70349653362     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200903975     Document Type: Article

References (78)

1. a) R. G. Taylor, Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity, Cambridge University Press, Cambridge, UK, 1991;
2. b) H. Knölker, K. R. Reddy, Chem. Rev. 2002, 102, 4303;
3. c) J. Jacob, Polycyclic Aromát. Compd. 2008, 28, 242.
4. a) J. R. Lakowicz, Principles of Fluorescence Spectroscopy, Plenum, New York, 1999;
5. b) U. Mitschke, P. J. Bäuerle, Mater. Chem. 2000, 10, 1471;
6. c) M. D. Watson, A. Fechtenktter, K. Mllen, Chem. Rev. 2001, 101, 1267;
7. d) J. E. Anthony, Angew. Chem. 2008, 120, 460;
8. Angew. Chem. Int Ed. 2008, 47, 452;
9. e) M. Mazur, P. Krysinski, G. J. Blanchard, Langmuir 2005, 21, 8802;
10. f) W. Pisula, Z. Tomovic, M. Stepputat, U Kolb, T. Pakula, K. Muellen, Chem. Mater. 2005, 17, 2641;
11. g) S. Debnath, Q. Cheng, T. G. Hedderman, H. J. Byrne, J. Phys. Chem. C 2008, 112, 10418;
12. h) T. Okazaki, K. K. Laali, Adv. Org. Synth. 2006, 2, 353.
13. For reviews, see: a) R. G. Harvey. Polycyclic Aromatic Hydrocarbons, Wiley-VCH, New York, NY, 1997;
14. b) R. G. Harvey, Curr. Org. Chem. 2004, 8, 303;
15. c) H.-J. Knölker, K. R. Reddy, Chem. Rev. 2002,102, 4303;
16. d) H.-J. Knölker, Top. Curr. Chem. 2005, 244, 115;
17. e) H.-J. Knölker, Curr. Org. Synth. 2004, 1, 309;
18. f) A. X Floyd, S. F. Dyke, S. E. Ward, Chem. Rev. 1976, 76, 509.
19. For reviews on palladium-catalyzed annulation of alkynes, see: a) R. C Larock in Acetylene Chemistry: Chemistry, Biology, and Material Science (Eds.: F. Diederich, P. J. Stang, R. R. Tykwinski), Wiley-VCH, New York, 2005, Chapter 2, pp. 5.1-99;
20. b) R. C. Larock, Top. Organomet. Chem. 2005, 14, 147;
21. c) G. Zeni, R. C. Larock, Chem. Rev. 2006, 106, 4644;
22. d) E. Guitián, D. Pérez, D. Peña, Top. Organomet. Chem. 2005, 14, 109;.
23. For recent examples, see : a) S. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318;
24. b) M. Lautens, P. Thansandote, Chem. Eur. J. 2009, 15, 5874;
25. c) T. Gerfaud, L. Neuville, J. Zhu, Angew. Chem. 2009, 121, 580;
26. Angew. Chem. Int. Ed. 2009, 48, 572;
27. d) D. R. Stuart, M. Bertrand-Laperle, K. M. N. Burgess, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 16474;
28. e) K. Inamoto, C Hasegawa, K. Hiroya, T. Doi, Org. Lett. 2008, 10, 5147;
29. f) S. Würtz, S. Raksh.it, J. J. Neumann, T. Droge, F. Glorius, Angew. Chem. 2008, 120, 7340;
30. Angew. Chem. Int. Ed. 2008, 47, 7230;
31. g) N. Chernyak, V., Gevoorgyan, J. Am. Chem. Soc. 2008, 130, 5636;
32. h) V. S. Thirunavukkarasu, K. Parthasarathy, C.-H. Cheng, Angew. Chem. 2008, 120, 9604;
33. Angew. Chem. Int Ed. 2008, 47, 9462;
34. i) X. Wan, D. Xing, Z. Fang, B. Li, F. Zhao, K. Zhang, L. Yang, Z. Shi, J. Am. Chem. Soc. 2006, 128, 12046;
35. j) K. K. Grüner, H.-J. Knölker, Org. Biomol. Chem. 2008, 6, 3902.
36. a) U. Umeda, H. Tsurugi, T. Satoh, M. Miura. Angew. Chem. 2008,120, 4083;
37. Angew. Chem. Int Ed. 2008, 47, 4019;
38. Angew. Chem. Int. Ed. 2008, 47, 4019;
39. b) Y.-T. Wu, K.-H. Huang, C.-C. Shin, T.-C. Wu, Chem. Eur. J. 2008, 14, 6697.
