An efficient synthesis of o-terphenyls from Morita-Baylis-Hillman adducts of cinnamaldehydes: A consecutive bromination, Wittig reaction, 6π-electrocyclization, and an aerobic oxidation process

Tetrahedron Letters

Volumn 54, Issue 20, 2013, Pages 2476-2479

  Lim, Cheol Hee ^a   Kim, Sung Hwan ^a   Kim, Ko Hoon ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

6 Electrocyclization; Aerobic oxidation; Morita Baylis Hillman adducts; o Terphenyls

Indexed keywords

2 TERPHENYL DERIVATIVE; CINNAMALDEHYDE DERIVATIVE; PHENYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; BROMINATION; CYCLIZATION; DIELS ALDER REACTION; ELECTROCHEMISTRY; ELECTROCYCLIZATION; MORITA BAYLIS HILLMAN REACTION; ONE POT SYNTHESIS; OXIDATION; SYNTHESIS; WITTIG REACTION;

EID: 84876121569     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.02.104     Document Type: Article

References (69)

1. For the synthesis of o-terphenyls and their applications, see: H. Yoshida, K. Okada, S. Kawashima, K. Tanino, and J. Ohshita Chem. Commun. 46 2010 1763 1765
2. L. Zhai, R. Shukla, S.H. Wadumethrige, and R. Rathore J. Org. Chem. 75 2010 4748 4760
3. L. Zhai, R. Shukla, and R. Rathore Org. Lett. 11 2009 3474 3477
4. M.J. Rahman, J. Yamakawa, A. Matsumoto, H. Enozawa, T. Nishinaga, K. Kamada, and M. Iyoda J. Org. Chem. 73 2008 5542 5548
5. S. Vagin, and M. Hanack Eur. J. Org. Chem. 2003 2661 2669
6. K. Ogura, M. Takeda, J.R. Xie, M. Akazome, and S. Matsumoto Tetrahedron Lett. 42 2001 1923 1925
7. J.P. Gao, X.S. Meng, T.P. Bender, S. MacKinnon, V. Grand, and Z.Y. Wang Chem. Commun. 1999 1281 1282
8. E. Brenna, C. Fuganti, and S. Serra J. Chem. Soc., Perkin Trans. 1 1998 901 904
9. Y.-I. Matsushita, K. Sakamoto, T. Murakami, and T. Matsui Synth. Commun. 24 1994 3307 3313
10. G. Hanson, and D.S. Kemp J. Org. Chem. 46 1981 5441 5443
11. C.H. Lim, S.H. Kim, K.H. Park, J. Lee, and J.N. Kim Tetrahedron Lett. 54 2013 387 391
12. For the synthesis of poly-substituted benzenes from MBH adducts, see: E.S. Kim, K.H. Kim, S.H. Kim, and J.N. Kim Tetrahedron Lett. 50 2009 5098 5101
13. S.C. Kim, K.Y. Lee, H.S. Lee, and J.N. Kim Tetrahedron 64 2008 103 109 and further references cited therein
14. S.J. Kim, S.H. Kim, K.H. Kim, and J.N. Kim Bull. Korean Chem. Soc. 29 2008 876 878
15. D.Y. Park, K.Y. Lee, and J.N. Kim Tetrahedron Lett. 48 2007 1633 1636
16. D.Y. Park, S. Gowrisankar, and J.N. Kim Tetrahedron Lett. 47 2006 6641 6645
17. D.Y. Park, S.J. Kim, T.H. Kim, and J.N. Kim Tetrahedron Lett. 47 2006 6315 6319
18. S.C. Kim, H.S. Lee, Y.J. Lee, and J.N. Kim Tetrahedron Lett. 47 2006 5681 5685
19. M.J. Lee, K.Y. Lee, D.Y. Park, and J.N. Kim Tetrahedron 62 2006 3128 3136
20. M.J. Lee, K.Y. Lee, S. Gowrisankar, and J.N. Kim Tetrahedron Lett. 47 2006 1355 1358
