Palladium-catalyzed β-selective direct arylation of porphyrins

Angewandte Chemie - International Edition

Volumn 50, Issue 38, 2011, Pages 8867-8870

  Kawamata, Yu ^a   Tokuji, Sumito ^a   Yorimitsu, Hideki ^a   Osuka, Atsuhiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

arylation; C H activation; palladium; porphyrinoids

Indexed keywords

ACID SYSTEMS; ARYL BROMIDES; ARYLATIONS; C-H ACTIVATION; EFFICIENT METHOD; PALLADIUM CATALYST; PORPHYRINOIDS; PREFUNCTIONALIZATION;

ACTIVATION ANALYSIS; BROMINE COMPOUNDS; CHEMICAL REACTIONS; PORPHYRINS;

AROMATIC COMPOUNDS;

EID: 80052581248     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201102318     Document Type: Article

References (72)

1. The Porphyrin Handbook, Vol. 6 (Eds:, K. M. Kadish, K. M. Smith, R. Guilard,), Academic Press, San Diego, 2000
2. Handbook of Porphyrin Science, Vol. 1 (Eds:, K. M. Kadish, K. M. Smith, R. Guilard,), World Scientific Publishing, Singapore, 2010
3. M. V. Martínez-Díaz, G. de La Torre, T. Torres, Chem. Commun. 2010, 46, 7090
4. D. Gust, T. A. Moore, A. L. Moore, Acc. Chem. Res. 2009, 42, 1890
5. M. O. Senge, M. Fazekas, E. G. A. Notaras, W. J. Blau, M. Zawadzka, O. B. Locos, E. M. N. Mhuircheartaigh, Adv. Mater. 2007, 19, 2737
6. M. Ethirajan, Y. Chen, P. Joshi, R. K. Pandey, Chem. Soc. Rev. 2011, 40, 340
7. T. Hori, Y. Nakamura, N. Aratani, A. Osuka, J. Organomet. Chem. 2007, 692, 148
8. N. Aratani, D. Kim, A. Osuka, Acc. Chem. Res. 2009, 42, 1922
9. N. Aratani, D. Kim, A. Osuka, Chem. Asian J. 2009, 4, 1172
10. M. R. Wasielewski, Acc. Chem. Res. 2009, 42, 1910.
11. The Porphyrin Handbook, Vol. 1 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), Academic Press, San Diego, 2000
12. Handbook of Porphyrin Science, Vol. 2 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), World Scientific Publishing, Singapore, 2010. For recent reviews, see
13. M. O. Senge, Chem. Commun. 2011, 47, 1943
14. M. O. Senge, Y. M. Shaker, M. Pintea, C. Ryppa, S. S. Hatscher, A. Ryan, Y. Sergeeva, Eur. J. Org. Chem. 2010, 237
15. H. Shinokubo, A. Osuka, Chem. Commun. 2009, 1011
16. T. Ren, Chem. Rev. 2008, 108, 4185
17. B. M. J. M. Suijkerbuijk, R. J. M. Klein Gebbink, Angew. Chem. 2008, 120, 7506
18. Angew. Chem. Int. Ed. 2008, 47, 7396
19. F. Atefi, D. P. Arnold, J. Porphyrins Phthalocyanines 2008, 12, 801.
20. M. O. Senge, W. W. Kalisch, I. Bischoff, Chem. Eur. J. 2000, 6, 2721
21. M. O. Senge, X. Feng, J. Chem. Soc. Perkin Trans. 1 2000, 3615.
22. Cross-Coupling Reactions: A Practical Guide (Ed.:, N. Miyaura,), Springer, Heidelberg, 2010
23. Metal-Catalyzed Cross-Coupling Reactions (Eds.:, A. de Meijere, F. Diederich,), Wiley, Weinheim, 2004.
24. N. N. Sergeeva, M. O. Senge, A. Ryan, in Handbook of Porphyrin Science, Vol. 3 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), World Scientific Publishing, Singapore, 2010, chap. 13
25. J. E. Van Lier, W. M. Sharman, J. Porphyrins Phthalocyanines 2000, 4, 441.
26. J. A. S. Cavaleiro, A. C. Tomé, M. G. P. M. S. Neves, in Handbook of Porphyrin Science, Vol. 2 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), World Scientific Publishing, Singapore, 2010, chap. 9
27. L. Jaquinod, in The Porphyrin Handbook, Vol. 1 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), Academic Press, San Diego, 2000, chap. 5
28. M. O. Senge, in The Porphyrin Handbook, Vol. 1 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), Academic Press, San Diego, 2000, chap. 6.
