A facile synthetic route to new fluorinated building-blocks of 1-fluoroalkynes and 1-fluorodiynes

Chinese Journal of Chemistry

Volumn 30, Issue 1, 2012, Pages 47-52

  Liu, Cuibo ^a   Ma, Hai ^a   Nie, Jing ^a   Ma, Junan ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

1 fluoroacetylene; electrophilic fluorination; terminal 1,3 diyne; terminal alkyne

Indexed keywords

EID: 84862968755     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201100445     Document Type: Article

References (38)

1. Kirsch, P., Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004.
2. Thayer, A. M.,. Chem. Eng. News, 2006, 84, 15.
3. Uneyama, K., Organofluorine Chemistry, Blackwell Publishing, Oxford, 2006.
4. Prabhakaran, J.,;, Underwood, M. D.,;, Parsey, R. V.,;, Arango, V.,;, Majo, V. J.,;, Simpson, N. R.,;, Heertum, R. V.,;, Mann, J. J.,;, Kumar, J. S. D.,. Bioorg. Med. Chem., 2007, 15, 1802.
5. Stang, P. J.,;, Diederich, F., Modern Acetylene Chemistry, Wiley-VCH, Weinheim, Germany, 1995.
6. Siemsen, P.,;, Livingston, R. C.,;, Diederich, F.,. Angew. Chem., Int. Ed., 2000, 39, 2632.
7. Minto, R. E.,;, Blacklock, B. J.,. Prog. Lipid Res., 2008, 47, 233.
8. Middleton, W. J.,;, Sharkey, W. H.,. J. Am. Chem. Soc., 1959, 81, 803.
9. Viehe, H. G.,;, Merényi, R.,;, Oth, J. F. M.,;, Sender, J. R.,;, Valange, P.,. Angew. Chem., Int. Ed., 1964, 76, 955.
10. Sauvetre, R.,;, Normant, J. F.,. Tetrahedron Lett., 1982, 23, 4325.
11. Markin, S.,;, Sauvetre, R.,. Tetrahedron Lett., 1982, 23, 4329.
12. Runge, A.,;, Sander, W. W.,. Tetrahedron Lett., 1990, 31, 5453.
13. Hanamoto, T.,;, Koga, Y.,;, kawanami, T.,;, Furuno, H.,;, Inanaga, J.,. Angew. Chem., Int. Ed., 2004, 43, 3582.
14. Tajbakhsh, M.,;, Habibzadeh, S.,. Letters in Organic Chemistry, 2007, 4, 512.
15. Hein, J. E.,;, Tripp, J. C.,;, Krasnova, L. T.,;, Sharpless, B.,;, Fokin, V. V.,. Angew. Chem., Int. Ed., 2009, 48, 8018.
16. Li, L.-S.,;, Wu, Y.-L.,. Tetrahedron Lett., 2002, 43, 2427.
17. Reddy, K. R.,;, Venkateshwar, W.,;, Maheswari, C. U.,;, Kumar, P. S.,. Tetrahedron Lett., 2010, 51, 2170.
18. Luithle, J. E. A.,;, Pietruzka, J.,. Eur. J. Org. Chem., 2000, 2557.
19. Manickam, M. C. D.,;, Annalakshmi, S.,;, Pitchumani, K.,;, Srinivasan, C.,. Org. Biomol. Chem., 2005, 3, 1008.
20. Chen, Z.,;, Jiang, H.,;, Li, Y.,;, Qi, C.,. Chem. Commun., 2010, 46, 8049.
21. Abele, E.,;, Rubina, K.,;, Abele, R.,;, Gaukhman, A.,;, Lukevics, E.,. J. Chem. Res. (S), 1998, 618.
22. Martins, M. A. P.,;, Emmerich, D. J.,;, Pereira, C. M. P.,;, Cunico, W.,;, Rossato, M.,;, Zanatta, N.,;, Bonacorso, H. G.,. Tetrahedron Lett., 2004, 45, 4935.
23. Tajbakhsh, M.,;, Khazaei, A.,;, Mahalli, M. S.,;, Vaghi, R. G.,. Phosphorus, Sulfur, Silicon, 2004, 179, 1159.
24. Usanov, D.,;, Yamamoto, H.,. J. Am. Chem. Soc., 2011, 133, 1286.
25. Liu, Y.,;, Zhong, Z.,;, Nakajima, K.,;, Takahashi, T.,. J. Org. Chem., 2002, 67, 7451.
26. Yao, M.-L.,;, Reddy, M. S.,;, Yong, L.,;, Walfish, I.,;, Blevins, D. W.,;, Kabalka, G. W.,. Org. Lett., 2010, 12, 700.
27. Lal, G. S.,;, Pez, G. P.,;, Syvret, R. G.,. Chem. Rev., 1996, 96, 1737.
28. Ma, J.-A.,;, Cahard, D.,. Tetrahedron: Asymmetry, 2004, 15, 1007.
29. Ma, J.-A.,;, Cahard, D.,. J. Fluorine Chem., 2004, 125, 1357.
30. Cui, H.-F.,;, Dong, K.-Y.,;, Zhang, G.-W.,;, Wang, L.,;, Ma, J.-A.,. Chem. Commun., 2007, 22, 2284.
31. Nie, J.,;, Zhu, H.-W.,;, Cui, H.-F.,;, Hua, M.-Q.,;, Ma, J.-A.,. Org. Lett., 2007, 9, 3053.
32. Wang, L.,;, Meng, W.,;, Zhu, C.-L.,;, Zheng, Y.,;, Nie, J.,;, Ma, J.-A.,. Angew. Chem., Int. Ed., 2011, 50, 9442.
33. Briones, J. F.,;, Davies, H. M.,. Org. Lett., 2011, 13, 3984.
34. Reber, S.,;, Knöpfel, T. F.,;, Carreira, E. M.,. Tetrahedron, 2003, 59, 6813.
35. Trost, B. M.,;, Chan, V. S.,;, Yamamoto, D.,. J. Am. Chem. Soc., 2010, 132, 5186.
36. Aikawa, K.,;, Hioki, Y.,;, Mikami, K.,. Org. Lett., 2010, 12, 5716.
37. Turlington, M.,;, Du, Y.,;, Ostrum, S. G.,;, Santosh, V.,;, Wren, K.,;, Lin, T.,;, Sabat, M.,;, Pu, L.,. J. Am. Chem. Soc., 2011, 133, 11780.
38. Graham, E. R.,;, Tykwinski, R. R.,. J. Org. Chem., 2011, 76, 6574.