Palladium-catalyzed annulation of 2-substituted silylethynyloxybiaryls through δ-C-H activation

Chemistry Letters

Volumn 43, Issue 11, 2014, Pages 1791-1793

  Minami, Yasunori ^a,b   Anami, Tomohiro ^a   Hiyama, Tamejiro ^a,b  

^a CHUO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84914817294     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.140725     Document Type: Note

References (70)

1. a) Comprehensive Heterocyclic Chemistry III, ed. by A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor, Elsevier Ltd., Oxford, 2008, Vol. 3, and previous editions of this series.
2. b) B. Voigt, L. Meijer, O. Lozach, C. Schächtele, F. Totzke, A. Hilgeroth, Bioorg. Med. Chem. Lett. 2005, 15, 823.
3. H.-J. Knölker, K. R. Reddy, Chem. Rev. 2002, 102, 4303.
4. J. Chen, Y. Cao, Macromol. Rapid Commun. 2007, 28, 1714.
5. e) Y. Yamamoto, Chem. Soc. Rev. 2014, 43, 1575.
6. a) L. T. Scott, P.-C. Cheng, M. M. Hashemi, M. S. Bratcher, D. T. Meyer, H. B. Warren, J. Am. Chem. Soc. 1997, 119, 10963.
7. b) H.-J. Knölker, A. Braier, D. J. Bröcher, P. G. Jones, H. Piotrowski, Tetrahedron Lett. 1999, 40, 8075.
8. L.-C. Campeau, M. Parisien, M. Leblanc, K. Fagnou, J. Am. Chem. Soc. 2004, 126, 9186.
9. L.-C. Campeau, M. Parisien, A. Jean, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 581.
10. e) L.-C. Campeau, P. Thansandote, K. Fagnou, Org. Lett. 2005, 7, 1857.
11. f) D. S. Roman, Y. Takahashi, A. B. Charette, Org. Lett. 2011, 13, 3242.
12. g) C.-L. Sun, Y.-F. Gu, W.-P. Huang, Z.-J. Shi, Chem. Commun. 2011, 47, 9813.
13. h) E. Campos-Gómez, P. J. Campos, H. F. González, M. A. Rodríguez, Tetrahedron 2012, 68, 4292.
14. J. Zhou, L.-Z. Huang, Y.-Q. Li, Z.-T. Du, Tetrahedron Lett. 2012, 53, 7036.
15. j) J. Zhao, N. Asao, Y. Yamamoto, T. Jin, J. Am. Chem. Soc. 2014, 136, 9540.
16. a) A. Fürstner, V. Mamane, J. Org. Chem. 2002, 67, 6264.
17. b) A. Fürstner, V. Mamane, Chem. Commun. 2003, 2112.
18. V. Mamane, P. Hannen, A. Fürstner, Chem.-Eur. J. 2004, 10, 4556.
19. H.-C. Shen, J.-M. Tang, H.-K. Chang, C.-W. Yang, R.-S. Liu, J. Org. Chem. 2005, 70, 10113.
20. e) A. Fürstner, J. W. J. Kennedy, Chem.-Eur. J. 2006, 12, 7398.
21. f) K. Komeyama, R. Igawa, K. Takaki, Chem. Commun. 2010, 46, 1748.
22. g) T.-A. Chen, T.-J. Lee, M.-Y. Lin, S. M. A. Sohel, E. W.-G. Diau, S.-F. Lush, R.-S. Liu, Chem.-Eur. J. 2010, 16, 1826.
23. h) T. Matsuda, T. Moriya, T. Goya, M. Murakami, Chem. Lett. 2011, 40, 40.
24. J. Carreras, M. Patil, W. Thiel, M. Alcarazo, J. Am. Chem. Soc. 2012, 134, 16753.
25. j) M. Weimar, R. C. de Costa, F.-H. Lee, M. J. Fuchter, Org. Lett. 2013, 15, 1706.
26. k) N. Chernyak, V. Gevorgyan, J. Am. Chem. Soc. 2008, 130, 5636.
27. N. Chernyak, V. Gevorgyan, Adv. Synth. Catal. 2009, 351, 1101.
28. N. Chernyak, S. I. Gorelsky, V. Gevorgyan, Angew. Chem., Int. Ed. 2011, 50, 2342.
29. n) W. Lim, Y. H. Rhee, Eur. J. Org. Chem. 2013, 460.
30. a) K. Sawada, H. Hirai, P. Golden, S. Okada, Y. Sawada, M. Hashimoto, H. Tanaka, Chem. Pharm. Bull. 1998, 46, 1683.
31. b) L. Zhi, C. M. Tegley, B. Pio, J. P. Edwards, T. K. Jones, K. B. Marschke, D. E. Mais, B. Risek, W. T. Schrader, Bioorg. Med. Chem. Lett. 2003, 13, 2071.
