Erratum: Suzuki-Miyaura coupling reaction by PdII-catalyzed aromatic C-H bond activation directed by an N-alkyl acetamino group (Angewandante Chemie - International Edition (2007) 46, (5554-5558) DOI: 10.1002/anie.200700590);Suzuki-Miyaura coupling reaction by PdII-catalyzed aromatic C-H bond activation directed by an N-alkyl acetamino group

Angewandte Chemie - International Edition

Volumn 46, Issue 29, 2007, Pages 5554-5558

  Shi, Zhangjie ^a,b   Li, Bijie ^b   Wan, Xiaobing ^b   Cheng, Jiang ^b,c   Fang, Zhao ^b   Cao, Bin ^b   Qin, Changming ^c   Wang, Yang ^b  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b PEKING UNIVERSITY   (China)

^c WENZHOU UNIVERSITY   (China)

Author keywords

C C coupling; C H activation; Electrophilic substitution; Palladium; Suzuki Miyaura reaction

Indexed keywords

AMINO ACIDS; CATALYST ACTIVITY; PALLADIUM; SUBSTITUTION REACTIONS;

C-C COUPLING; C-H ACTIVATION; ELECTROPHILIC SUBSTITUTION; SUZUKI-MIYAURA REACTION;

CHEMICAL BONDS;

EID: 34547212729     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200700590     Document Type: Erratum

References (79)

