Nickel-catalyzed cross-coupling of gem-difluoropropargyl bromide with aryl boronic acids

Acta Chimica Sinica

Volumn 73, Issue 5, 2015, Pages 383-387

  Xiao, Yulan ^a   Pan, Qiang ^a   Zhang, Xingang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Aryl boronic acids; Cross coupling reaction; Gem difluoropropargyl bromide; Nickel

Indexed keywords

EID: 84935077256     PISSN: 05677351     EISSN: None     Source Type: Journal    
DOI: 10.6023/A15010042     Document Type: Article

References (47)

1. Smart, B. E. J. Fluorine Chem. 2001, 109, 3.
2. Maienfisch, P.; Hall, R. G. Chimia 2004, 58, 93.
3. Special issue on "Fluorine in the Life Sciences", ChemBioChem 2004, 5, 557.
4. Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
5. Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
6. Wang, J.; Sanchez-Rosello, M.; Acena, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshok, V. A.; Liu, H. Chem. Rev. 2014, 114, 243.
7. Gribble, G. W. Chem. Soc. Rev. 1999, 28, 335.
8. Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.
9. O'Hagan, D.; Schaffrath, C.; Cobb, S. L.; Hamilton, J. T. G.; Murphy, C. D. Nature 2002, 416, 279.
10. Arnaud, C. H. Chem. Eng. News 2014, 92, 34.
11. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079.
12. Godoi, B.; Schumacher, R. F.; Zeni, G. Chem. Rev. 2011, 111, 2937.
13. Acetylene Chemistry: Chemistry, Biology and Material Science, Eds.: Diederich, F.; Stang, P. J.; Tykwinski, R. R., Wiley-VCH, Weinheim, 2005.
14. Blackburn, C. M.; England, D. A.; Kolkmann, F. J. Chem. Soc. Chem. Commun. 1981, 930.
15. Blackburn, G. M.; Kent, D. E.; Kolkmann, F. J. Chem. Soc., Perkin Trans. 1 1984, 1119.
16. Kitazume, T.; Kamazaki, T. Experimental Methods in Organic Fluorine Chemistry, Gordon and Breach Science, Tokyo, 1998.
17. Yang, Y.; You, Z.; Qing, F.-L. Acta Chim. Sinica 2012, 70, 2323.
18. Qiu, X.-L.; Xu, X.-H.; Qing, F.-L. Tetrahedron 2010, 66, 789.
19. Meanwell, N. A. J. Med. Chem. 2011, 54, 2529.
20. Bannwarth, P.; Gree, D.; Gree, R. Tetrahedron Lett. 2010, 51, 2413.
21. Khalaf, A.; Gree, D.; Abdallah, H.; Jaber, N.; Hachem, A.; Gree, R. Tetrahedron 2011, 67, 3881.
22. Li, Y.; Wheeler, K. A.; Dembinski, R. Org. Biomol. Chem. 2012, 10, 2395.
23. Baskin, J. M.; Prescher, J. A.; Laughlin, S. T.; Agard, N. J.; Chang, P. V.; Miller, I. A.; Lo, A.; Codelli, J. A.; Bertozzi, C. R. Proc. Natl. Acad. Sci. USA 2007, 104, 16793.
24. Xu, B.; Mashuta, M. S.; Hammond, G. B. Angew. Chem., Int. Ed. 2006, 45, 7265.
25. Xu, B.; Hammond, G. B. Chem. Eur. J. 2008, 14, 10029.
26. Mae, M.; Hong, J. A.; Hammond, G. B.; Uneyama, K. Tetrahedron Lett. 2005, 46, 1787.
27. Surmont, R.; Verniest, G.; Kimpe, N. D. Org. Lett. 2009, 11, 2920;
28. Lin, J.; Yue, X.; Huang, P.; Cui, D.; Qing, F.-L. Synthesis 2010, 267.
29. Kwok, P. -Y.; Muellner, F. W.; Chen, C.-K.; Fried, J. J. Am. Chem. Soc. 1987, 109, 3684.
30. Liu, G.; Mori, S.; Wang, X.; Noritake, S.; Tokunaga, E.; Shibata, N. New J. Chem. 2012, 36, 1769;
31. Xu, B.; Hammond, G. B. Angew. Chem., Int. Ed. 2005, 44, 7404.
32. Feng, Z.; Min, Q.-Q.; Xiao, Y.-L.; Zhang, B.; Zhang, X. Angew. Chem., Int. Ed. 2014, 53, 1669.
33. Min, Q.-Q.; Yin, Z.; Feng, Z.; Guo, W.-H.; Zhang, X. J. Am. Chem. Soc. 2014, 136, 1230.
34. Xiao, Y.-L.; Zhang, B.; Feng, Z.; Zhang, X. Org. Lett. 2014, 16, 4822.
35. Yu, Y.-B.; He, G.-Z.; Zhang, X. Angew. Chem., Int. Ed. 2014, 53, 10457.
36. Gu, J.-W.; Guo, W.-H.; Zhang, X. Org. Chem. Front. 2015, 2, 38.
37. Fujikawa, K.; Fujioka, Y.; Kobayashi, A.; Amii, H. Org. Lett. 2011, 13, 5560.
38. Feng, Z.; Chen, F.; Zhang, X. Org. Lett. 2012, 14, 1938.
39. Feng, Z.; Xiao, Y.-L.; Zhang, X. Org. Chem. Front. 2014, 1, 113.
40. Xiao, Y.-L.; Guo, W.-H.; He, G.-Z.; Pan, Q.; Zhang, X. Angew. Chem., Int. Ed. 2014, 53, 9909.
41. Huang, X.-T.; Chen, Q.-Y. J. Org. Chem. 2001, 66, 4651.
42. Wilsily, A.; Tramutola, F.; Owston, N. A.; Fu, G. C. J. Am. Chem. Soc. 2012, 134, 5794.
43. Zultanski, S. L.; Fu, G. C. J. Am. Chem. Soc. 2013, 135, 624.
44. Jones, G. D.; Martin, J. L.; McFarland, C.; Allen, O. R.; Hall, R. E.; Haley, A. D.; Brandon, R. J.; Konovalova, T.; Desrochers, P. J.; Pulay, P.; Vicic, D. A. J. Am. Chem. Soc. 2006, 128, 13175.
45. Phapale, V. B.; Bunuel, E.; Garcia-Iglesias, M.; Cardenas, D. J. Angew. Chem., Int. Ed. 2007, 46, 8790.
46. Lin, X.; Phillips, D. L. J. Org. Chem. 2008, 73, 3680.
47. Hu, X. Chem. Sci. 2011, 2, 1867.