40. D. R. Stuart, K. Fagnou, Science 2007, 316, 1172.
41. Z. Shi, C. Zhang, S. Li, D. Pan, S. Ding, Y Cui, N. Jiao, Angew. Chem. 2009, 121, 4642;
42. Angew. Chem. Int Ed. 2009, 48, 4572.
43. Dioxygen is an ideal oxidant and offers attractive industrial prospects in terms of green and sustainable chemistry, for reviews see: a) M. Costas, M. P. Mehn, M. P. Jensen, L. Que, Jr., Chem. Rev. 2004, 104, 939;
44. b) S. S. Stahl, Angew. Chem. 2004, 116, 3480;
45. Angew. Chem. Int. Ed. 2004, 43, 3400;
46. c) T. Punniyamurthy, S. Velusamy, X Iqbal, Chem. Rev. 2005, 105, 2329;
47. d) B. V. Popp, S. S. Stahl, Top. Organomet. Chem. 2007, 22, 149;
48. for palladium-catalyzed examples, see: e) S. S. Stahl, J. L. Thorman, R. Nelson, M. A. Kozee, J. Am. Chem. Soc. 2001, 123, 7188;
49. f) S. S. Stahl, Science 2005, 309, 1824-1826;
50. g) R. J. Nielsen, W. A. Goddard III, J. Am Chem. Soc. 2006, 128, 9651;
51. h) B. A. Steinhoff, S. S. Stahl, J. Am Chem. Soc. 2006, 128, 4348;
52. i) B. Li, S. Tian, Z. Fang, Z. Shi, Angew. Chem. 2008, 120, 1131;
53. Angew. Chem. Int. Ed. 2008, 47,1115;
54. j) G. Liu, G. Yin, L. Wu, Angew. Chem. 2008, 120, 4811;
55. Angew. Chem. Int. Ed. 2008, 47, 4733;
56. k) D.-H. Wang, M. Wasa, R. Giri, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 7190;
57. l) M. M. Konnick, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 5753.
58. .1.0] a) R. X Phipps, N. P. Grimster, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 8172;
59. b) E. M. Beck, R. Hatley, M. J. Gaunt, J. Am. Chem. Soc. 2006, 128, 2528;
60. c) N. P. Grimster, C Gauntlett, C. M. R. Godfrey, M. X Gaunt, Angew. Chem. 2005, 117, 3185;
61. Angew. Chem. Int. Ed. 2005, 44, 3125;
62. d) E. M. Ferreira, B. M. Stoltz, J. Am. Chem. Soc. 2003, 125, 9578;
63. e) T. A. Dwight, N. R. Rue, D. Charyk, R. Josselyn, B. Deboef, Org. Lett. 2007, 9, 3137;
64. f) A. Kong, X. Han, X. Lu, Org. Lett. 2006, 8, 1339;
65. g) Y. Fujiwara, I. Moritani, S. Danno, R. Asano, S. Teranishi, J. Am. Chem. Soc. 1969, 91, 7166;
66. h) I. Moritani, Y. Fujiwara, Tetrahedron Lett. 1967, 1119.
67. a) C. Jia, T. Kitamura, Y. Fujiwara, Ace Chem. Res 2001, 34, 633;
68. b) A. M. Echavarren, B. Gómez-Lor, J. J. González, Ó. de Frutos, Synlett 2003, 585.
69. a) R. C. Larock, M. J. Doty, Q. Tian, J.. Zenner, J. Org. Chem. 1997, 62, 7536;
70. b) H. Zhang, R. C. Larock, J. org. Chem. 2002, 67, 9318;
71. c) H. Zhang, R. C. Larock, J. Org. Chem. 2003, 68, 5132;
72. d) S. Kawasaki, T. Satoh, M. Miura, M. Nomura, J. Org. Chem. 2003, 68, 6836.
73. .1.3] Selected recent examples of transition-metal-catalyzed synthesis of fluorescent compounds: a) T. Tsuchimoto, H. Matsubayashi, M. Kaneko, Y Nagase, T. Miyamura, E. Shirakawa, J. Am. Chem. Soc. 2008, 130, 15823;
74. b) M. Miyasaka, A. Fukushima, T. Satoh, K. Hirano, M. Miura, Chem. Eur. J. 2009, 15, 3674.
75. c) Y.-T. Wu, M.-Y. Kuo, Y.-T. Chang, C.-C. Shin, T.- C. Wu, C.-C. Tai, T.-H. Cheng, W.-S. Liu. Angew. Chem. 2008, 120, 10039;
76. Angew. Chem. Int. Ed. 2008, 47, 9891;
77. Angew. Chem. Int. Ed. 2008, 47, 9891;
78. d) M. Yamashita, K, Hirano, T. Satoh, M. Miura, Org. Lett. 2009, 11, 2337.