Modular synthesis of triarylmethanes through palladium-catalyzed sequential arylation of methyl phenyl sulfone

Angewandte Chemie - International Edition

Volumn 53, Issue 3, 2014, Pages 742-746

  Nambo, Masakazu ^a   Crudden, Cathleen M ^a,b  

^a NAGOYA UNIVERSITY   (Japan)

^b QUEEN S UNIVERSITY   (Canada)

Author keywords

C H activation; N heterocyclic carbenes; palladium; sulfones; Suzuki Miyaura coupling

Indexed keywords

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; CATALYSIS;

ARYL BORONIC ACIDS; C-H ACTIVATION; MODULAR SYNTHESIS; N-HETEROCYCLIC CARBENES; PALLADIUM-CATALYZED; SULFONES; SUZUKI-MIYAURA COUPLING; SYNTHETIC APPROACH;

PALLADIUM;

ANTINEOPLASTIC AGENT; BORONIC ACID DERIVATIVE; CARBENE; CARBON; DIMETHYL SULFONE; DIMETHYL SULFOXIDE; DRUG DERIVATIVE; HYDROGEN; METHANE; PALLADIUM; SULFONE;

ARTICLE; C H ACTIVATION; CATALYSIS; CHEMISTRY; N-HETEROCYCLIC CARBENES; SUZUKI-MIYAURA COUPLING; SYNTHESIS;

C H ACTIVATION; N-HETEROCYCLIC CARBENES; PALLADIUM; SULFONES; SUZUKI-MIYAURA COUPLING;

ANTINEOPLASTIC AGENTS; BORONIC ACIDS; CARBON; CATALYSIS; DIMETHYL SULFOXIDE; HYDROGEN; METHANE; PALLADIUM; SULFONES;

EID: 84891884842     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201307019     Document Type: Article

References (74)

