Copper-catalyzed electrophilic carbofunctionalization of alkynes to highly functionalized tetrasubstituted alkenes

Journal of the American Chemical Society

Volumn 135, Issue 14, 2013, Pages 5332-5335

  Suero, Marcos G ^a   Bayle, Elliott D ^a   Collins, Beatrice S L ^a   Gaunt, Matthew J ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL; CARBOMETALATION; COPPER CATALYST; CROSS COUPLING REACTIONS; FUNCTIONALIZED; TETRASUBSTITUTED ALKENES; TRIFLATES;

CHEMISTRY; SYNTHESIS (CHEMICAL);

HYDROCARBONS;

ALKENE DERIVATIVE; ALKYNE; COPPER; VINYL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ELECTROPHILICITY; FLUORINE NUCLEAR MAGNETIC RESONANCE; OXIDATION; SUBSTITUTION REACTION; SYNTHESIS;

ALKENES; ALKYNES; CATALYSIS; COPPER; MOLECULAR STRUCTURE;

EID: 84876041819     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja401840j     Document Type: Article

References (53)

1. Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079
2. Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874
3. Schore, N. E. Chem. Rev. 1988, 88, 1081
4. Fürstner, A.; Davies, P. W. Chem. Commun. 2005, 18, 2307
5. Flynn, A. B.; Ogilvie, W. W. Chem. Rev. 2007, 107, 4698
6. Normant, J. F.; Alexakis, A. Synthesis 1981, 11, 841
7. Negishi, E.-I.; Wang, G.; Rao, H.; Xu, Z. J. Org. Chem. 2010, 75, 3151
8. Negishi, E.-i; Zhang, Y.; Cederbaum, F. E.; Webb, M. B. J. Org. Chem. 1986, 51, 4080
9. Hojo, M.; Murakami, Y.; Aihara, H.; Sakuragi, R.; Baba, Y.; Hosomi, A. Angew. Chem., Int. Ed. 2001, 40, 621
10. Itami, K.; Kamei, T.; Yoshida, J.-I. J. Am. Chem. Soc. 2003, 125, 14670
11. Nishikawa, T.; Yorimitsu, H.; Oshima, K. Synlett 2004, 1573
12. Alfaro, R.; Parra, A.; Alemán, J.; García Ruano, J. L.; Tortosa, M. J. Am. Chem. Soc. 2012, 134, 15165
13. Zhou, C.; Emrich, D. E.; Larock, R. C. Org. Lett. 2003, 5, 1579
14. Zhou, C.; Larock, R. C. J. Org. Chem. 2006, 71, 3184
15. Suárez, L. L.; Greaney, M. F. Chem. Commun. 2011, 7992
16. Carey, F. A; Sundberg, R. J. Advanced Organic Chemistry Part B: Reactions and Synthesis; Springer: Berlin, 2007.
17. Koser, G. F.; Rebrovic, L.; Wettach, R. H. J. Org. Chem. 1981, 46, 4324
18. Kasumov, T. M.; Pirguliyev, N. S.; Brel, V. K.; Grishin, Y. K.; Zefirov, N. S.; Stang, P. J. Tetrahedron 1997, 53, 13139
19. Nenitzescu, C. D.; Balaban, A. T. In Friedel-Crafts and related reactions; Olah, G. A., Ed.; Interscience: New York, 1964; Vol. 3, p 1033. Catalytic carbohalogenation
20. Trost, B. M.; Pinkerton, A. B. J. Am. Chem. Soc. 2002, 124, 7376
21. Thadani, A. N.; Rawal, V. H. Org. Lett. 2002, 4, 4317
22. Sun, J.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 127, 13512
23. Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052
24. Ochiai, M.; Toyonari, M.; Nagaoka, T.; Chen, D.-W.; Kida, M. Tetrahedron Lett. 1997, 38, 6709
25. Beringer, F. M.; Geering, E. J.; Kuntz, I.; Mausner, M. J. Phys. Chem. 1956, 60, 141
26. Lockhart, T. P. J. Am. Chem. Soc. 1983, 105, 1940
27. Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172
28. Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593
29. Ciana, C.-L.; Phipps, R. J.; Brandt, J. R.; Meyer, F. M.; Gaunt, M. J. Angew. Chem., Int. Ed. 2010, 50, 457
30. Duong, H. A.; Gilligan, R. E.; Cooke, M. L.; Phipps, R. J.; Gaunt, M. J. Angew. Chem., Int. Ed. 2010, 50, 463
31. Bigot, A.; Williamson, A. E.; Gaunt, M. J. J. Am. Chem. Soc. 2011, 133, 13778
32. Phipps, R. J.; McMurray, L.; Ritter, S.; Duong, H. A.; Gaunt, M. J. J. Am. Chem. Soc. 2012, 134, 10773
33. Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133, 4260
34. Harvey, J. S.; Simonovich, S. P.; Jamison, C. R.; MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133, 13782
35. Skucas, E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2012, 134, 9090
36. Zhu, S.; MacMillan, D. W. C. J. Am. Chem. Soc. 2012, 134, 10815
37. Hickman, A. J.; Sanford, M. S. Nature 2012, 484, 177
38. King, A. E.; Brunold, T. C.; Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 5044
39. Casitas, A.; King, A. E.; Parella, T.; Costas, M.; Stahl, S. S.; Ribas, X. Chem. Sci. 2010, 1, 326
40. Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14844
41. Shen, X.; Hyde, A. M.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14076
42. Newman, S. G.; Lautens, M. J. Am. Chem. Soc. 2010, 132, 11416
43. Liu, H.; Li, C.; Qiu, D.; Tong, X. J. Am. Chem. Soc. 2011, 133, 6187
44. Jia, X.; Petrone, D. A.; Lautens, M. Angew. Chem., Int. Ed. 2012, 51, 9870
45. Roy, A. H.; Harwig, J. F. J. Am. Chem. Soc. 2001, 123, 1232
46. Engle, K. M.; Mei, T.-S.; Wang, X.; Yu, J.-Q. Angew. Chem., Int. Ed. 2011, 50, 1478
47. Souto, J. A.; Becker, P.; Iglesias, A.; Muñiz, K. J. Am. Chem. Soc. 2012, 134, 15505
48. Cochran, B. M.; Michael, F. Org. Lett. 2008, 10, 5039
49. Stang, P. J. J. Am. Chem. Soc. 1969, 91, 4600
50. Kelsey, D. R.; Bergman, R. G. J. Am. Chem. Soc. 1970, 93, 1941
51. Trifluoromethylation: Janson, P. G.; Ghoneim, I.; Ilchenko, N. O.; Szabó, K. Org. Lett. 2012, 14, 2882
52. Kang, S.-K.; Yoon, S.-K.; Kim, Y.-M. Org. Lett. 2001, 3, 2697
53. Negishi, E.-I.; Huang, Z.; Wang, G.; Mohan, S.; Wang, C.; Hattori, H. Acc. Chem. Res. 2008, 41, 1474