29. For pioneering work on sequential halogenation/metalation/cross-coupling with porphyrins, see:, A. G. Hyslop, M. A. Kellett, P. M. Iovine, M. J. Therien, J. Am. Chem. Soc. 1998, 120, 12676. For reviews, see reference [2f-h].
30. H. Hata, H. Shinokubo, A. Osuka, J. Am. Chem. Soc. 2006, 128, 4119
31. H. Hata, S. Yamaguchi, G. Mori, S. Nakazono, T. Katoh, K. Takatsu, S. Hiroto, H. Shinokubo, A. Osuka, Chem. Asian J. 2007, 2, 849
32. S. Yamaguchi, T. Katoh, H. Shinokubo, A. Osuka, J. Am. Chem. Soc. 2007, 129, 6392
33. S. Yamaguchi, T. Katoh, H. Shinokubo, A. Osuka, J. Am. Chem. Soc. 2008, 130, 14440
34. J. Song, N. Aratani, H. Shinokubo, A. Osuka, J. Am. Chem. Soc. 2010, 132, 16356.
35. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174
36. T. Satoh, M. Miura, Chem. Lett. 2007, 36, 200
37. A. Mori, A. Sugie, Bull. Chem. Soc. Jpn. 2008, 81, 548
38. T. Satoh, M. Miura, Synthesis 2010, 3395
39. L. Ackermann, R. Vicente, A. R. Kapdi, Angew. Chem. 2009, 121, 9976
40. Angew. Chem. Int. Ed. 2009, 48, 9792
41. D. Lapointe, K. Fagnou, Chem. Lett. 2010, 39, 1118
42. K. Hirano, M. Miura, Synlett 2011, 294
43. C-H Activation (Eds.:, J.-Q. Yu, Z. Shi,), Springer, Heidelberg, 2010
44. I. V. Seregin, V. Gevorgyan, Chem. Soc. Rev. 2007, 36, 1173
45. O. Daugulis, V. G. Zaitsev, D. Shabashov, Q.-N. Pham, A. Lazareva, Synlett 2006, 3382.
46. M. Lafrance, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 16496
47. X. Wang, D. V. Gribkov, D. Sames, J. Org. Chem. 2007, 72, 1476
48. J. Norinder, A. Matsumoto, N. Yoshikai, E. Nakamura, J. Am. Chem. Soc. 2008, 130, 5858
49. K. Kitazawa, T. Kochi, M. Sato, F. Kakiuchi, Org. Lett. 2009, 11, 1951
50. M. Tobisu, I. Hyodo, N. Chatani, J. Am. Chem. Soc. 2009, 131, 12070
51. J. Canivet, J. Yamaguchi, I. Ban, K. Itami, Org. Lett. 2009, 11, 1733
52. A. M. Wagner, M. S. Sanford, Org. Lett. 2011, 13, 288
53. E. T. Nadres, A. Lazareva, O. Daugulis, J. Org. Chem. 2011, 76, 471
54. M. J. Tredwell, M. Gulias, N. G. Bremeyer, C. C. C. Johansson, B. S. L. Collins, M. J. Gaunt, Angew. Chem. 2011, 123, 1108
55. Angew. Chem. Int. Ed. 2011, 50, 1076
56. D. García-Cuadrado, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 1066.
57. For our previous work, see:, M. Iwasaki, H. Yorimitsu, K. Oshima, Chem. Asian J. 2007, 2, 1430.
58. F. Shibahara, E. Yamaguchi, T. Murai, Chem. Commun. 2010, 46, 2471
59. T. Satoh, M. Miura, M. Nomura, J. Organomet. Chem. 2002, 653, 161
60. T. Okazawa, T. Satoh, M. Miura, M. Nomura, J. Am. Chem. Soc. 2002, 124, 5286
61. I. Ban, T. Sudo, T. Tanoguchi, K. Itami, Org. Lett. 2008, 10, 3607
62. D. Shabashov, O. Daugulis, Org. Lett. 2006, 8, 4947
63. S. Oi, S. Fukita, N. Hirata, N. Watanuki, S. Miyano, Y. Inoue, Org. Lett. 2001, 3, 2579
64. J.-M. Joo, B. B. Toure, D. Sames, J. Org. Chem. 2010, 75, 4911
65. S. Nakazono, S. Easwaramoorthi, D. Kim, H. Shinokubo, A. Osuka, Org. Lett. 2009, 11, 5426
66. T. Satoh, Y. Kawamura, M. Miura, M. Nomura, Angew. Chem. 1997, 109, 1820
67. Angew. Chem. Int. Ed. Engl. 1997, 36, 1740.
68. S. Suga, D. Yamada, J. Yoshida, Chem. Lett. 2010, 39, 404, and references therein
69. A. J. Bard, Integrated Chemical Systems, Wiley, New York, 1994
70. Multicomponent Reactions (Eds.:, J. Zhu, H. Bienaymé,), Wiley, Weinheim, 2005.
71. S. I. Gorelsky, D. Lapointe, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 10848.
72. K. M. Kadish, M. M. Morrison, Inorg. Chem. 1976, 15, 980.