1. a) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457;
2. b) N. Miyaura, J. Organomet. Chem. 2002, 653, 54;
3. c) N. Miyaura, Top. Curr. Chem. 2002, 219, 11;
4. d) A. Suzuki, J. Organomet. Chem. 1999, 576, 147;
5. e) N. Miyaura, T. Ishiyama, M. Ishikawa, A. Suzuki, Tetrahedron Lett. 1986, 27, 6369;
6. f) S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. 2001, 113, 4676;
7. Angew. Chem. Int. Ed. 2001, 40, 4544;
8. g) K. C. Nicolaou, G. E. A. Carenzi, V. Jeso, Angew. Chem. 2005, 117, 3963;
9. Angew. Chem. Int. Ed. 2005, 44, 4442.
10. a) A. F. Littke, G. C. Fu. Angew. Chem. 2002, 114, 4350;
11. Angew. Chem. Int. Ed. 2002, 41, 4176;
12. b) D. W. Old, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc. 1998, 120, 9722-9723;
13. c) A. F. Littke, C. Dai, G. C. Fu, J. Am. Chem. Soc. 2000, 122, 4020;
14. d) J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550;
15. e) Q.-S. Hu, Y. Lu, Z.-Y. Tang, H.-B. Yu, J. Am. Chem. Soc. 2003, 125, 2856;
16. f) C. Nájera, J. Gil-Moltó, S. Karlström, Adv. Synth. Catal. 2004, 346, 1798;
17. g) R. B. Bedford, C. S. J. Cazin, S. L. Hazelwood, Angew. Chem. 2002, 114, 4294;
18. Angew. Chem. Int. Ed. 2002, 41, 4120;
19. h) J. H. Kirchhoff, C. Dai, G. C. Fu, Angew. Chem. 2002, 114, 2025;
20. Angew. Chem. Int. Ed. 2002, 41, 1945;
21. i) C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck, M. Grosche, W. A. Herrmann, Angew. Chem. 2002, 114, 1421;
22. Angew. Chem. Int. Ed. 2002, 41, 1363;
23. j) A. F. Littke, G. C. Fu, Angew. Chem. 1998, 110, 3586;
24. Angew. Chem. Int. Ed. 1998, 37, 3387.
25. For reviews, see: a) G. Dyker, Handbook of C-H Transformations. Applications in Organic Synthesis, Wiley-VCH, Weinheim, 2005;
26. b) S. Murai, Activation of Unreactive Bonds and Organic Synthesis. Springer, Berlin, 1999, pp. 48-78;
27. c) R. H. Crabtree, J. Organomet. Chem. 2004, 689;
28. d) A. E. Shilov, G. B. Shul'pin, Chem. Rev. 1997, 97, 2879 and references therein;
29. e) L. Shi, Y.-Q. Tu, M. Wang, F.-M. Zhang, C.-A. Fan, Y.-M. Zhao, W.-J. Xia, J. Am. Chem. Soc. 2005, 127, 10 836;
30. f) N. Chatani, T. Asaumi, S. Yorimitsu, T. Ikeda, F. Kakiuchi, S. Murai, Nature 1993, 366, 529;
31. g) H. Y. Chen, S. Schlecht, T. C. Semple, J. F. Hartwig, Science 2000, 287, 1995;
32. h) M. Lin, C. Shen, E. A. Garcia-Zayas, A. Sen, J. Am. Chem. Soc. 2001, 123, 1000;
33. i) B. D. Dangel, J. A. Johnson, D. Sames, J. Am. Chem. Soc. 2001, 123, 8149;
34. j) Z. Li, C.-J. Li, J. Am. Chem. Soc. 2004, 126, 11 810;
35. k) H. Cheng, L. Gan, Y. Shi, X. Wei, J. Org. Chem. 2001, 66, 6369;
36. l) A. F. Heyduk, T. G. Driver, J. A. Labinger, J. E. Bercaw, J. Am. Chem. Soc. 2004, 126, 15 034;
37. m) H. M. L. Davies, Q. Jin, P. Ren, A. Y. Kovalenvsky, J. Org. Chem. 2002, 67, 4165;
38. n) J. P. Collman, R. Boulatov, Inorg. Chem. 2001, 40, 2461.
39. a) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174;
40. b) J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651;
41. c) M. Catellani, E. Motti, F. Faccini, R. Ferraccioli, Pure Appl. Chem. 2005, 77, 1243;
42. d) D. Shabashov, O. Daugulis, Org. Lett. 2006, 8, 4947;
43. e) M. Lafrance, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 16 496;
44. f) S. E. Denmark, J. M. Kallemeyn, J. Am. Chem. Soc. 2006, 128, 15 958;
45. g) T. Schaub, M. Backes, U. Radius, J. Am. Chem. Soc. 2006, 128, 15 964;
46. h) B. S. Lane, M. A. Brown, D. Sames, J. Am. Chem. Soc. 2005, 127, 8050;
47. i) N. R. Deprez, D. Kalyani, A. Krause, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 4972;
48. j) L.-C. Campeau, M. Parisien, A. Jean, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 581;
49. k) Y. Terao, H. Wakui, M. Nomoto, T. Satoh, M. Miura, M. Nomura, J. Org. Chem. 2003, 68, 5236.
50. a) C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, Y. Fujiwara, Science 2000, 287, 1992;
51. b) X. Chen, J.-J. Li, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 78;
52. c) M. A. Campo, Q. Huang, T. Yao, Q. Tian, R. C. Larock, J. Am. Chem. Soc. 2003, 125, 11 506;
53. d) C. Bressy, D. Alberico, M. Lautens, J. Am. Chem. Soc. 2005, 127, 13 148;
54. e) E. J. Hennessy, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 12 084;
55. f) X. Wang, B. S. Lane, D. Sames, J. Am. Chem. Soc. 2005, 127, 4996;
56. g) D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330;
57. h) M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. deVries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586;
58. i) S. J. Tremont, H. U. Rahman, J. Am. Chem. Soc. 1984, 106, 5759;
59. j) V. G. Zaitsev, O. Daugulis, J. Am. Chem. Soc. 2005, 127, 4156.
60. a) X. Chen, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 12 634;
61. b) 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.
62. a) S. J. Pastine, D. V. Gribkov, D. Sames, J. Am. Chem. Soc. 2006, 128, 14 220;
63. b) N. Chatani, T. Asaumi, S. Yorimitsu, T. Ikeda, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2001, 123, 10 935;
64. c) N. Chatani, T. Asaumi, T. Ikeda, S. Yorimitsu, Y. Ishii, F. Kakiuchi, S. Murai, J. Am. Chem. Soc. 2000, 122, 12 882.
65. X. Wan, Z. Ma, B. Li, K. Zhang, S. Cao, S. Zhang, Z. Shi, J. Am. Chem. Soc. 2006, 128, 7416.
66. a) S. Punna, D. D. Diaz, M. G. Finn, Synlett 2004, 13, 2351;
67. b) N. Rodriguez, A. Cuenca, C. Ramirez de Arellano, M. Medio-Simon, D. Peine, G. Asensio, J. Org. Chem. 2004, 69, 8070.
68. J. Chen, A. Cammers-Goodwin, Tetrahedron Lett. 2003, 44, 1503.
69. a) K. Nishiura, Y. Urawa, S. Soda, Adv. Synth. Catal. 2004, 346, 1679;
70. b) Q. Li, T. Li, K. W. Woods, W.-Z. Gu, J. Cohen, V. S. Stoll, T. Galicia, C. Hutchins, D. Frost, S. H. Rosenberg, H. L. Sham, Bioorg. Med. Chem. Lett. 2005, 15, 2918;
71. c) E. A. Terefenko, J. Kern, A. Fensome, J. Wrobel, Y. Zhu, J. Cohen, R. Winneker, Z. Zhang, P. Zhang, Bioorg. Med. Chem. Lett. 2005, 15, 3600;
72. d) D. M. T. Chan, K. L. Monaco, R. Wang, M. P. Winters, Tetrahedron Lett. 1998, 39, 2933.
73. a) C. H. Yoon, K. S. Yoo, S. W. Yi, R. K. Mishra, K. W. Jung, Org. Lett. 2004, 6, 4037;
74. b) J. P. Parrish, Y. C. Jung, S. I. Shin, K. W. Jung, J. Org. Chem. 2002, 67, 7127;
75. c) J. H. Delcamp, C. M. White, J. Am. Chem. Soc. 2006, 128, 15 076.
76. D. J. Cardenas, B. Martin-Matute, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 5033.
77. V. V. Grushin, Organometallics 2000, 19, 1888.
78. a) D. L. Davies, S. M. A. Donald, S. A. Macgregor, J. Am. Chem. Soc. 2005, 127, 13 754;
79. b) D. Garcia-Cuadrado, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 1066.