Iron-mediated direct arylation of unactivated arenes

Angewandte Chemie - International Edition

Volumn 47, Issue 46, 2008, Pages 8897-8900

  Wen, Jun ^a   Zhang, Ji ^a   Chen, Shan Yong ^a   Li, Jing ^a   Yu, Xiao Qi ^a,b  

^a China   (China)

^b SICHUAN UNIVERSITY   (China)

Author keywords

Biaryls; Boronic acids; C H activation; Cross coupling; Iron

Indexed keywords

ACIDS; ACTIVATION ANALYSIS; CHEMICAL BONDS; CHEMICAL COMPOUNDS; CHEMICAL REACTIONS;

ARYLATION; BIARYL COMPOUNDS; BIARYLS; BORONIC ACIDS; C-H ACTIVATION; CHEMICAL EQUATIONS; CROSS COUPLINGS; CROSS-COUPLING; H BONDS; LOW TOXICITIES; OPTIMIZED REACTION CONDITIONS; PHENYLBORONIC ACIDS;

AROMATIC COMPOUNDS;

BORONIC ACID DERIVATIVE; IRON; ORGANIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

BORONIC ACIDS; IRON; MOLECULAR STRUCTURE; ORGANIC CHEMICALS;

EID: 57349174599     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200802526     Document Type: Article

References (96)

