1,3-Diyne chemistry: Synthesis and derivations

Tetrahedron Letters

Volumn 55, Issue 17, 2014, Pages 2763-2772

  Shi, Wei ^a   Lei, Aiwen ^b  

^a HUAZHONG AGRICULTURAL UNIVERSITY   (China)

^b WUHAN UNIVERSITY   (China)

Author keywords

Cadiot Chodkiewicz coupling; Diyne chemistry; FBW rearrangement; Glaser Eglinton Hay coupling; Keyword

Indexed keywords

1,3 DIYNE DERIVATIVE; ALKYNE DERIVATIVE; FURAN DERIVATIVE; HETEROCYCLIC COMPOUND; PYRROLE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

CADIOT CHODKIEWICZ REACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; DIMERIZATION; FRITSCH BUTTENBERG WIECHELL REARRANGEMENT; GLASER EGLINTON HAY COUPLING REACTION; POLYMERIZATION; REVIEW; SYNTHESIS; CATALYST; CHEMISTRY; COLUMN CHROMATOGRAPHY; CYCLOADDITION; DEGRADATION; LOW TEMPERATURE; ORGANIC CHEMISTRY; OXIDATIVE COUPLING; REACTION ANALYSIS; REACTION TIME; SOLUBILITY;

EID: 84899117859     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.03.022     Document Type: Review

References (85)