32. L. Zhi, C. M. Tegley, B. Pio, J. P. Edwards, M. Motamedi, T. K. Jones, K. B. Marschke, D. E. Mais, B. Risek, W. T. Schrader, J. Med. Chem. 2003, 46, 4104.
33. B.-C. Hong, P. Kotame, C.-W. Tsai, J.-H. Liao, Org. Lett. 2010, 12, 776.
34. e) L. P. T. Hong, J. M. White, C. D. Donner, Aust. J. Chem. 2012, 65, 58.
35. f) Organic Photochromic and Thermochromic Compounds, ed. by J. C. Crano, R. J. Guglielmetti, Plenum Press, New York, 1999.
36. g) C.-G. Huang, K. A. Beverldge, P. Wan, J. Am. Chem. Soc. 1991, 113, 7676.
37. h) Y. Shi, P. Wan, Chem. Commun. 1997, 273.
38. a) J. P. Devlin, Can. J. Chem. 1975, 53, 343.
39. b) C.-G. Huang, D. Shukla, P. Wan, J. Org. Chem. 1991, 56, 5437.
40. D. L. J. Clive, S. P. Fletcher, D. Liu, J. Org. Chem. 2004, 69, 3282.
41. B. Wang, M. Li, S. Xu, H. Song, B. Wang, J. Org. Chem. 2006, 71, 8291.
42. e) C.-L. Sun, H. Li, D.-G. Yu, M. Yu, X. Zhou, X.-Y. Lu, K. Huang, S.-F. Zheng, B.-J. Li, Z.-J. Shi, Nat. Chem. 2010, 2, 1044.
43. f) S. Furuyama, H. Togo, Synlett 2010, 2325.
44. g) L. Mahendar, J. Krishna, A. G. K. Reddy, B. V. Ramulu, G. Satyanarayana, Org. Lett. 2012, 14, 628.
45. h) E. Motti, N. Della Ca', D. Xu, A. Piersimoni, E. Bedogni, Z.-M. Zhou, M. Catellani, Org. Lett. 2012, 14, 5792.
46. A. Ahmed, S. Dhara, J. K. Ray, Tetrahedron Lett. 2013, 54, 1673.
47. a) Y. Minami, Y. Shiraishi, K. Yamada, T. Hiyama, J. Am. Chem. Soc. 2012, 134, 6124.
48. b) Y. Minami, K. Yamada, T. Hiyama, Angew. Chem., Int. Ed. 2013, 52, 10611.
49. Y. Minami, M. Kanda, T. Hiyama, Chem. Lett. 2014, 43, 181.
50. Y. Minami, M. Kanda, T. Hiyama, Chem. Lett. 2014, 43, 1408.
51. a) R. Takeuchi, H. Yasue, J. Org. Chem. 1993, 58, 5386.
52. b) K. Tanaka, G. C. Fu, Org. Lett. 2002, 4, 933.
53. M. Murakami, T. Itahashi, Y. Ito, J. Am. Chem. Soc. 2002, 124, 13976.
54. K. Takeishi, K. Sugishima, K. Sasaki, K. Tanaka, Chem.-Eur. J. 2004, 10, 5681.
55. f) M. Tobisu, I. Hyodo, M. Onoe, N. Chatani, Chem. Commun. 2008, 6013.
56. h) P. Gandeepan, C.-H. Cheng, J. Am. Chem. Soc. 2012, 134, 5738.
57. T. Xu, G. Dong, Angew. Chem., Int. Ed. 2012, 51, 7567.
58. j) T. Xu, H. M. Ko, N. A. Savage, G. Dong, J. Am. Chem. Soc. 2012, 134, 20005.
59. k) P. Gandeepan, C.-H. Cheng, Org. Lett. 2013, 15, 2084.
60. E. Parker, N. Cramer, Organometallics 2014, 33, 780.
61. T. Iitsuka, K. Hirano, T. Satoh, M. Miura, Chem.-Eur. J. 2014, 20, 385.
62. M. Shindo, Tetrahedron 2007, 63, 10.
63. 2 did not proceed the reaction.
64. Homocycloadducts of 1c were generated mainly in 41% yield, suggesting that bulky silyl groups avoid the dimeric forms of 1. For the dimeric forms, see reference 6a.
65. J. L. Kiplinger, T. G. Richmond, C. E. Osterberg, Chem. Rev. 1994, 94, 373.
66. CCDC-1013075 (3) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/data-request/cif.
67. S. Ma, G. Villa, P. S. Thuy-Boun, A. Homs, J.-Q. Yu, Angew. Chem., Int. Ed. 2014, 53, 734.
68. 1. See the Supporting Information for detail.
69. 3, suggesting that 6-C-H bond cleavage of 1a is assisted by 2-phenyl group with remaining unexplored.
70. The mechanism of the cleavages of C-H bonds at C1 and C10 position is discussed in the Supporting Information.