1. a) K. G. B. Torssell in Natural Product Chemistry, Wiley, Chichester, 1983;
2. b) R. H. Thomson in The Chemistry of Natural Products, Blackie, Glasgow, 1985;
3. c) J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359;
4. d) J. P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651.
5. a) Metal-Catalyzed Cross-Coupling Reactions (Eds.: A. de Meijere, F. Diederich), Wiley-VCH, Weinheim, 2004;
6. b) Transition Metals for Organic Synthesis (Eds.: M. Beller, C. Bolm), Wiley-VCH, New York, 2004.
7. a) P. Knochel, R. Singer, Chem. Rev. 1993, 93, 2117;
8. b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457;
9. c) N. Miyaura, Top. Curr. Chem. 2002, 219, 11;
10. d) A. F. Littke, L. Schwartz, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 6343;
11. e) S. E. Denmark, R. F. Sweis, Acc. Chem. Res. 2002, 35, 835;
12. f) A. H. Roy, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 8704.
13. a) D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174;
14. b) I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173.
15. a) T. Satoh, Y. Kametani, Y. Terao, M. Miura, M. Nomura, Angew. Chem. 1997, 109, 1820;
16. Angew. Chem. Int. Ed. Engl. 1997, 36, 1740;
17. b) T. Satoh, Y. Kametani, Y. Terao, M. Miura, M. Nomura, Tetrahedron Lett. 1999, 40, 5345;
18. c) L.-C. Campeau, M. Parisien, M. Leblanc, K. Fagnou, J. Am. Chem. Soc. 2004, 126, 9186;
19. d) O. Daugulis, V. G. Zaitsev, Angew. Chem. 2005, 117, 4114;
20. Angew. Chem. Int. Ed. 2005, 44, 4046;
21. e) D. Kalyani, N. R. Deprez, L. V. Desai, M. S. Sanford, J. Am. Chem. Soc. 2005, 127, 7330;
22. f) M. Lafrance, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 16496;
23. g) K. L. Hull, E. L. Lanni, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 14047;
24. h) H. A. Chiong, Q.-N. Pham, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 9879;
25. i) Y. Rong, R. Li, W. Lu, Organometallics 2007, 26, 4376;
26. j) Z. Shi, B. Li, X. Wan, J. Cheng, Z. Fang, B. Cao, C. Qin, Y. Wang, Angew. Chem. 2007, 119, 5650;
27. Angew. Chem. Int. Ed. 2007, 46, 5554;
28. k) B. Li, S. Tian, Z. Fang, Z. Shi, Angew. Chem. 2008, 120, 1131;
29. Angew. Chem. Int. Ed. 2008, 47, 1115;
30. l) H. Kawai, Y. Kobayashi, S. Oi, Y. Inoue, Chem. Commun. 2008, 1464.
31. a) S. Oi, S. Fukita, Y. Inoue, Chem. Commun. 1998, 2439;
32. b) R. B. Bedford, S. J. Coles, M. B. Hursthouse, M. E. Limmert, Angew. Chem. 2003, 115, 116;
33. Angew. Chem. Int. Ed. 2003, 42, 112;
34. c) R. B. Bedford, M. E. Limmert, J. Org. Chem. 2003, 68, 8669;
35. d) X. Wang, B. S. Lane, D. Sames, J. Am. Chem. Soc. 2005, 127, 4996;
36. e) S. Proch, R. Kempe, Angew. Chem. 2007, 119, 3196;
37. Angew. Chem. Int. Ed. 2007, 46, 3135;
38. f) R. B. Bedford, M. Betham, A. J. M. Caffyn, J. P. H. Charmant, L. C. L. -Alleyne, P. D. Long, D. P. -Cerón, S. Prashar, Chem. Commun. 2008, 990.
39. a) S. Oi, S. Fukita, N. Hirata, N. Watanuki, S. Miyano, Y. Inoue, Org. Lett. 2001, 3, 2579;
40. b) S. Oi, Y. Ogino, S. Fukita, Y. Inoue, Org. Lett. 2002, 4, 1783;
41. c) F. Kakiuchi, S. Kan, K. Igi, N. Chatani, S. Murai, J. Am. Chem. Soc. 2003, 125, 1698;
42. d) S. Oi, E. Aizawa, Y. Ogino, Y. Inoue, J. Org. Chem. 2005, 70, 3113;
43. e) F. Kakiuchi, Y. Matsuura, S. Kan, N. Chatani, J. Am. Chem. Soc. 2005, 127, 5936;
44. f) L. Ackermann, Org. Lett. 2005, 7, 3123;
45. g) L. Ackermann, A. Althammer, R. Born, Angew. Chem. 2006, 118, 2681;
46. Angew. Chem. Int. Ed. 2006, 45, 2619;
47. h) I. Ozdemir, S. Demir, B. Cetinkaya, C. Gourlaouen, F. Maseras, C. Bruneau, P. H. Dixneuf, J. Am. Chem. Soc. 2008, 130, 1156.
48. a) K. Fujita, M. Nonogawa, R. Yamaguchi, Chem. Commun. 2004, 1926;
49. b) H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 12404;
50. c) H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2008, 130, 1128;
51. d) A. Kar, N. Mangu, H. M. Kaiser, M. Beller, M. K. Tse, Chem. Commun. 2008, 386;
52. e) I. Ban, T. Sudo, T. Taniguchi, K. Itami, Org. Lett. 2008, 10, 3607.
53. For reviews see: a) C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217;
54. b) A. Correa, O. G. Mancheño, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108;
55. c) A. Fürstner, R. Martin, Chem. Lett. 2005, 34, 624;
56. d) B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, DOI: 10.1021/ar800039x.
57. a) M. Carril, A. Correa, C. Bolm, Angew. Chem. 2008, 120, 4940;
58. Angew. Chem. Int. Ed. 2008, 47, 4862;
59. b) A. Correa, C. Bolm, Angew. Chem. 2007, 119, 9018;
60. Angew. Chem. Int. Ed. 2007, 46, 8862;
61. c) A. Correa, S. Elmore, C. Bolm, Chem. Eur. J. 2008, 14, 3527;
62. d) O. Bistri, A. Correa, C. Bolm, Angew. Chem. 2008, 120, 596;
63. Angew. Chem. Int. Ed. 2008, 47, 586;
64. e) A. Correa, M. Carril, C. Bolm, Angew. Chem. 2008, 120, 2922;
65. Angew. Chem. Int. Ed. 2008, 47, 2880;
66. f) B. Scheiper, M. Bonnekessel, H. Krause, A. Fürstner, J. Org. Chem. 2004, 69, 3943;
67. g) R. Martin, A. Fürstner, Angew. Chem. 2004, 116, 4045;
68. Angew. Chem. Int. Ed. 2004, 43, 3955;
69. h) I. Sapountzis, W. Lin, C. C. Kofink, C. Despotopoulou, P. Knochel, Angew. Chem. 2005, 117, 1682;
70. Angew. Chem. Int. Ed. 2005, 44, 1654;
71. i) J. Kischel, I. Jovel, K. Metins, A. Zapf, M. Beller, Org. Lett. 2006, 8, 19;
72. j) K. Komeyama, T. Morimoto, K. Takaki, Angew. Chem. 2006, 118, 3004;
73. Angew. Chem. Int. Ed. 2006, 45, 2938;
74. k) C. C. Kofink, B. Blank, S. Pagano, N. Gotz, P. Knochel, Chem. Commun. 2007, 1954;
75. l) G. Anilkumar, B. Bitterlich, F. G. Gelalcha, M. K. Tse, M. Beller, Chem. Commun. 2007, 289;
76. m) H. Egami, T. Katsuki, J. Am. Chem. Soc. 2007, 129, 8940;
77. n) F. G. Gelalcha, B. Bitterlich, G. Anilkumar, M. K. Tse, M. Beller, Angew. Chem. 2007, 119, 7431;
78. Angew. Chem. Int. Ed. 2007, 46, 7293;
79. o) T. Hatakeyama, M. Nakamura, J. Am. Chem. Soc. 2007, 129, 9844;
80. p) G. Cahiez, C. Duplais, A. Moyeux, Org. Lett. 2007, 9, 3253;
81. q) R. Li, S. R. Wang, W. Lu, Org. Lett. 2007, 9, 2219.
82. a) J. Norinder, A. Matsumoto, N. Yoshikai, E. Nakamura, J. Am. Chem. Soc. 2008, 130, 5858;
83. b) X. Zhao, Z. Yu, J. Am. Chem. Soc. 2008, 130, 8136.
84. a) A. S. Demir, O. Reis, M. Emrullahoglu, J. Org. Chem. 2003, 68, 578;
85. b) M. M. S. Andappan, P. Nilsson, M. Larhed, Chem. Commun. 2004, 218;
86. c) P.-A. Enquist, J. Lindh, P. Nilsson, M. Larhed, Green Chem. 2006, 8, 338;
87. d) B. J. Gallon, R. W. Kojima, R. B. Kaner, P. L. Diaconescu, Angew. Chem. 2007, 119, 7389;
88. Angew. Chem. Int. Ed. 2007, 46, 7251;
89. e) C. Peng, Y. Wang, J. Wang, J. Am. Chem. Soc. 2008, 130, 1586;
90. f) C. Qin, H. Wu, J. Chen, M. Liu, J. Cheng, W. Su, J. Ding, Org. Lett. 2008, 10, 1537;
91. g) C. A. Fleckenstein, H. Plenio, Chem. Eur. J. 2008, 14, 4267.
92. a) R. Giri, X. Chen, J.-Q. Yu, Angew. Chem. 2005, 117, 2150;
93. Angew. Chem. Int. Ed. 2005, 44, 2112;
94. b) L.-C. Campeau, M. Parosien, A. Jean, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 581;
95. c) D. Garcia Cuadrado, P. Mendoza, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2007, 129, 6880;
96. d) J.-B. Xia, S.-L. You, Organometallics 2007, 26, 4869.