Multiple C-H activations to construct biologically active molecules in a process completely free of organohalogen and organometallic components

Angewandte Chemie - International Edition

Volumn 47, Issue 6, 2008, Pages 1115-1118

  Li, Bi Jie ^c   Tian, Shi Liang ^c   Fang, Zhao ^c   Shi, Zhang Jie ^a,b  

^a PEKING UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c PEKING UNIVERSITY   (China)

Author keywords

C C coupling; C H activation; Dehydrogenation; Homogeneous catalysis; Palladium

Indexed keywords

BIOACTIVITY; DEHYDROGENATION; HYDROGEN BONDS; MOLECULES; PALLADIUM COMPOUNDS;

BIARYLS; HOMOGENEOUS CATALYSIS; ORGANOMETALLIC COMPONENTS;

ORGANOMETALLICS;

CARBON; CROSS LINKING REAGENT; HYDROGEN; METAL; ORGANIC COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; HALOGENATION;

CARBON; CATALYSIS; CROSS-LINKING REAGENTS; HALOGENATION; HYDROGEN; METALS; MOLECULAR STRUCTURE; ORGANIC CHEMICALS;

EID: 38849126856     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704092     Document Type: Article

References (64)

1. a) S. Murai, Activation of Unreactive Bonds and Organic Synthesis, Springer, Berlin, 1999, pp. 48-78;
2. b) A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879;
3. c) F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077;
4. d) G. Dyker, Angew. Chem. 1999, 111, 1808;
5. Angew. Chem. Int. Ed. 1999, 38, 1698;
6. e) S. S. Stahl, J. A. Labinger, J. E. Bercaw, Angew. Chem. 1998, 110, 2298;
7. Angew. Chem. Int. Ed. 1998, 37, 2180;
8. f) A. R. Dick, M. S. Sanford, Tetrahedron 2006, 62, 2439;
9. g) B. A. Arndtsen, R. G. Bergman, T. A. Mobley, T. H. Peterson, Acc. Chem. Res. 1995, 28, 154;
10. h) J. A. Labinger, J. E. Bercaw, Nature 2002, 417, 507;
11. i) Y. Guari, S. Sabo-Etienne, B. Chaudret, Eur. J. Inorg. Chem. 1999, 1047.
12. a) V. Ritleng, C. Sirlin, M. Pfeffer, Chem. Rev. 2002, 102, 1731;
13. b) J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527;
14. c) S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, Nature 1993, 366, 529;
15. d) S. Oi, Y. Ogino, S. Fukita, Y. Inoue, Org. Lett. 2002, 4, 1783;
16. e) K. L. Tan, R. G. Bergman, J. A. Ellman, J. Am. Chem. Soc. 2002, 124, 13964;
17. f) C.-H. Jun, J.-B. Hong, Y.-H. Kim, K.-Y. Chung, Angew. Chem. 2000, 112, 3582;
18. Angew. Chem. Int. Ed. 2000, 39, 3440;
19. g) J.-Y. Cho, M. K. Tse, D. Holmes, R. E. Maleczka, M. R. Smith III, Science 2002, 295, 305;
20. h) H. Y. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995;
21. i) C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992.
22. a) M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586;
23. b) V. G. Zaitsev, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 4156;
24. c) M. T. Reetz, K. Sommer, Eur. J. Org. Chem. 2003, 3485;
25. d) J. Zhao, M. Campo, R. C. Larock, Angew. Chem. 2005, 117, 1907;
26. Angew. Chem. Int. Ed. 2005, 44, 1873;
27. e) X. Chen, J.-J. Li, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 78;
28. f) D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330;
29. g) B. S. Lane, M. A. Brown, D. Sames, J. Am. Chem. Soc. 2005, 127, 8050;
30. h) R. K. Thalji, J. A. Ellman, R. G. Bergman, J. Am. Chem. Soc. 2004, 126, 7192.
31. C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633.
32. K. Godula, D. Sames, Science 2006, 312, 67.
33. Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Dieterich, P. J. Stang), Wiley-VCH, New York, 1998.
34. a) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174;
35. b) T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. 1997, 109, 1820;
36. Angew. Chem. Int. Ed. Engl. 1997, 36, 1740;
37. c) L. Ackermann, A. Althammer, R. Born, Angew. Chem. 2006, 118, 2681;
38. Angew. Chem. Int. Ed. 2006, 45, 2619;
39. d) J. Zhao, D. Yue, M. A. Campo, R. C. Larock, J. Am. Chem. Soc. 2007, 129, 5288;
40. e) K.-I. Fujita, M. Nonogawa, R. Yamaguchi, Chem. Commun. 2004, 1926;
41. f) O. Daugulis, V. G. Zaitsev, D. Shabashov, Q. N. Pham, A. Lazareva, Synlett 2006, 3382;
42. g) R. Giri, N. Maugel, J.-J. Li, D.-H. Wang, S. P. Breazzano, L. B. Saunders, J.-Q. Yu, J. Am. Chem. Soc. 2007, 129, 3510;
43. h) F. Kakiuchi, S. Kan, K. Igi, N. Chatani, S. Murai, J. Am. Chem. Soc. 2003, 125, 1698;
44. i) S. Yang, B. Li, X. Wan, Z, Shi, J. Am. Chem. Soc. 2007, 129, 6066;
45. j) S. Oi, S. Fukita, Y. Inoue, Chem. Commun. 1998, 2439.
46. a) K. L. Hull, E. L. Lanni, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 14047;
47. b) K. Masui, H. Ikegami, A. Mori, J. Am. Chem. Soc. 2004, 126, 5074;
48. c) H. Iataaki, H. Yoshimoto, J. Org. Chem. 1973, 38, 76.
49. a) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 3672;
50. b) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 6968.
51. R. Li, L. Jiang, W. Lu, Organometallics 2006, 25, 5973.
52. D. R. Stuart, K. Fagnou, Science 2007, 316, 1172.
53. T. A. Dwight, N. R. Rue, D. Charyk, R. Josselyn, B. DeBoef, Org. Lett. 2007, 9, 3137.
54. a) X. Wan, Z. Ma, B. Li, K. Zhang, S. Cao, S. Zhang, Z. Shi, J. Am. Chem. Soc. 2006, 128, 7416;
55. b) Z. Shi, B. Li, X. Wan, J. Cheng, Z. Fang, B. Cao, C. Qin, Y. Wang, Angew. Chem. 2007, 119, 5650;
56. Angew. Chem. Int. Ed. 2007, 46, 5554.
57. a) T. Ishiyama, K. Sato, Y. Nishio, N. Miyaura, Angew. Chem. 2003, 115, 5504;
58. Angew. Chem. Int. Ed. 2003, 42, 5346;
59. b) N. Tsukada, T. Mitsuboshi, H. Setoguchi, Y. Inoue, J. Am. Chem. Soc. 2003, 125, 12102, and references therein.
60. a) D. García-Cuadrado, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 1066;
61. b) M. Lafrance, C. N. Rowley, T. K. Woo, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 8754.
62. H. J. Knölker, K. R. Reddy, Chem. Rev. 2002, 102, 4303.
63. W. C. P. Tsang, N. Zheng, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 14560.
64. B. K. Chowdhury, S. Jha, Synth. Commun. 2001, 31, 1559.