Palladium-catalyzed kumada coupling reaction of bromoporphyrins with silylmethyl grignard reagents: Preparation of silylmethyl-substituted porphyrins as a multipurpose synthon for fabrication of porphyrin systems

Journal of Organic Chemistry

Volumn 77, Issue 23, 2012, Pages 10488-10497

  Sugita, Noriaki ^a   Hayashi, Satoshi ^a   Hino, Fumio ^a   Takanami, Toshikatsu ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING REACTION; DOUBLE BONDS; GRIGNARD REAGENT; KUMADA CROSS-COUPLING; OXIDATIVE CONVERSION; PALLADIUM-CATALYZED; PORPHYRIN DERIVATIVES; SYNTHETIC UTILITY; SYNTHONS;

AUTOMOBILE MANUFACTURE; CATALYSIS;

PORPHYRINS;

10 (BENZYLDIMETHYLSILYL)METHYL 5,15 DIPHENYLPORPHYRIN; 10 (DIMETHYLPHENYLSILYL)METHYL 5,15 DIPHENYLPORPHYRIN; 10 BIS(TRIMETHYLSILYL)METHYL 5,15 DIPHENYLPORPHYRIN; 10,20 BIS(TRIMETHYLSILYL)METHYL 5,15 DIPHENYLPORPHYRIN; 10,20 DIPHENYL 5 HYDROXYMETHYLPORPHYRIN; 10,20 DIPHENYL 5 METHOXYMETHYLPORPHYRIN; 5 (TRIMETHYLSILYL)METHYL 10,15,20 TRIPHENYLPORPHYRIN; 5 [(2 FURAN 2 YL) 2 HYDRYOXYETHYL] 10,20 DIPHENYLPORPHYRIN; 5 FORMYL 10,20 DIPHENYLPORPHYRIN; 5,10,15,20 TETRAPHENYL 2 (TRIMETHYLSILYL)METHYLPORPHYRIN; 5,15 BIS (2,4,6 TRIMETHYLPHENYL) 10 (TRIMETHYLSILYL)METHYLPORPHYRIN; 5,15 BIS (3 METHOXYPHENYL) 10 (TRIMETHYLSILYL)METHYLPORPHYRIN; 5,15 BIS (3 VINYLPHENYL) 10 (TRIMETHYLSILYL)METHYLPORPHYRIN; 5,15 BIS[4 [2 (TRIISOPROPYLSILYL)ETHYNYL]PHENYL] 10 (TRIMETHYLSILYL)METHYLPORPHYRIN; 5,15 DI (4 TOLYL) 10 (TRIMETHYLSILYL)METHYLPORPHYRIN; 5,15 DI(N BUTYL) 10 (TRIMETHYLSILYL)METHYLPORPHYRIN; 5,15 DIFORMYL 10,20 DIPHENYLPORPHYRIN; 5,15 DIPHENYL 10 (ISOPROPOXYLDIMETHYLSILYL)METHYLPORPHYRIN; 5,15 DIPHENYL 10 (TRIETHYLSILYL)METHYLPORPHYRIN; 5,15 DIPHENYL 10 (TRIISOPROPYLSILYL)METHYLPORPHYRIN; 5,15 DIPHENYL 10 (TRIMETHYLSILYL)METHYLPORPHYRIN; 5,15 DIPHENYL 10 (TRIPHENYLSILYL)METHYLPORPHYRIN; 5,15 DIPHENYL 10 FLUOROMETHYLPORPHYRIN; 5,15 DIPHENYL 5 (3 METHOXYCARBONYLPROPYL)PORPHYRIN; GRIGNARD REAGENT; MAGNESIUM; NICKEL; PALLADIUM COMPLEX; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CATALYSIS; COMPLEX FORMATION; CROSS COUPLING REACTION; DESILYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; KUMADA CROSS COUPLING REACTION; OLEFINATION; ONE POT SYNTHESIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION;

CATALYSIS; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; PALLADIUM; PORPHYRINS;

EID: 84870879744     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302122f     Document Type: Article

References (74)

