Theoretical mechanistic study of novel Ni(0)-catalyzed [6 - 2 + 2] cycloaddition reactions of isatoic anhydrides with alkynes: Origin of facile decarboxylation

Organometallics

Volumn 32, Issue 24, 2013, Pages 7564-7574

  Guan, Wei ^a   Sakaki, Shigeyoshi ^a   Kurahashi, Takuya ^b   Matsubara, Seijiro ^b  

^a KYOTO UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CARBON DIOXIDE; CARBOXYLATION; CATALYSIS; CYCLOADDITION; HYDROCARBONS; PHOSPHORUS COMPOUNDS;

CATALYTIC REACTIONS; CYCLOADDITION REACTION; DECARBOXYLATIVE COUPLINGS; ELECTRONIC PROCESS; ELEMENTARY PROCESS; OXIDATIVE ADDITIONS; REDUCTIVE ELIMINATION; THEORETICAL MECHANISTIC STUDIES;

NICKEL;

EID: 84896522909     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om401061s     Document Type: Article

References (44)

1. Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications, 2 nd ed.; Wiley-VCH: Weinheim, Germany, 2003.
2. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127
3. Rodríguez, N.; Goossen, L. J. Chem. Soc. Rev. 2011, 40, 5030
4. Zhang, S.-L.; Fu, Y.; Shang, R.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2010, 132, 638
5. Hu, P.; Zhang, M.; Jie, X.-M.; Su, W.-P. Angew. Chem., Int. Ed. 2012, 51, 227
6. Choe, J.; Yang, J.; Park, K.; Palani, T.; Lee, S. Tetrahedron Lett. 2012, 53, 6908
7. Hu, P.; Shang, Y.-P.; Su, W.-P. Angew. Chem., Int. Ed. 2012, 51, 5945
8. Weaver, J. D.; Recio, A., III; Grenning, A. J.; Tunge, J. A. Chem. Rev. 2011, 111, 1846
9. Knight, J. G.; Tchabanenko, K.; Stoker, P. A.; Harwood, S. J. Tetrahedron Lett. 2005, 46, 6261
10. Knight, J. G.; Stoker, P. A.; Tchabanenko, K.; Harwood, S. J.; Lawrie, K. W. M. Tetrahedron 2008, 64, 3744
11. Wang, C.; Tunge, J. A. Org. Lett. 2006, 8, 3211
12. Wang, C.; Tunge, J. A. J. Am. Chem. Soc. 2008, 130, 8118
13. Shintani, R.; Park, S.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 14866
14. Shintani, R.; Park, S.; Shirozu, F.; Murakami, M.; Hayashi, T. J. Am. Chem. Soc. 2008, 130, 16174
15. Shintani, R.; Tsuji, T.; Park, S.; Hayashi, T. J. Am. Chem. Soc. 2010, 132, 7508
16. Shintani, R.; Murakami, M.; Hayashi, T. Org. Lett. 2009, 11, 457
17. Shintani, R.; Murakami, M.; Hayashi, T. J. Am. Chem. Soc. 2007, 129, 12356
18. Inami, T.; Baba, Y.; Kurahashi, T.; Matsubara, S. Org. Lett. 2011, 13, 1912
19. Ochi, Y.; Kurahashi, T.; Matsubara, S. Org. Lett. 2011, 13, 1374
20. Maizuru, N.; Inami, T.; Kurahashi, T.; Matsubara, S. Org. Lett. 2011, 13, 1206
21. Fujiwara, K.; Kurahashi, T.; Matsubara, S. Org. Lett. 2010, 12, 4548
22. Ooguri, A.; Nakai, K.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2009, 131, 13194
23. Kajita, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2008, 130, 17226
24. Kajita, Y.; Matsubara, S.; Kurahashi, T. J. Am. Chem. Soc. 2008, 130, 6058
25. Yoshino, Y.; Kurahashi, T.; Matsubara, S. J. Am. Chem. Soc. 2009, 131, 7494
26. Andersson, M. I.; MacGowan, A. P. J. Antimicrob. Chemother. 2003, 51, 1
27. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
28. Barone, V.; Cossi, M. J. Phys. Chem. A 1998, 102, 1995
29. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669
30. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999
31. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299
32. Couty, M.; Hall, M. B. J. Comput. Chem. 1996, 17, 1359
33. Ehlers, A. W.; Böhme, M.; Dapprich, S.; Gobbi, A.; Höllwarth, A.; Jonas, V.; Köhler, K. F.; Stegmann, R.; Veldkamp, A.; Frenking, G. Chem. Phys. Lett. 1993, 208, 111
34. Mammen, M.; Shakhnovich, E. I.; Deutch, J. M.; Whitesides, G. M. J. Org. Chem. 1998, 63, 3821
35. Dolg, M.; Wedig, U.; Stoll, H.; Preuss, H. J. Chem. Phys. 1987, 86, 866
36. Martin, J. M. L.; Sundermann, A. J. Chem. Phys. 2001, 114, 3408
37. Frisch, M. J., Gaussian 09, Revision B.01; Gaussian, Inc., Wallingford, CT, 2010.
38. Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1976, 98, 7255
39. Ozawa, F.; Hikida, T.; Hayashi, T. J. Am. Chem. Soc. 1994, 116, 2844
40. Baba, H.; Suzuki, S.; Takemura, T. J. Chem. Phys. 1969, 50, 2078
41. Kato, S.; Yamabe, S.; Fukui, K. J. Chem. Phys. 1974, 60, 572
42. Dapprich, S.; Frenking, G. J. Phys. Chem. 1995, 99, 9352
43. Takagi, N.; Sakaki, S. J. Am. Chem. Soc. 2012, 134, 11749
44. Takagi, N.; Sakaki, S. J. Am. Chem. Soc. 2013, 135, 8955