1. D. F. Duxbury, Chem. Rev. 1993, 93, 381
2. M. S. Shchepinov, V. A. Korshun, Chem. Soc. Rev. 2003, 32, 170
3. V. Nair, S. Thomas, S. C. Mathew, K. G. Abhilash, Tetrahedron 2006, 62, 6731.
4. C. D. Mason, F. F. Nord, J. Org. Chem. 1951, 16, 722
5. V. V. Ghaisas, B. J. Kane, F. F. Nord, J. Org. Chem. 1958, 23, 560
6. M. Irie, J. Am. Chem. Soc. 1983, 105, 2078
7. R. Muthyala, A. R. Katritzky, X. F. Lan, Dyes Pigm. 1994, 25, 303.
8. T. Miura, Y. Urano, K. Tanaka, T. Nagano, K. Ohkubo, S. Fukuzumi, J. Am. Chem. Soc. 2003, 125, 8666
9. R. P. Haugland, The Handbook. A Guide to Fluorescent Probes and Labeling Technologies, 10 th ed., Molecular Probes, Eugene, OR, USA, 2005
10. Y. Urano, M. Kamiya, K. Kanada, T. Ueno, K. Hirose, T. Nagano, J. Am. Chem. Soc. 2005, 127, 4888
11. H. Abe, J. Wang, K. Furukawa, K. Oki, M. Uda, S. Tsuneda, Y. Ito, Bioconjugate Chem. 2008, 19, 1219
12. H. N. Kim, M. H. Lee, H. J. Kim, J. S. Kim, J. Yoon, Chem. Soc. Rev. 2008, 37, 1465
13. M. Beija, C. A. M. Afonso, J. M. G. Martinho, Chem. Soc. Rev. 2009, 38, 2410
14. A. C. Bhasikuttan, J. Mohanty, W. M. Nau, H. Pal, Angew. Chem. 2007, 119, 4198
15. Angew. Chem. Int. Ed. 2007, 46, 4120.
16. R. D. Bindal, J. T. Golab, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1990, 112, 7861
17. L. Bai, N. Masukawa, M. Yamaki, S. Takagi, Phytochemistry 1998, 47, 1637
18. C. Jin, R. G. Michetich, M. Daneshtalab, Phytochemistry 1999, 50, 505
19. K. Baba, K. Maeda, Y. Tabata, M. Doi, M. Kozawa, Chem. Pharm. Bull. 1988, 36, 2977.
20. H. Jendralla, E. Granzer, B. Von Kerekjarto, R. Krause, U. Schacht, E. Baader, W. Bartman, G. Beck, A. Bergmann, K. Kesseler, G. Wess, L.-J. Chen, S. Granata, J. Herchen, H. Kleine, H. Schüssler, K. Wager, J. Med. Chem. 1991, 34, 2962
21. P. Wang, J. Kozlowski, M. Cushman, J. Org. Chem. 1992, 57, 3861
22. N. Mibu, K. Yokomizo, M. Uyeda, K. Sumoto, Chem. Pharm. Bull. 2003, 51, 1325
23. R. A. Al-Qawasmeh, Y. Lee, M.-Y. Cao, X. Gu, A. Vassilakos, J. A. Wright, A. Young, Bioorg. Med. Chem. Lett. 2004, 14, 347
24. R. Palchaudhuri, V. Nesterenko, P. J. Hergenrother, J. Am. Chem. Soc. 2008, 130, 10274
25. M. Y. Cao, Y. Lee, N. P. Feng, R. A. Al-Qawasmeh, S. Viau, X. P. Gu, L. Lau, H. Jin, M. Wang, A. Vassilakos, J. A. Wright, A. H. Young, J. Pharmacol. Exp. Ther. 2004, 308, 538.
26. J. Esquivias, R. G. Arrayás, J. C. Carretero, Angew. Chem. 2006, 118, 645
27. Angew. Chem. Int. Ed. 2006, 45, 629
28. P. Thirupathi, S. S. Kim, J. Org. Chem. 2009, 74, 7755
29. G. K. S. Prakash, C. Panja, A. Shakhmin, E. Shah, T. Mathew, G. A. Olah, J. Org. Chem. 2009, 74, 8659
30. S. Lin, X. Lu, J. Org. Chem. 2007, 72, 9757
31. P. Thirupathi, S. S. Kim, Eur. J. Org. Chem. 2010, 1798
32. P. Thirupathi, S. S. Kim, J. Org. Chem. 2010, 75, 5240
33. P. Thirupathi, L. N. Neupane, K.-H. Lee, Tetrahedron 2011, 67, 7301.
34. A. Ono, N. Suzuki, J. Kamimura, Synthesis 1987, 736
35. T. J. Mizoguchi, S. J. Lippard, J. Am. Chem. Soc. 1998, 120, 11022
36. V. Gevorgyan, M. Rubin, S. Benson, J.-X. Liu, Y. Yamamoto, J. Org. Chem. 2000, 65, 6179
37. R. Rathore, C. L. Burns, I. A. Guzei, J. Org. Chem. 2004, 69, 1524
38. S. Sawadjoon, A. Lundstedt, J. S. M. Samec, ACS Catal. 2013, 3, 635.
39. J.-Y. Yu, R. Kuwano, Org. Lett. 2008, 10, 973
