Copper-catalyzed carboarylation of alkynes via vinyl cations

Journal of the American Chemical Society

Volumn 135, Issue 34, 2013, Pages 12532-12535

  Walkinshaw, Andrew J ^a   Xu, Wenshu ^a   Suero, Marcos G ^a   Gaunt, Matthew J ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL COMPOUNDS; COPPER; POSITIVE IONS;

ARYLATIONS; ELECTRON-RICH; TETRASUBSTITUTED ALKENES; VINYL CATIONS;

HYDROCARBONS;

ALKYNE; CARBON; CATION; COPPER; NUCLEOPHILE; POLYCYCLIC AROMATIC HYDROCARBON; VINYL DERIVATIVE; ALKENE;

ARTICLE; ARYLATION; CHEMICAL STRUCTURE; CATALYSIS; CHEMISTRY; SYNTHESIS;

ALKENES; ALKYNES; CATALYSIS; CATIONS; COPPER; MOLECULAR STRUCTURE; VINYL COMPOUNDS;

EID: 84883263970     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja405972h     Document Type: Article

References (48)

1. Goldfinger, M. B.; Crawford, K. B.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 4578
2. Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2004, 126, 10204
3. Zhang, Y.; Hsung, R. P.; Zhang, X.; Huang, J.; Slafer, B. W.; Davis, A. Org. Lett. 2005, 7, 1047
4. Ataur Rahman, Md.; Ogawa, O.; Oyamada, J.; Kitamura, T. Synthesis 2008, 3755
5. Kitamura, T. Eur. J. Org. Chem. 2009, 1111
6. Vasil'ev, A. V. Russ. J. Org. Chem. 2009, 45, 1
7. Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633
8. Nevado, C.; Echavarren, A. M. Synthesis 2005, 167
9. Bandini, M. Chem. Soc. Rev. 2011, 40, 1358
10. Flynn, A. B.; Ogilvie, W. W. Chem. Rev. 2007, 107, 4698
11. Itami, K.; Kamei, T.; Yoshida, J.-I. J. Am. Chem. Soc. 2003, 125, 14670
12. Zhou, C.; Emrich, D. E.; Larock, R. C. Org. Lett. 2003, 5, 1579
13. Zhou, C.; Larock, R. C. J. Org. Chem. 2006, 71, 3184
14. Suárez, L. L.; Greaney, M. F. Chem. Commun. 2011, 7992
15. Nakao, Y.; Oda, S.; Hiyama, T. J. Am. Chem. Soc. 2004, 126, 13904
16. Nakao, Y.; Yada, A.; Hiyama, T. J. Am. Chem. Soc. 2010, 132, 10024
17. Hirata, Y.; Yada, A.; Morita, E.; Nakao, Y.; Hiyama, T.; Ohashi, M.; Ogoshi, S. J. Am. Chem. Soc. 2010, 132, 10070
18. Minami, Y.; Yoshiyasu, H.; Nakao, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2013, 52, 883
19. Patel, S. J.; Jamison, T. F. Angew. Chem., Int. Ed. 2003, 42, 1364
20. Jin, T.; Himuro, M.; Yamamoto, Y. J. Am. Chem. Soc. 2010, 132, 5590
21. Yamamoto, Y.; Gridnev, I. D.; Patil, N. T.; Jin, T. Chem. Commun. 2009, 5075
22. Phipps, R. J.; McMurray, L.; Ritter, S.; Duong, H. A.; Gaunt, M. J. J. Am. Chem. Soc. 2012, 134, 10773
23. Suero, M. G.; Bayle, E. D.; Collins, B. S. L.; Gaunt, M. J. J. Am. Chem. Soc. 2013, 135, 5332
24. Collins, B. S. L.; Suero, M. G.; Gaunt, M. J. Angew. Chem., Int. Ed. 2013, 52, 5799
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. Hickman, A. J.; Sanford, M. S. Nature 2012, 484, 177
28. Casitas, A.; King, A. E.; Parella, T.; Costas, M.; Stahl, S. S.; Ribas, X. Chem. Sci. 2010, 1, 326
29. Casitas, A.; Ribas, X. Chem. Sci 2013, 4, 2301
30. King, A. E.; Brunold, T. C.; Stahl, S. S. J. Am. Chem. Soc. 2009, 131, 5044
31. Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172
32. Phipps, R. J.; Gaunt, M. J. Science 2009, 323, 1593
33. Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2011, 133, 4260
34. Stang, P. J. J. Am. Chem. Soc. 1969, 91, 4600
35. Kelsey, D. R.; Bergman, R. G. J. Am. Chem. Soc. 1970, 93, 1941
36. Olah, G.; Mayr, H. J. Am. Chem. Soc. 1976, 98, 7333
37. Hanack, M. Angew. Chem., Int. Ed. 1978, 17, 333
38. Stang, P. J.; Rappoport, Z.; Hanack, M.; Subramanian, L. R. Vinyl cations; Academic Press: New York, 1979.
39. Rappoport, Z.; Stang, P. J. Dicoordinate Carbocations; Wiley: NewYork, 1997.
40. Okuyama, T. Acc. Chem. Res. 2002, 35, 12
41. In the absence of the DTBP we observe complete consumption of 1a and 2a but no formation of 3a.
42. At 70 C we observe a rapid decomposition of 2a. Equivalent yields of 3a could be achieved by portion wise addition of 2 × 1 equivalents of 2a at 70 C (c.f. Table 1, entry 11.)
43. Bielawski, M.; Olofsson, B. Chem. Commun. 2007, 2521
44. Bielawski, M.; Zhu, M.; Olofsson, B. Adv. Synth. Catal. 2007, 349, 2610
45. Ochiai, M.; Toyonari, M.; Nagaoka, T.; Chen, D.-W.; Kida, M. Tetrahedron Lett. 1997, 38, 6709
46. Itami, K. Pure Appl. Chem. 2012, 84, 907
47. Lednicer, D.; Lyster, S. C.; Duncan, G. W. J. Med. Chem. 1967, 10, 78
48. Kyle Hadden, M.; Galam, L.; Gestwicki, J. E.; Matts, R. L.; Blagg, B. S. J. J. Nat. Prod. 2007, 70, 2014