Regioselective synthesis of naphthalenes from modified Baylis-Hillman adducts via a Pd-catalyzed cyclization: 5-exo-carbopalladation, C(sp 3)-H activation to cyclopropane, ring-opening, and aromatization cascade

Tetrahedron Letters

Volumn 51, Issue 32, 2010, Pages 4267-4271

  Kim, Se Hee ^a   Lee, Hyun Seung ^a   Kim, Ko Hoon ^a   Kim, Jae Nyoung ^a  

^a Chonnam National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMOPHENYL ACETONITRILE; ACETONITRILE DERIVATIVE; CYCLOPROPANE; NAPHTHALENE; PALLADIUM; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; BAYLIS HILLMAN REACTION; CATALYSIS; CYCLIZATION; RING OPENING; SYNTHESIS;

EID: 77955313628     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.06.046     Document Type: Article

References (63)

1. For the general review on Baylis-Hillman reaction, see: D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 891
2. V. Singh, and S. Batra Tetrahedron 64 2008 4511 4574
3. J.N. Kim, and K.Y. Lee Curr. Org. Chem. 6 2002 627 645
4. K.Y. Lee, S. Gowrisankar, and J.N. Kim Bull. Korean Chem. Soc. 26 2005 1481 1490
5. P. Langer Angew. Chem., Int. Ed. 39 2000 3049 3052
6. P. Radha Krishna, R. Sachwani, and P.S. Reddy Synlett 2008 2897 2912
7. V. Declerck, J. Martinez, and F. Lamaty Chem. Rev. 109 2009 1 48
8. S. Gowrisankar, H.S. Lee, S.H. Kim, K.Y. Lee, and J.N. Kim Tetrahedron 65 2009 8769 8780
9. For the recent Pd-catalyzed reactions of modified Baylis-Hillman adducts, see: A. Vasudevan, P.-S. Tseng, and S.W. Djuric Tetrahedron Lett. 47 2006 8591 8593
10. F. Coelho, D. Veronese, C.H. Pavam, V.I. de Paula, and R. Buffon Tetrahedron 62 2006 4563 4572
11. L.K. Kohn, C.H. Pavam, D. Veronese, F. Coelho, J.E. De Carvalho, and W.P. Almeida Eur. J. Med. Chem. 41 2006 738 744
12. H. Liu, J. Yu, L. Wang, and X. Tong Tetrahedron Lett. 49 2008 6924 6928
13. M. Szlosek-Pinaud, P. Diaz, J. Martinez, and F. Lamaty Tetrahedron 63 2007 3340 3349
14. B.G. Jellerichs, J.-R. Kong, and M.J. Krische J. Am. Chem. Soc. 125 2003 7758 7759 further references were compiled in Ref. 1h
15. For our contributions on Pd-catalyzed reactions of modified Baylis-Hillman adducts, see: K.H. Kim, H.S. Lee, S.H. Kim, S.H. Kim, and J.N. Kim Chem. Eur. J. 16 2010 2375 2380
16. J.M. Kim, S.H. Kim, H.S. Lee, and J.N. Kim Tetrahedron Lett. 50 2009 1734 1737
17. K.H. Kim, E.S. Kim, and J.N. Kim Tetrahedron Lett. 50 2009 5322 5325
18. H.S. Lee, S.H. Kim, T.H. Kim, and J.N. Kim Tetrahedron Lett. 49 2008 1773 1776
19. S. Gowrisankar, H.S. Lee, J.M. Kim, and J.N. Kim Tetrahedron Lett. 49 2008 1670 1673
20. S. Gowrisankar, H.S. Lee, K.Y. Lee, J.-E. Lee, and J.N. Kim Tetrahedron Lett. 48 2007 8619 8622
21. J.M. Kim, K.H. Kim, T.H. Kim, and J.N. Kim Tetrahedron Lett. 49 2008 3248 3251
22. H.S. Lee, S.H. Kim, S. Gowrisankar, and J.N. Kim Tetrahedron 64 2008 7183 7190
23. S. Gowrisankar, K.H. Kim, S.H. Kim, and J.N. Kim Tetrahedron Lett. 49 2008 6241 6244