1. For a review, see: The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, 1999a-2003; Vol. 1a-20.
2. Fujiwara, K.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2012, 134, 5512-5515
3. Cong, Z.; Kurahashi, T.; Fujii, H. J. Am. Chem. Soc. 2012, 134, 4469-4472
4. Ozawa, T.; Kurahashi, T.; Matsubara, S. Org. Lett. 2012, 14, 3008-3011
5. Xu, X.; Lu, H.; Ruppel, J. V.; Cui, X.; Lopez de Mesa, S.; Wojtas, L.; Zhang, X. P. J. Am. Chem. Soc. 2011, 133, 15292-15295
6. Morandi, B.; Cheang, J.; Carreira, E. M. Org. Lett. 2011, 13, 3080-3081
7. Usanov, D. L.; Yamamoto, H. J. Am. Chem. Soc. 2011, 133, 1286-1289
8. Usanov, D. L.; Yamamoto, H. Angew. Chem., Int. Ed. 2010, 49, 8169-8172
9. Morandi, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2010, 49, 938-941
10. Che, C.-M.; Huang, J.-S. Chem. Commun. 2009, 3996-4015
11. Suda, K.; Nakajima, S.; Satoh, Y.; Takanami, T. Chem. Commun. 2009, 1255-1257
12. Jintoku, H.; Takafuji, M.; Oda, R.; Ihara, H. Chem. Commun. 2012, 48, 4881-4883
13. Zhang, J.; Li, Y.; Yang, W.; Lai, S.-W.; Zhou, C.; Liu, H.; Che, C.-M.; Li, Y. Chem. Commun. 2012, 48, 3602-3604
14. Liang, Q.-F.; Liu, J.-J.; Chen, J. Tetrahedron Lett. 2011, 52, 3987-3991
15. Berova, N.; Pescitelli, G.; Petrovica, A. G.; Pronic, G. Chem. Commun. 2009, 5958-5980
16. Hembury, G. A.; Borovkov, V. V.; Inoue, Y. Chem. Rev. 2008, 108, 1-73
17. Thomas, A. P.; Babu, P. S. S.; Nair, S. A.; Ramakrishnan, S.; Ramaiah, D.; Chandrashekar, T. K.; Srinivasan, A.; Pillai, M. R. J. Med. Chem. 2012, 55, 5110-5120
18. Hsu, C.-Y.; Nieh, M.-P.; Lai, P.-S. Chem. Commun. 2012, 48, 9343-9345
19. Ethirajan, M.; Chen, Y.; Joshi, P.; Pandey, R. K. Chem. Soc. Rev. 2011, 40, 340-362
20. Verma, S.; Ghosh, H. N. J. Phys. Chem. Lett. 2012, 3, 1877-1884
21. Diev, V. V.; Schlenker, C. W.; Hanson, K.; Zhong, Q.; Zimmerman, J. D.; Forrest, S. R.; Thompson, M. E. J. Org. Chem. 2012, 77, 143-159
22. Matano, Y.; Matsumoto, K.; Hayashi, H.; Nakao, Y.; Kumpulainen, T.; Chukharev, V.; Tkachenko, N. V.; Lemmetyinen, H.; Shimizu, S.; Kobayashi, N.; Sakamaki, D.; Ito, A.; Tanaka, K.; Imahori, H. J. Am. Chem. Soc. 2012, 134, 1825-1839
23. Hasobe, T.; Sakai, H. J. Porphyrins Phthalocyanines 2011, 15, 301-311
24. Ribó, J. M. Angew. Chem., Int. Ed. 2011, 50, 12402-12404
25. Senge, M. O. Chem. Commun. 2011, 47, 1943-1960
26. Shinokubo, H.; Osuka, A. Chem. Commun. 2009, 1011-1021 and selected examples, see refs 7-9
27. Peng, X.; Gao, C.; Huang, Y.; Peng, J.; Aratani, N.; Osuka, A. Tetrahedron Lett. 2012, 53, 1156-1159
28. Anabuki, S.; Tokuji, S.; Aratani, N.; Osuka, A. Org. Lett. 2012, 14, 2778-2781
29. Akita, M.; Hiroto, S.; Shinokubo, H. Angew. Chem., Int. Ed. 2012, 51, 2894-2897
30. Yamashita, K.; Kataoka, K.; Asano, M. S.; Sugiura, K. Org. Lett. 2012, 14, 190-193
31. Senge, M. O.; Ryppa, C.; Fazekas, M.; Zawadzka, M.; Dahms, K. Chem.î-̧Eur. J. 2011, 17, 13562-13573
32. Takanami, T.; Hayashi, M.; Hino, F.; Suda, K. Tetrahedron Lett. 2003, 44, 7353-7357
33. Takanami, T.; Hayashi, M.; Chijimatsu, H.; Inoue, W.; Suda, K. Org. Lett. 2005, 7, 3937-3940
34. Takanami, T.; Yotsukura, M.; Inoue, W.; Inoue, N.; Hino, F.; Suda, K. Heterocycles 2008, 76, 439-453
35. Takanami, T.; Wakita, A.; Sawaizumi, A.; Iso, K.; Onodera, H.; Suda, K. Org. Lett. 2008, 10, 685-687
36. Takanami, T.; Wakita, A.; Matsumoto, J.; Sekine, S.; Suda, K. Chem. Commun. 2009, 101-103
37. Takanami, T.; Matsumoto, J.; Kumagai, Y.; Sawaizumi, A.; Suda, K. Tetrahedron Lett. 2009, 50, 68-70
38. Takanami, T.; Hayashi, S.; Iso, K.; Matsumoto, J.; Hino, F. Tetrahedron Lett. 2011, 52, 5345-5348
39. Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; Wiley, New York, 2000.
40. Hosomi, A.; Miura, K. Bull. Chem. Soc. Jpn. 2004, 77, 835-851
41. Handbook of Reagents for Organic Synthesis: Reagents for Silicon-Mediated Organic Synthesis; Fuchs, P. L., Ed.; Wiley: Chichester, 2011.
42. Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901-6905
43. Itami, K.; Kamei, T.; Yoshida, J. J. Am. Chem. Soc. 2001, 123, 8773-8779
44. Staden, L. F.; Gravestock, D.; Ager, D. J. Chem. Soc. Rev. 2002, 31, 195-200
45. Davies, I. W.; Smitrovich, J. H.; Sidler, R.; Qu, C.; Gresham, V.; Bazaral, C. Tetrahedron 2005, 61, 6425-6437
46. Zhang, W.-X.; Ding, C.-H.; Luo, Z.-B.; Houa, X.-L.; Dai, L.-X. Tetrahedron Lett. 2006, 47, 8391-8393
47. Mita, T.; Michigami, K.; Sato, Y. Org. Lett. 2012, 14, 3462-3465
48. van den Ancker, T. R.; Raston, C. L.; Skelton, B. W.; White, A. H. Organometallics 2000, 19, 4437-4444
49. Ekici, S.; Gudat, D.; Nieger, M.; Nyulaszi, L.; Niecke, E. Angew. Chem., Int. Ed. 2002, 41, 3368-3371
50. Wang, Li.; Zhang, C.; Wang, Z.-X. Eur. J. Inorg. Chem. 2007, 2477-2487
51. Yoshida, J.; Kataoka, K.; Horcajada, R.; Nagaki, A. Chem. Rev. 2008, 108, 2265-2299
52. Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599-7662
53. Colvin, E. W. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, pp 641-651.
54. Oxidative carbon-carbon bond formation of silylmethyl-substituted arenes with olefins has recently been reported, see: Montanaro, S.; Ravelli, D.; Merli, D.; Fagnoni, M.; Albini, A. Org. Lett. 2012, 14, 4218-4221
55. Wang, C.; Ge, H. Chem.î-̧Eur. J. 2011, 17, 14371-14374
56. Huang, C.; Ghavtadze, N.; Godoi, B.; Gevorgyan, V. Chem.î- ̧Eur. J. 2012, 18, 9789-9792
57. For a recent review on transition metal-catalyzed cross-coupling reactions using alkyl-organometallics, including Grignard reagents, as reaction partners, see: Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417-1492
58. For a review on the preparation and reactivity of silylmethyl Grignard reagents, see: Ager, D. J.; Yorimitsu, H.; Oshima, K. In Handbook of Reagents for Organic Synthesis: Reagents for Silicon-Mediated Organic Synthesis; Fuchs, P. L., Ed.; Wiley: Chichester, 2011; pp 666-674.
59. Preparation of (chloromethyl)silanes, see: Kobayashi, T.; Pannell, K. H. Organometallics 1991, 10, 1960-1964
60. Preparation of silylmethyl Grignard reagents, see: Lam, Y.-h.; Bobbio, C.; Cooper, I. R.; Gouverneur, V. Angew. Chem., Int. Ed. 2007, 46, 5106-5110
61. Recently, Osuka, Shinokubo, and co-workers reported the unprecedented use of palladium catalysts for promoting dehalogenative homocouplings of meso-bromoporphyrins, see: Tokuji, S.; Yurino, T.; Aratani, N.; Shinokubo, H.; Osuka, A. Chem.î-̧Eur. J. 2009, 15, 12208-12211
62. Organ, M. G.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; OBrien, C. J.; Valente, C. Chem.î-̧Eur. J. 2006, 12, 4749-4755
63. Organ, M. G.; Abdel-Hadi, M.; Avola, S.; Hadei, N.; Nasielski, J.; OBrien, C. J.; Valente, C. Chem.î-̧Eur. J. 2007, 13, 150-157
64. Manolikakes, G.; Knochel, P. Angew. Chem., Int. Ed. 2009, 48, 205-209
65. Ackermann, L.; Born, R.; Spatz, J. H.; Meyer, D. Angew. Chem., Int. Ed. 2005, 44, 7216-7219
66. Ackermann, L.; Althammer, A. Org. Lett. 2006, 8, 3457-3460
67. Wolf, C.; Xu, H. J. Org. Chem. 2008, 73, 162-167
68. Ackermann, L.; Potukuchi, H. K.; Kapdi, A. R.; Schulzke, C. Chem.î-̧Eur. J. 2010, 16, 3300-3303
69. Williams, D. R.; Morales-Ramos, Á. I.; Williams, C. M. Org. Lett. 2006, 8, 4393-4396
70. Balakumar, A.; Muthukumaran, K.; Lindsey, J. S. J. Org. Chem. 2004, 69, 5112-5115
71. Senge, M. O.; Hatscher, S. S.; Wiehe, A.; Dahms, K.; Kelling, A. J. Am. Chem. Soc. 2004, 126, 13634-13635
72. Dahms, K.; Senge, M. O.; Bakar, M. B. Eur. J. Org. Chem. 2007, 3833-3848 and references cited therein
73. Kano, N.; Kawashima, T. In Modern Carbonyl Olefination; Takeda, T., Ed.; Wiley-VCH: Weinheim, 2004; pp 18-103.
74. Palomo, C.; Aizpurua, J. M.; Garcia, J. M.; Ganboa, I.; Cossio, F. P.; Lecea, B.; López, C. J. Org. Chem. 1990, 55, 2498-2503