Nickel- and copper-catalyzed direct alkynylation of azoles and polyfluoroarenes with terminal alkynes under O2 or atmospheric conditions

Organic Letters

Volumn 12, Issue 10, 2010, Pages 2358-2361

  Matsuyama, Naoto ^a   Kitahara, Masanori ^a   Hirano, Koji ^a   Satoh, Tetsuya ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALKYNE; COPPER; DRUG DERIVATIVE; FLUOROBENZENE; NICKEL; OXYGEN; PYRROLE DERIVATIVE;

ARTICLE; ATMOSPHERE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETYLENE; ALKYNES; ATMOSPHERE; AZOLES; CATALYSIS; COPPER; FLUOROBENZENES; MOLECULAR STRUCTURE; NICKEL; OXYGEN; STEREOISOMERISM;

EID: 77952339522     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100699g     Document Type: Article

References (40)

1. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46
2. Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979
3. Tykwinski, R. R. Angew. Chem., Int. Ed. 2003, 42, 1566
4. Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874
5. Doucet, H.; Hierso, J.-C. Angew. Chem., Int. Ed. 2007, 46, 834
6. Plenio, H. Angew. Chem., Int. Ed. 2008, 47, 6954
7. Ga: Kobayashi, K.; Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2002, 124, 8528
8. Amemiya, R.; Fujii, A.; Yamaguchi, M. Tetrahedron Lett. 2004, 45, 4333
9. Pd: Seregin, I. V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 7742
10. Gu, Y.; Wang, X.-m. Tetrahedron Lett. 2009, 50, 763
11. Rodriguez, A.; Fennessy, R. V.; Moran, W. J. Tetrahedron Lett. 2009, 50, 3942
12. Tobisu, M.; Ano, Y.; Chatani, N. Org. Lett. 2009, 11, 3250
13. Ni: Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2009, 11, 4156
14. Cu: Besseliévre, F.; Piguel, S. Angew. Chem., Int. Ed. 2009, 48, 9553
15. Kawano, T.; Matsuyama, N.; Hirano, K.; Satoh, T.; Miura, M. J. Org. Chem. 2010, 75, 1764
16. Au: Brand, J. P.; Charpentier, J.; Waser, J. Angew. Chem., Int. Ed. 2009, 48, 9346
17. See also: Dudnik, A. S.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2096
18. Kitahara, M.; Hirano, K.; Tsurugi, H.; Satoh, T.; Miura, M. Chem.- Eur. J. 2010, 16, 1772
19. A gold-mediated process is also known: Fuchita, Y.; Utsunomiya, Y.; Yasutake, M. J. Chem. Soc., Dalton Trans. 2001, 2330
20. During the preparation of this manuscript, two successful examples of the catalytic direct coupling of arenes with terminal alkynes have been reported. Au: de Haro, T.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 1512
21. Cu: Wei, Y.; Zhao, H.; Kan, J.; Su, W.; Hong, M. J. Am. Chem. Soc. 2010, 132, 2522
22. Kumar, D.; David, W. M.; Kerwin, S. M. Bioorg. Med. Chem. Lett. 2001, 11, 2971
23. Callstrom, M. R.; Neenan, T. X.; McCreery, R. L.; Alsmeyer, D. C. J. Am. Chem. Soc. 1990, 112, 4954
24. Dai, C.; Nguyen, P.; Marder, T. B.; Scott, A. J.; Clegg, W.; Viney, C. Chem. Commun. 1999, 2493
25. Meyer, E. A.; Castelano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210
26. Other N-based ligands such as 1,10-phenanthroline and 2,2′-bipyridine resulted in the lower yield by ca. 10% and had no influence on product selectivity. The combination of toluene and LiO- t -Bu was necessary for the reaction. The use of polar solvents and other bases such as Na- or KO- t -Bu was detrimental due to the rapid decomposition of the starting materials.
27. Shen, K.; Fu, Y.; Li, J.-N.; Liu, L.; Guo, Q.-X. Tetrahedron 2007, 63, 1568
28. Do, H.-Q.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404
29. Do, H.-Q.; Khan, R. M. K.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 15185
30. 2) complex has been reported.
31. Yao, S.; Bill, E.; Milsmann, C.; Wieghardt, K.; Driess, M. Angew. Chem., Int. Ed. 2008, 47, 7110
32. 2) complex as the active species.
33. 2) complex with arylboronic acids: Adamo, C.; Amatore, C.; Ciofini, I.; Jutand, A.; Lakmini, H. J. Am. Chem. Soc. 2006, 128, 6829
34. 2: Wilke, G.; Schott, H.; Heimbach, P. Angew. Chem., Int. Ed. Engl. 1967, 6, 92
35. Otsuka, S.; Nakamura, A.; Tatsuno, Y. J. Am. Chem. Soc. 1969, 91, 6994
36. A similar intermediate was proposed in other nickel-catalyzed reaction: Yin, W.; He, C.; Chen, M.; Zhang, H.; Lei, A. Org. Lett. 2009, 11, 709
37. Also see: Truong, T.; Alvarado, J.; Tran, L. D.; Daugulis, O. Org. Lett. 2010, 12, 1200
38. However, the mechanism involving nucleophilic attack of the nickel acetylide intermediate on azole is not completely discarded: Tobisu, M.; Hyodo, I.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070
39. 2O, the reaction proceeded to give 11ad in a somewhat lower yield (ca. 40%). We do not have an explanation for the reason at this stage. The choice of solvent was also crucial. Less polar solvent such as toluene completely failed to lead to the formation of 11ad.
40. The reaction with tri- and difluoroarenes or alkylalkynes was unsuccessful probably due to their insufficient acidities of C-H bonds.