1. R. Chauvin, and C. Lepetit Theoretical Studies on Acetylenic Scaffolds, Acetylene Chemistry-Chemistry, Biology and Material Science 2005 Wiley-VCH
2. E.T. Chernick, and R.R. Tykwinski J. Phys. Org. Chem. 26 2013 742
3. R.R. Tykwinski, W. Chalifoux, S. Eisler, A. Lucotti, M. Tommasini, D. Fazzi, Z.M. Del, and G. Zerbi Pure Appl. Chem. 82 2010 891
4. W.A. Chalifoux, and R.R. Tykwinski Nat. Chem. 2 2010 967
5. A. Lucotti, M. Tommasini, D. Fazzi, Z.M. Del, W.A. Chalifoux, M.J. Ferguson, G. Zerbi, and R.R. Tykwinski J. Am. Chem. Soc. 131 2009 4239
6. C. Wang, A.S. Batsanov, K. West, and M.R. Bryce Org. Lett. 10 2008 3069
7. S. Szafert, and J.A. Gladysz Chem. Rev. 106 2006 PR1
8. S. Eisler, A.D. Slepkov, E. Elliott, T. Luu, R. McDonald, F.A. Hegmann, and R.R. Tykwinski J. Am. Chem. Soc. 127 2005 2666
9. T. Gibtner, F. Hampel, J.-P. Gisselbrecht, and A. Hirsch Chem. - Eur. J. 8 2002 408
10. R.J. Lagow, J.J. Kampa, H.-C. Wei, S.L. Battle, J.W. Genge, D.A. Laude, C.J. Harper, R. Bau, and R.C. Stevens et al. Science 267 1995 362
11. J.-N. Tisserant, R. Hany, E. Wimmer, A. Sanchez-Ferrer, J. Adamcik, G. Wicht, F. Nuesch, D. Rentsch, A. Borgschulte, R. Mezzenga, and J. Heier Macromolecules 47 2014 721
12. J. Wang, Y. Shen, S. Kessel, P. Fernandes, K. Yoshida, S. Yagai, D.G. Kurth, H. Mohwald, and T. Nakanishi Angew. Chem., Int. Ed. 48 2009 2166
13. H. Jiang, W. Zeng, Y. Li, W. Wu, L. Huang, and W. Fu J. Org. Chem. 77 2012 5179
14. S. Kramer, J.L.H. Madsen, M. Rottlander, and T. Skrydstrup Org. Lett. 12 2010 2758
15. L. Wang, X. Yu, X. Feng, and M. Bao J. Org. Chem. 78 2013 1693
16. X. Feng, B. Tong, J.-b. Shen, W. Zhao, J.-g. Zhi, J.-b. Shi, and Y.-p. Dong Guangpuxue Yu Guangpu Fenxi 29 2009 1482
17. L. Wang, X. Yu, X. Feng, and M. Bao Org. Lett. 14 2012 2418
18. K.T. Potts, S.A. Nye, and K.A. Smith J. Org. Chem. 57 1992 3895
19. J. Kagan, and S.K. Arora J. Org. Chem. 48 1983 4317
20. P. Siemsen, R.C. Livingston, and F. Diederich Angew. Chem., Int. Ed. 39 2000 2632
21. Y.S. Zal'kind, and M.A.Zh. Aizikovich Obshch. Khim. 7 1937 227
22. G. Eglinton, and A.R. Galbraith Chem. Ind. 1956 737
23. A.S. Hay J. Org. Chem. 25 1960 1275
24. A.S. Hay J. Org. Chem. 27 1962 3320
25. G. Eglinton, and A.R. Galbraith J. Chem. Soc. 1959 889
26. F. Sondheimer, Y. Amiel, and R. Wolovsky J. Am. Chem. Soc. 79 1957 4247
27. F. Diederich, P.J. Stang, and R.R. Tykwinski Acetylene Chemistry: Chemistry, Biology and Material Science 2005 Wiley-VCH
28. J.J. Li Name Reactions: A Collection of Detailed Mechanism and Synthetic Applications 4th ed. 2009 Springer-Verlag
29. H.A. Stefani, A.S. Guarezemini, and R. Cella Tetrahedron 66 2010 7871
30. A. Lei, M. Srivastava, and X. Zhang J. Org. Chem. 1969 2002 67
31. C. Chen, Z. Ai, J. Lin, X. Hong, and C. Xi Synlett 2006 2454
32. M. Shi, and H.-X. Qian Appl. Organomet. Chem. 20 2006 771
33. F. Yang, X. Cui, Y.-N. Li, J. Zhang, G.-R. Ren, and Y. Wu Tetrahedron 1963 2007 63
34. K. Kamata, S. Yamaguchi, M. Kotani, K. Yamaguchi, and N. Mizuno Angew. Chem., Int. Ed. 47 2008 2407
35. S. Adimurthy, C.C. Malakar, and U. Beifuss J. Org. Chem. 74 2009 5648
36. S.-N. Chen, W.-Y. Wu, and F.-Y. Tsai Green Chem. 11 2009 269
37. T.-H. Hsiao, T.-L. Wu, S. Chatterjee, C.-Y. Chiu, H.-M. Lee, L. Bettucci, C. Bianchini, and W. Oberhauser J. Organomet. Chem. 694 2009 4014
38. P. Kuhn, A. Alix, M. Kumarraja, B. Louis, P. Pale, and J. Sommer Eur. J. Org. Chem. 2009 423
39. F. Nador, L. Fortunato, Y. Moglie, C. Vitale, and G. Radivoy Synthesis 2009 4027