40. A. Lõpez-Pérez, J. Adrio, J. C. Carretero, Org. Lett. 2009, 11, 5514
41. L.-L. Cao, X.-N. Li, F.-Y. Meng, G.-F. Jiang, Tetrahedron Lett. 2012, 53, 3873
42. Y. Xia, F. Hu, Z. Liu, P. Qu, R. Ge, C. Ma, Y. Zhang, J. Wang, Org. Lett. 2013, 15, 1784; for metal-catalyzed C-H arylations, see
43. T. Niwa, H. Yorimitsu, K. Oshima, Org. Lett. 2007, 9, 2373
44. Y.-Z. Li, B.-J. Li, X.-Y. Lu, S. Lin, Z.-J. Shi, Angew. Chem. 2009, 121, 3875
45. Angew. Chem. Int. Ed. 2009, 48, 3817
46. G. I. McGrew, J. Temaismithi, P. J. Carroll, P. J. Walsh, Angew. Chem. 2010, 122, 5673
47. Angew. Chem. Int. Ed. 2010, 49, 5541
48. J. Zhang, A. Bellomo, A. D. Creamer, S. D. Dreher, P. J. Walsh, J. Am. Chem. Soc. 2012, 134, 13765
49. A. Bellomo, J. Zhang, N. Trongsiriwat, P. J. Walsh, Chem. Sci. 2013, 4, 849.
50. B. L. H. Taylor, M. R. Harris, E. R. Jarvo, Angew. Chem. 2012, 124, 7910
51. Angew. Chem. Int. Ed. 2012, 51, 7790
52. M. R. Harris, L. E. Hanna, M. A. Greene, C. E. Moore, E. R. Jarvo, J. Am. Chem. Soc. 2013, 135, 3303
53. Q. Zhou, H. D. Srinivas, S. Dasgupta, M. P. Watson, J. Am. Chem. Soc. 2013, 135, 3307.
54. W. S. Matthews, J. E. Bares, J. E. Bartmess, F. G. Bordwell, F. J. Cornforth, G. E. Drucker, Z. Margolin, R. J. McCallum, G. J. McCollum, N. R. Vanier, J. Am. Chem. Soc. 1975, 97, 7006
55. F. G. Bordwell, Acc. Chem. Res. 1988, 21, 456.
56. M. Julia, A. Righini-Tapif, J.-N. Verpeaux, Tetrahedron 1983, 39, 3283
57. A. N. Kasatkin, A. N. Kulak, G. A. Tolstikov, S. I. Lomakina, Izv. Akad. Nauk SSSR Ser. Khim. 1988, 2159
58. J. Clayden, M. Julia, J. Chem. Soc. Chem. Commun. 1994, 1905
59. D. Seomoon, K. Lee, H. Kim, P. H. Lee, Chem. Eur. J. 2007, 13, 5197
60. J.-C. Wu, L.-B. Gong, Y. Xia, R.-J. Song, Y.-X. Xie, J.-H. Li, Angew. Chem. 2012, 124, 10047
61. Angew. Chem. Int. Ed. 2012, 51, 9909.
62. J. Tsuji, Palladium Reagents and Catalysts, Wiley, Chichester, 2004
63. F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082
64. J. M. Fox, X. Huang, A. Chieffi, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 1360
65. D. A. Culkin, J. F. Hartwig, Acc. Chem. Res. 2003, 36, 234
66. J. B. Grimm, M. H. Katcher, D. J. Witter, A. B. Northrup, J. Org. Chem. 2007, 72, 8135
67. G. Zhou, P. C. Ting, R. G. Aslanian, Tetrahedron Lett. 2010, 51, 939.
68. B. Zheng, T. Jia, P. J. Walsh, Org. Lett. 2013, 15, 1690.
69. 4 was added to a reaction promoted by LiOtBu. The special reactivity of LiOtBu in comparison to other salts, including KOtBu, is documented for C-H arylations; see:, T. Yamamoto, K. Muto, M. Komiyama, J. Canivet, J. Yamaguchi, K. Itami, Chem. Eur. J. 2011, 17, 10113. This observation may arise from different levels of ion separation in the potassium and lithium enolates. For a discussion of counterion effects on transmetallation, see
70. C. Amatore, A. Jutand, G. Le Duc, Chem. Eur. J. 2012, 18, 6616-6625.
71. H. Yorimitsu, K. Oshima, Tetrahedron 2009, 65, 1971.
72. M. G. Organ, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev, C. J. O'Brien, C. Valente, Chem. Eur. J. 2006, 12, 4749
73. C. J. Valente, M. E. Belowich, N. Hadei, M. G. Organ, Eur. J. Org. Chem. 2010, 4343.
74. Shagufta, A. K. Srivastava, R. Sharma, R. Mishra, A. K. Balapure, P. S. R. Murthy, G. Panda, Bioorg. Med. Chem. 2006, 14, 1497.