Copper-mediated oxidative cross-coupling reaction of terminal alkynes with α-silyldifluoromethylphosphonates: An efficient method for α,α-difluoropropargylphosphonates

Organic Letters

Volumn 14, Issue 11, 2012, Pages 2870-2873

  Jiang, Xueliang ^a   Chu, Lingling ^a   Qing, Feng Ling ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b DONGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84861831951     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol301113v     Document Type: Article

References (56)

1. Engel, R. Chem. Rev. 1977, 77, 349
2. Romanenko, V. D.; Kukhar, V. P. Chem. Rev. 2006, 106, 3868
3. Kirsch, P. Modern Fluoroorganic Chemistry; Wiley-VCH: Weinheim, 2004.
4. Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford, U.K., 2006.
5. Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology; Wiley-Blackwell: Chichester, U.K., 2009.
6. Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881
7. Hird, M. Chem. Soc. Rev. 2007, 36, 2070
8. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305
9. O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308
10. Ritter, S. K. Chem. Eng. News 2012, 90, 10
11. Halazy, S.; Ehrhard, A.; Danzin, C. J. Am. Chem. Soc. 1991, 113, 315
12. Hebel, D.; Kirk, K. L.; Kinjo, J.; Kovács, T.; Lesiak, K.; Balzarini, J.; De Clercq, E.; Torrence, P. F. Bioorg. Med. Chem. Lett. 1991, 1, 357
13. Ye, B.; Burke, T. R., Jr. Tetrahedron 1996, 52, 9963
14. Gautier-Lefebvre, I.; Behr, J.-B.; Guillerm, G.; Ryder, N. S. Bioorg. Med. Chem. Lett. 2000, 10, 1483
15. Cox, R. J.; Hadfield, A. T.; Mayo-Martin, M. B. Chem. Commun. 2001, 1710
16. Yokomatsu, T.; Murano, T.; Akiyama, T.; Koizumi, J.; Shibuya, S.; Tsuji, Y.; Soeda, S.; Shimeno, H. Bioorg. Med. Chem. Lett. 2003, 13, 229
17. Cushman, M.; Sambaiah, T.; Jin, G.; Illarionov, B.; Fischer, M.; Bacher, A. J. Org. Chem. 2004, 69, 601
18. Mandal, P. K.; Liao, W. S. L.; McMurray, J. S. Org. Lett. 2009, 11, 3394
19. Differding, E.; Duthaler, R. O.; Krieger, A.; Rüegg, G. M.; Schmit, C. Synlett 1991, 395
20. Taylor, S. D.; Kotoris, C. C.; Dinaut, A. N.; Chen, M.-J. Tetrahedron 1998, 54, 1691
21. Hum, G.; Lee, J.; Taylor, S. D. Bioorg. Med. Chem. Lett. 2002, 12, 3471
22. Ladame, S.; Willson, M.; Périé, J. Eur. J. Org. Chem. 2002, 2640
23. Smyth, M. S.; Burke, T. R., Jr. Tetrahedron Lett. 1994, 35, 551
24. Solas, D.; Hale, R. L.; Patel, D. V. J. Org. Chem. 1996, 61, 1537
25. Benayoud, F.; Hammond, G. B. Chem. Commun. 1996, 1447
26. Wang, Z.; Gu, Y.; Zapata, A. J.; Hammond, G. B. J. Fluorine Chem. 2001, 107, 127
27. Yang, Z. Y.; Burton, D. J. J. Org. Chem. 1992, 57, 4676
28. Li, A.-R.; Chen, Q.-Y. Synthesis 1996, 606
29. Lequeux, T.; Lebouc, F.; Lopin, C.; Yang, H.; Gouhier, G.; Piettre, S. R. Org. Lett. 2000, 3, 185
30. Ozouf, P.; Binot, G.; Pommelet, J.-C.; Lequeux, T. P. Org. Lett. 2004, 6, 3747
31. Sène, A.; Diab, S.; Hienzsch, A.; Cahard, D.; Lequeux, T. Synlett 2009, 981
32. Berkowitz, D. B.; Eggen, M.; Shen, Q.; Sloss, D. G. J. Org. Chem. 1993, 58, 6174
33. Vinod, T. K.; Hayes Griffith, O.; Keana, J. F. W. Tetrahedron Lett. 1994, 35, 7193
34. Berkowitz, D. B.; Sloss, D. G. J. Org. Chem. 1995, 60, 7047
35. Matulic-Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563
36. Berkowitz, D. B.; Bhuniya, D.; Peris, G. Tetrahedron Lett. 1999, 40, 1869
37. Berkowitz, D. B.; Eggen, M.; Shen, Q.; Shoemaker, R. K. J. Org. Chem. 1996, 61, 4666
38. Piettre, S. R.; Girol, C.; Schelcher, C. G. Tetrahedron Lett. 1996, 37, 4711
39. Blades, K.; Lapôtre, D.; Percy, J. M. Tetrahedron Lett. 1997, 38, 5895
40. Blades, K.; Percy, J. M. Tetrahedron Lett. 1998, 39, 9085
41. Weiming, Q.; Burton, D. J. Tetrahedron Lett. 1996, 37, 2745
42. Yokomatsu, T.; Suemune, K.; Murano, T.; Shibuya, S. J. Org. Chem. 1996, 61, 7207
43. Yokomatsu, T.; Murano, T.; Suemune, K.; Shibuya, S. Tetrahedron 1997, 53, 815
44. Zhang, X.; Burton, D. J. Tetrahedron Lett. 2000, 41, 7791
45. Zhang, X.; Burton, D. J. J. Fluorine Chem. 2002, 116, 15
46. Feng, Z.; Chen, F.; Zhang, X. Org. Lett. 2012, 14, 1938
47. Chu, L. L.; Qing, F. L. J. Am. Chem. Soc. 2010, 132, 7262
48. Chu, L. L.; Qing, F. L. Org. Lett. 2010, 12, 5060
49. Chu, L. L.; Qing, F. L. J. Am. Chem. Soc. 2012, 134, 1298
50. Jiang, X. L.; Chu, L. L.; Qing, F. L. J. Org. Chem. 2012, 77, 1251
51. Chu, L. L.; Qing, F. L. Org. Lett. 2012, 14, 2106
52. Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165
53. Martynov, B. I.; Stepanov, A. A. J. Fluorine Chem. 1997, 85, 127
54. Kolomeitsev, A. A.; Kadyrov, A. A.; Szczepkowska-Sztolcman, J.; Milewska, M.; Koroniak, H.; Bissky, G.; Barten, J. A.; Röschenthaler, G.-V. Tetrahedron Lett. 2003, 44, 8273
55. Alexandrova, A. V.; Beier, P. J. Fluorine Chem. 2009, 130, 493
56. Kosobokov, M. D.; Dilman, A. D.; Struchkova, M. I.; Belyakov, P. A.; Hu, J. J. Org. Chem. 2012, 77, 2080