40. D. Wang, J. Li, N. Li, T. Gao, S. Hou, and B. Chen Green Chem. 12 2010 45
41. K. Yin, C. Li, J. Li, and X. Jia Green Chem. 13 2011 591
42. S. Atobe, M. Sonoda, Y. Suzuki, T. Yamamoto, H. Masuno, H. Shinohara, and A. Ogawa Res. Chem. Intermed. 39 2013 359
43. J. Liu, J.W.Y. Lam, and B.Z. Tang Chem. Rev. 109 2009 5799
44. N. Mizuno, K. Kamata, Y. Nakagawa, T. Oishi, and K. Yamaguchi Catal. Today 157 2010 359
45. Y. Nishihara, K. Ikegashira, K. Hirabayashi, J.-I. Ando, A. Mori, and T. Hiyama J. Org. Chem. 65 2000 1780
46. K. Kukukawa, M. Kariya, and Y. Shin-Ya Kinki Daigaku Sangyo Rikogakubu Kenkyu Hokoku 10 2009 1
47. C.H. Oh, and V.R. Reddy Tetrahedron Lett. 45 2004 5221
48. M.W. Paixao, M. Weber, A.L. Braga, A.J.B. de, A.M. Deobald, and H.A. Stefani Tetrahedron Lett. 49 2008 2366
49. F.V. Singh, M.F.Z.J. Amaral, and H.A. Stefani Tetrahedron Lett. 50 2009 2636
50. G. Cahiez, A. Moyeux, J. Buendia, and C. Duplais J. Am. Chem. Soc. 129 2007 13788
51. A. Pelter, K. Smith, and M. Tabata J. Chem. Soc., Chem. Commun. 1975 857
52. J.A. Sinclair, and H.C. Brown J. Org. Chem. 41 1976 1078
53. S.V. Damle, D. Seomoon, and P.H. Lee J. Org. Chem. 68 2003 7085
54. Z. Chen, H. Jiang, A. Wang, and S. Yang J. Org. Chem. 75 2010 6700
55. P. Cadiot, and W. Chodkiewicz H.G. Viehe, Chemistry of Acetylenes 1969 Marcel Dekker New York 597 647
56. T. Luu, Y. Morisaki, N. Cunningham, and R.R. Tykwinski J. Org. Chem. 72 2007 9622
57. E. Negishi, N. Okukado, S.F. Lovich, and F.T. Luo J. Org. Chem. 49 1984 2629
58. A. Dermenci, R.E. Whittaker, and G. Dong Org. Lett. 15 2013 2242
59. S.T. Li, T. Schnabel, S. Lysenko, K. Brandhorst, and M. Tamm Chem. Commun. 2013 7189
60. A.L.K.S. Shun, and R.R. Tykwinski Angew. Chem., Int. Ed. 45 2006 1034
61. J.M. Montierth, D.R. DeMario, M.J. Kurth, and N.E. Schore Tetrahedron 54 1998 11741
62. H.-F. Jiang, and A.Z. Wang Synthesis 2007 1649
63. S. Wang, L. Yu, P. Li, L. Meng, and L. Wang Synthesis 2011 1541
64. S.A. Nye, and K.T. Potts Synthesis 1988 375
65. J. Wityak, and J.B. Chan Synth. Commun. 21 1991 977
66. M. Alami, and F. Ferri Tetrahedron Lett. 37 1996 2763
67. W. Shi, Y.D. Luo, X.C. Luo, L. Chao, H. Zhang, J. Wang, and A.W. Lei J. Am. Chem. Soc. 130 2008 14713
68. Y. Weng, B. Cheng, C. He, and A. Lei Angew. Chem., Int. Ed. 51 2012 9547
69. V. Mouries, R. Waschbuesch, J. Carran, and P. Savignac Synthesis 1998 271
70. E. Jahnke, and R.R. Tykwinski Chem. Commun. 2010 3235
71. W. Yin, C. He, M. Chen, H. Zhang, and A. Lei Org. Lett. 11 2009 709
72. E.-I. Negishi, M. Qian, F. Zeng, L. Anastasia, and D. Babinski Org. Lett. 5 2003 1597
73. M. Qian, and E. Negishi Org. Process Res. Dev. 7 2003 412
74. E.-I. Negishi, M. Hata, and C. Xu Org. Lett. 2 2000 3687
75. K.E. Schulte, J. Reisch, and L. Horner Angew. Chem. 72 1960 920
76. J.P. Beny, S.N. Dhawan, J. Kagan, and S. Sundlass J. Org. Chem. 47 1982 2201
77. J. Tang, and X. Zhao RSC Adv. 2 2012 5488
78. J. Reisch, and K.E. Schulte Angew. Chem. 73 1961 241
79. A.J. Chalk Tetrahedron Lett. 13 1972 3487
80. G. Huerta, L. Fomina, L. Rumsh, and M.G. Zolotukhin Polym. Bull. 57 2006 433
81. L. Ackermann, and R. Born Tetrahedron Lett. 45 2004 9541
82. V. Lavallo, G.D. Frey, B. Donnadieu, M. Soleilhavoup, and G. Bertrand Angew. Chem., Int. Ed. 47 2008 5224
83. G. Huerta, and L. Fomina J. Mol. Struct.: THEOCHEM 761 2006 107
84. T. Matsuda, S. Kadowaki, and M. Murakami Chem. Commun. 2007 2627
85. T. Matsuda, S. Kadowaki, Y. Yamaguchi, and M. Murakami Org. Lett. 12 2010 1056