Synthesis of alkyloxy stilbenes by one-pot O-alkylation-Wittig and O-alkylation-Wittig-Heck reaction sequence

Tetrahedron Letters

Volumn 54, Issue 1, 2013, Pages 80-84

  Patel, Krupa N ^a   Kamath, Bola V ^a   Bedekar, Ashutosh V ^a  

^a M S UNIVERSITY OF BARODA   (India)

Author keywords

Coupling reactions; Homogeneous catalysis; Mizoroki Heck reaction; O Alkylation; One pot reactions; Wittig reaction

Indexed keywords

BENZALDEHYDE DERIVATIVE; BENZENE; STILBENE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; HECK REACTION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; WITTIG REACTION;

TETRA;

EID: 84870290551     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.10.102     Document Type: Article

References (55)

1. For some recent reviews, see: K.M. Coakley, and M.D. McGehee Chem. Mater. 16 2004 4533
2. B. Liu, and G.C. Bazan Chem. Mater. 16 2004 4467
3. A.P.H.J. Schenning, and E.W. Meijer Chem. Commun. 2005 3245
4. Y.-J. Cheng, S.-H. Yang, and C.-S. Hsu Chem. Rev. 109 2009 5868
5. J.H. Jeong, H. Mok, Y.-K. Oh, and G. Park Bioconjugate Chem. 20 2009 5
6. W. Wu, Y. Liu, and D. Zhu Chem. Soc. Rev. 39 2010 1489
7. A. Facchetti Chem. Mater. 23 2011 733
8. J. Shin, N.S. Kang, K.H. Kim, T.W. Lee, J. Jin, M. Kim, K. Lee, B.K. Ju, J.-M. Hong, and D.H. Choi Chem. Commun. 48 2012 8490
9. M.E.A. Fegley, S.S. Pinnock, C.N. Malele, and W.E. Jones Inorg. Chim. Acta 381 2012 78
10. J. Casado, R.P. Ortiz, and J.T. Lopez Navarrete Chem. Soc. Rev. 41 2012 5672
11. H. Zhou, L. Yang, and W. You Macromolecules 45 2012 607
12. C. Wang, H. Dong, W. Hu, Y. Liu, and D. Zhu Chem. Rev. 112 2012 2208
13. A. Rajca, P.J. Boratyński, A. Olankitwanit, S. Shiraishi, M. Pink, and S. Rajca J. Org. Chem. 77 2012 2107
14. (n) L. Gera, C. Roy, M.-T. Bawolak, X. Bawolak, and F. Marceau Peptides 34 2012 433
15. Some representative examples of applications of alkyloxy conjugated molecules M.R. Pinto, B. Hu, F.E. Karasz, and L. Akcelrud Polymer 41 2000 2603
16. C. Wang, A.S. Batsanov, and M.R. Bryce J. Org. Chem. 71 2006 108
17. C. Coya, A. de Andrés, C. Zaldo, A.L. Álvarez, B. Arredondo, R. Gómez, J.L. Segura, and C. Seoane J. Appl. Phys. 105 2009 044510
18. A. Ajayaghosh, and V.K. Praveen Acc. Chem. Res. 40 2007 644
19. S.E. Denmark, and A. Thorarensen Chem. Rev. 96 1996 137
20. L.F. Tietze Chem. Rev. 96 1996 115
21. T.J.J. Muller Metal Catalyzed Cascade Reactions Vol. 19 2006 Springer-Verlag Berlin
22. D.J. Ramon, and M. Yus Angew. Chem., Int. Ed. 44 2005 1602
23. J.O. Wasilke, S.J. Obrey, R.T. Baker, and G.C. Bazan Chem. Rev. 105 2005 1001
24. A. Dömling Chem. Rev. 106 2006 17
25. K.C. Nicolaou Chem. Soc. Rev. 38 2009 2993
26. K.C. Nicolaou, D.J. Edmonds, and P.G. Bulger Angew. Chem., Int. Ed. 45 2006 7134
27. L.F. Tietze, G. Brasche, and K. Gericke In Domino Reactions in Organic Synthesis 2006 Wiley-VCH Weinheim
28. M.J. Climent, A. Corma, and S. Iborra Chem. Rev. 111 2011 1072
29. A.S. Saiyed, and A.V. Bedekar Tetrahedron Lett. 51 2010 6227
30. A.R. Chaudhary, and A.V. Bedekar Appl. Organomet. Chem. 26 2012 430
31. A.S. Saiyed, K.N. Patel, B.V. Kamath, and A.V. Bedekar Tetrahedron Lett. 53 2012 4692
32. O.I. Kolodiazhnyi Phosphorous Ylides - Chemistry and Applications in Organic Synthesis 1999 Wiley-VCH Weinheim
33. T. Mizoroki, K. Mori, and A. Ozaki Bull. Chem. Soc. Jpn. 44 1971 581-581
34. R.F. Heck, and J.P. Nolly J. Org. Chem. 37 1972 2320 2322
35. A. de Meijere, and F.E. Meyer Angew. Chem., Int. Ed. Engl. 33 1994 2379
36. I.P. Beletskaya, and A.V. Cheprakov Chem. Rev. 100 2000 3009
37. A. Jutand M. Oestreich, The Mizoroki-Heck reaction 2009 John Wiley & Sons Chichester, United Kingdom 1 50
38. C. Amatore, and A. Jutand Acc. Chem. Res. 33 2000 314
39. A. Salgado, E. Mann, F. Sanchez-Sancho, and B. Herradón Heterocycles 60 2003 57
40. M.V. Nandakumar, and J.G. Verkade Tetrahedron 61 2005 9775
41. R. Grisorio, P. Mastrorilli, C.F. Nobile, G. Romanazzi, and G.P. Suranna Tetrahedron Lett. 46 2005 2555
42. S.T. Handy Synlett 2006 3176
43. X. Zhang, A. Liu, and W. Chen Org. Lett. 10 2008 3849
44. S. Tu, L.-H. Xu, and C.-R. Yu Synth. Commun. 38 2008 2662
45. C. Burmester, S. Mataka, and T. Thiemann Synth. Commun. 40 2010 3196
46. S. Pfeiffer, and H.-H. Hörhold Macromol. Chem. Phys. 1999 1870 200
47. C.-L. Li, S.-J. Shieh, S.-C. Lin, and R.-S. Liu Org. Lett. 5 2003 1131 1134
48. Y. Yan, X. Tao, G. Xu, H. Zhao, Y. Sun, C. Wang, J. Yang, X. Yu, X. Zhao, and M. Jiang Aust. J. Chem. 58 2005 29
49. M. Shimizu, and T. Hiyama Chem. Asian J. 5 2010 1516 1531
50. R. Thomas, S. Varghese, and G.U. Kulkarni J. Mater. Chem. 19 2009 4401 4406
51. C.-H. Lin, C.-M. Tsai, G.-H. Huang, and Y.-T. Tao Macromolecules 39 2006 557 568
52. H.-C. Lin, C.-M. Tsai, and Y.-T. Tao J. Polym. Sci., Part A: Polym. Chem. 44 2006 2922
53. M. Goel, and M. Jayakannan J. Phys. Chem. B 114 2010 12508
54. J. He, B. Xu, F. Chen, H. Xia, K. Li, L. Ye, and W. Tian J. Phys. Chem. C 113 2009 9892
55. C. Coya, A. de Andrés, R. Gómez, C. Seoane, and J.L. Segura J. Lumin. 128 2008 761