21. P.-Y. Chen, H.-M. Chen, L.-Y. Chen, J.-Y. Tzeng, J.-C. Tsai, P.-C. Chi, S.-R. Li, and E.-C. Wang Tetrahedron 63 2007 2824 2828
22. For some selected examples on 6π-electrocyclizations to form dihydrobenzene derivatives, see: R. Hayashi, M.C. Walton, R.P. Hsung, J.H. Schwab, and X. Yu Org. Lett. 12 2010 5768 5771
23. L.M. Bishop, R.E. Roberson, R.G. Bergman, and D. Trauner Synthesis 2010 2233 2244
24. D. Leboeuf, L. Iannazzo, A. Geny, M. Malacria, K.P.C. Vollhardt, C. Aubert, and V. Gandon Chem. Eur. J. 16 2010 8904 8913
25. L.M. Bishop, J.E. Barbarow, R.G. Bergman, and D. Trauner Angew. Chem., Int. Ed. 47 2008 8100 8103
26. C.L. Benson, and F.G. West Org. Lett. 9 2007 2545 2548
27. H.W. Sunnemann, M.G. Banwell, and A. de Meijere Eur. J. Org. Chem. 2007 3879 3893
28. S. Brandange, and H. Leijonmarck Chem. Commun. 2004 292 293
29. E.N. Marvell, C. Hilton, and M. Cleary J. Org. Chem. 48 1983 4272 4275
30. For the tandem 6π-electrocyclization and oxidative aromatization process, see: B.E. Moulton, H. Dong, C.T. O'Brien, S.B. Duckett, Z. Lin, and I.J.S. Fairlamb Org. Biomol. Chem. 6 2008 4523 4532
31. R. von Essen, D. Frank, H.W. Sunnemann, D. Vidovic, J. Magull, and A. de Meijere Chem. Eur. J. 11 2005 6583 6592
32. R.W. Rickards, and D. Skropeta Tetrahedron 58 2002 3793 3800
33. C. Dell'Erba, A. Gabellini, A. Mugnoli, M. Novi, G. Petrillo, and C. Tavani Tetrahedron 57 2001 9025 9031
34. K. Voigt, P. von Zezschwitz, K. Rosauer, A. Lansky, A. Adams, O. Reiser, and A. de Meijere Eur. J. Org. Chem. 1998 1521 1534
35. L. Bianchi, C. Dell'Erba, M. Maccagno, A. Mugnoli, M. Novi, G. Petrillo, F. Sancassan, and C. Tavani J. Org. Chem. 68 2003 5254 5260
36. L. Bianchi, C. Dell'Erba, M. Maccagno, G. Petrillo, E. Rizzato, F. Sancassan, E. Severi, and C. Tavani J. Org. Chem. 70 2005 8734 8738
37. J.W. Lim, K.H. Kim, S.H. Kim, and J.N. Kim Tetrahedron Lett. 53 2012 5449 5454
38. P. Xie, Y. Huang, and R. Chen Chem. Eur. J. 18 2012 7362 7366 and this paper described a phosphine-mediated benzannulation reaction between β,γ-unsaturated α-ketoester and MBH carbonate
39. For the general reviews on MBH reaction, see: D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 891
40. D. Basavaiah, B.S. Reddy, and S.S. Badsara Chem. Rev. 110 2010 5447 5674
41. V. Singh, and S. Batra Tetrahedron 64 2008 4511 4574
42. V. Declerck, J. Martinez, and F. Lamaty Chem. Rev. 109 2009 1 48
43. Ciganek, E. In Organic Reactions; Paquette, L. A., Ed.; John Wiley & Sons: New York, 1997; Vol. 51, pp 201-350
44. J.N. Kim, and K.Y. Lee Curr. Org. Chem. 6 2002 627 645
45. K.Y. Lee, S. Gowrisankar, and J.N. Kim Bull. Korean Chem. Soc. 26 2005 1481 1490