24. For the similar examples on δ-carbon elimination, see: H.S. Kim, S. Gowrisankar, S.H. Kim, and J.N. Kim Tetrahedron Lett. 49 2008 3858 3861
25. H.S. Kim, H.S. Lee, S.H. Kim, and J.N. Kim Tetrahedron Lett. 50 2009 3154 3157
26. H.S. Kim, S. Gowrisankar, E.S. Kim, and J.N. Kim Tetrahedron Lett. 49 2008 6569 6572 and further references were cited therein
27. 3)-H bond activation, see: F. Liron, and P. Knochel Tetrahedron Lett. 48 2007 4943 4946
28. H. Ren, Z. Li, and P. Knochel Chem. Asian J. 2 2007 416 433
29. H. Ren, and P. Knochel Angew. Chem., Int. Ed. 45 2006 3462 3465
30. G. Dyker Angew. Chem., Int. Ed. 33 1994 103 105
31. G. Dyker J. Org. Chem. 58 1993 6426 6428
32. G. Dyker Angew. Chem., Int. Ed. 31 1992 1023 1025
33. J. Hitce, P. Retailleau, and O. Baudoin Chem. Eur. J. 13 2007 792 799
34. O. Baudoin, A. Herrbach, and F. Gueritte Angew. Chem., Int. Ed. 42 2003 5736 5740
35. For some leading references to naphthalene synthesis, see: N. Asao, K. Takahashi, S. Lee, T. Kasahara, and Y. Yamamoto J. Am. Chem. Soc. 124 2002 12650 12651
36. N. Asao, T. Nogami, S. Lee, and Y. Yamamoto J. Am. Chem. Soc. 125 2003 10921 10925
37. J. Barluenga, H. Vazquez-Villa, A. Ballesteros, and J.M. Gonzalez Org. Lett. 5 2003 4121 4123
38. J. Barluenga, H. Vazquez-Villa, I. Merino, A. Ballesteros, and J.M. Gonzalez Chem. Eur. J. 12 2006 5790 5805
39. N.T. Patil, A. Konala, V. Singh, and V.V.N. Reddy Eur. J. Org. Chem. 2009 5178 5184
40. M. Shi, and J.-M. Lu J. Org. Chem. 71 2006 1920 1923
41. X. Jiang, W. Kong, J. Chen, and S. Ma Org. Biomol. Chem. 6 2008 3606 3610
42. A.S. Dudnik, T. Schwier, and V. Gevorgyan Tetrahedron 65 2009 1859 1870
43. R. Balamurugan, and V. Gudla Org. Lett. 11 2009 3116 3119
44. For our recent synthesis of naphthalene derivatives, see: S.H. Kim, Y.M. Kim, H.S. Lee, and J.N. Kim Tetrahedron Lett. 51 2010 1592 1595
45. K.Y. Lee, S.C. Kim, and J.N. Kim Tetrahedron Lett. 47 2006 977 980
46. S. Gowrisankar, K.H. Kim, and J.N. Kim Bull. Korean Chem. Soc. 29 2008 2537 2539
47. Y.J. Im, K.Y. Lee, T.H. Kim, and J.N. Kim Tetrahedron Lett. 43 2002 4675 4678
48. S. Gowrisankar, H.S. Lee, and J.N. Kim Tetrahedron Lett. 48 2007 3105 3108
49. For the synthesis of cinnamyl bromide derivatives in a stereoselective manner from Baylis-Hillman 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. -1
58. For the reductive Heck type quenching caused by DMF, see: A.M. Zawisza, and J. Muzart Tetrahedron Lett. 48 2007 6738 6742
59. J. Li, R. Hua, and T. Liu J. Org. Chem. 75 2010 2966 2970
60. J.-Y. Legros, G. Primault, M. Toffano, M.-A. Riviere, and J.-C. Fiaud Org. Lett. 2 2000 433 436
61. M. Brenda, A. Knebelkamp, A. Greiner, and W. Heitz Synlett 1991 809 810
62. For the similar oxidative decyanation of secondary nitriles to ketones, see: S.S. Kulp, and M.J. McGee J. Org. Chem. 48 1983 4097 4098
63. R.W. Freerksen, S.J. Selikson, and R.R. Wroble J. Org. Chem. 48 1983 4087 4096