46. S. Gowrisankar, H.S. Lee, S.H. Kim, K.Y. Lee, and J.N. Kim Tetrahedron 65 2009 8769 8780
47. M. Shi, F.-J. Wang, M.-X. Zhao, and Y. Wei The Chemistry of the Morita-Baylis-Hillman Reaction 2011 RSC Publishing Cambridge, UK
48. For the preparation of the MBH adducts of cinnamaldehydes, see: K.H. Kim, H.S. Lee, Y.M. Kim, and J.N. Kim Bull. Korean Chem. Soc. 32 2011 1087 1090 and further references cited therein
49. For the synthesis of MBH bromides in a stereoselective manner from MBH adducts, see: S. Gowrisankar, S.H. Kim, and J.N. Kim Bull. Korean Chem. Soc. 30 2009 726 728 and further references cited therein
50. D. Basavaiah, K.R. Reddy, and N. Kumaragurubaran Nat. Protoc. 2 2007 2665 2676
51. B. Das, J. Banerjee, and N. Ravindranath Tetrahedron 60 2004 8357 8361
52. L. Fernandes, A.J. Bortoluzzi, and M.M. Sa Tetrahedron 60 2004 9983 9989
53. M.M. Sa, M.D. Ramos, and L. Fernandes Tetrahedron 62 2006 11652 11656
54. J. Deng, X.-P. Hu, J.-D. Huang, S.-B. Yu, D.-Y. Wang, Z.-C. Duan, and Z. Zheng J. Org. Chem. 73 2008 2015 2017
55. K.Y. Lee, Y.J. Lee, and J.N. Kim Bull. Korean Chem. Soc. 28 2007 143 146
56. K.Y. Lee, D.Y. Park, and J.N. Kim Bull. Korean Chem. Soc. 27 2006 1489 1492
57. B. Das, K. Damodar, N. Bhunia, and B. Shashikanth Tetrahedron Lett. 50 2009 2072 2074
58. K.H. Kim, S.H. Kim, S. Park, and J.N. Kim Tetrahedron 67 2011 3328 3336
59. For the Wittig type reaction of MBH adducts and their synthetic application, see: R. Zhou, C. Wang, H. Song, and Z. He Org. Lett. 12 2010 976 979
60. C.G. Lee, K.Y. Lee, S.J. Kim, and J.N. Kim Bull. Korean Chem. Soc. 28 2007 719 720
61. R.M. Crist, P.V. Reddy, and B. Borhan Tetrahedron Lett. 42 2001 619 621
62. C. Muthiah, K.S. Kumar, J.J. Vittal, and K.C.K. Swamy Synlett 2002 1787 1790
63. A. Palmelund, E.L. Myers, L.R. Tai, S. Tisserand, C.P. Butts, and V.K. Aggarwal Chem. Commun. 2007 4128 4130
64. For the synthesis of methyl 5-phenyl-2-styrylpenta-2,4-dienoate (4a), see: S.-K. Kang, Y.-T. Lee, and S.-H. Lee Tetrahedron Lett. 40 1999 3573 3576
65. 3, 75 MHz) δ 45.63, 47.24, 51.90, 122.50, 126.66, 126.71, 127.72, 127.82, 127.99, 129.07, 129.09, 130.78, 137.80, 138.28, 139.56, 166.08. The result strongly confirmed that the major isomer of 4a is an E,E,E-triene, as shown in Scheme 1
66. 4 was helpful for the increase of the yield of 4a by suppressing the hydrolysis of a phosphonium salt. For the hydrolysis of phosphonium salt, see: K.Y. Lee, J.E. Na, M.J. Lee, and J.N. Kim Tetrahedron Lett. 45 2004 5977 5981
67. B. Siegel J. Am. Chem. Soc. 101 1979 2265 2268
68. For the synthesis of methyl 2-methyl-5-phenylpenta-2,4-dienoate, see: L. Meier, M. Ferreira, and M.M. Sa Heteroat. Chem. 23 2012 179 186
69. K. Pachamuthu, and Y.D. Vankar Tetrahedron Lett. 39 1998 5439 5442