Key mechanistic features of Ni-catalyzed C-H/C-O biaryl coupling of azoles and naphthalen-2-yl pivalates

Journal of the American Chemical Society

Volumn 136, Issue 42, 2014, Pages 14834-14844

  Xu, Huiying ^a,b   Muto, Kei ^c   Yamaguchi, Junichiro ^c   Zhao, Cunyuan ^b   Itami, Kenichiro ^c   Musaev, Djamaladdin G ^a  

^a EMORY UNIVERSITY   (United States)

^b SUN YAT SEN UNIVERSITY   (China)

^c NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; HYDROGEN; NAPHTHALENE DERIVATIVE; NICKEL; PYRROLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; LIGAND; NAPHTHALENE;

ACIDITY; ADDITION REACTION; ARTICLE; CATALYST; COVALENT BOND; OXIDATIVE COUPLING; REACTION ANALYSIS; STOICHIOMETRY; SUBSTITUTION REACTION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION;

BENZOXAZOLES; CATALYSIS; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NAPHTHALENES; NICKEL;

EID: 84908518377     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5071174     Document Type: Article

References (76)

1. (a) Zheng, C.; You, S.-L. RSC Adv. 2014, 4, 6173-6214.
2. (b) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726-11743.
3. (c) Yamaguchi, J.; Yamaguchi, A. D.; Itami, K. Angew. Chem., Int. Ed. 2012, 51, 8960-9009.
4. (d) Davies, H. M.; Manning, J. R. Nature 2008, 451, 417-424.
5. (e) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173-1193.
6. (f) Cho, S. H.; Kim, J. Y.; Kwak, J.; Chang, S. Chem. Soc. Rev. 2011, 40, 5068-5083.
7. (g) Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236-10254.
8. (h) Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902-4911.
9. (i) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169.
10. (j) Wu, N.; Song, F.; Yan, L.; Li, J.; You, J. Chem. - Eur. J. 2014, 20, 3408-3414.
11. (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174-238.
12. (b) Chiusoli, G. P.; Catellani, M.; Costa, M.; Motti, E.; Della Ca', N.; Maestri, G. Coord. Chem. Rev. 2010, 254, 456-469.
13. (c) Sierra, D.; Bhuvanesh, N.; Reibenspies, J. H.; Gladysz, J. A.; Klahn, A. H. J. Organomet. Chem. 2014, 749, 416-420.
14. (d) Han, F.-S. Chem. Soc. Rev. 2013, 42, 5270-5298.
15. Muto, K.; Yamaguchi, J.; Itami, K. J. Am. Chem. Soc. 2012, 134, 169-172.
16. Muto, K.; Yamaguchi, J.; Lei, W.; Itami, K. J. Am. Chem. Soc. 2013, 135, 16384-16387.
17. (a) Hong, X.; Liang, Y.; Houk, K. N. J. Am. Chem. Soc. 2014, 136, 2017-2025.
18. (b) Liu, L.; Zhang, S.; Chen, H.; Lv, Y.; Zhu, J.; Zhao, Y. Chem. - Asian J. 2013, 8, 2592-2595.
19. Lu, Q.; Yu, H.; Fu, Y. J. Am. Chem. Soc. 2014, 136, 8252-8260.
20. Amaike, K.; Muto, K.; Yamaguchi, J.; Itami, K. J. Am. Chem. Soc. 2012, 134, 13573-13576.
21. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford CT, 2013.
22. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101.
23. (a) Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284-298.
24. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
25. (a) Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 3032-3041.
26. (b) Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151-5158.
27. (c) Scalmani, G.; Frisch, M. J. J. Chem. Phys. 2010, 132, 114110.
28. (a) Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241.
29. (b) Zhao, Y.; Truhlar, D. G. Acc. Chem. Res. 2008, 41, 157-167.
30. (c) Zhao, Y.; Truhlar, D. G. J. Chem. Theory Comput. 2009, 5, 324-333.
31. (a) Garcia, J. J.; Brunkan, N. M.; Jones, W. D. J. Am. Chem. Soc. 2002, 124, 9547-9555.
32. (b) Yoshikai, N.; Matsuda, H.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 15258-15259.
33. (a) Quasdorf, K. W.; Antoft-Finch, A.; Liu, P.; Silberstein, A. L.; Komaromi, A.; Blackburn, T.; Ramgren, S. D.; Houk, K. N.; Snieckus, V.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 6352-6363.
34. (b) Li, Z.; Zhang, S.-L.; Fu, Y.; Guo, Q.-Z.; Liu, L. J. Am. Chem. Soc. 2009, 131, 8815-8823.
35. (a) Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754-8756.
36. (b) Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 10848-10849.
37. (a) Birkholz, M.-N.; Freixa, Z.; van Leeuwen, P. W. N. M. Chem. Soc. Rev. 2009, 38, 1099-1118.
38. (b) Clegg, W.; Eastham, G. R.; Elsegood, M. R. J.; Heaton, B. T.; Iggo, J. A.; Tooze, R. P.; Whyman, R.; Zacchini, S. Organometallics 2002, 21, 1832-1840.
39. (a) Ananikov, V. P.; Musaev, D. G.; Morokuma, K. Inorg. Chem. 2007, 34, 5390-5399.
40. (b) Ananikov, V. P.; Musaev, D. G.; Morokuma, K. Organometallics 2005, 24, 715-723.
41. (c) Ananikov, V. P.; Musaev, D. G.; Morokuma, K. J. Am. Chem. Soc. 2002, 124, 2839-2852.
42. Figg, T. M.; Wasa, M.; Yu, J.-Q.; Musaev, D. G. J. Am. Chem. Soc. 2013, 135, 14206-14214.
43. (b) Zhang, Q.; Yu, H.-Z.; Fu, Y. Organometallics 2013, 32, 4165-4173.
44. Ackermann, L. Chem. Rev. 2011, 111, 1315-1345.
45. (a) Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem. - Eur. J. 2010, 16, 2654-2672.
46. (b) Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570-14571.
47. (c) Rousseaux, S.; Gorelsky, S. I.; Chung, B. K. W.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 10692-10705.
48. (d) Dyker, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1023-1025.
49. (e) Dyker, G. J. Org. Chem. 1993, 58, 6426-6428.
50. (f) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685-4696.
51. (g) Zhao, J.; Campo, M.; Larock, R. Angew. Chem., Int. Ed. 2005, 44, 1873-1875.
52. (h) Dong, C.-G.; Hu, Q.-S. Angew. Chem., Int. Ed. 2006, 45, 2289-2292.
53. (i) Ren, H.; Li, Z.; Knochel, P. Chem. - Asian J. 2007, 2, 416-433.
54. (j) Niwa, T.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 2373-2375.
55. (k) Dong, C.-G.; Hu, Q.-S. Tetrahedron 2008, 64, 2537-2552.
56. (l) Mousseau, J. J.; Lariv-ee, A.; Charette, A. B. Org. Lett. 2008, 10, 1641-1643.
57. (m) Salcedo, A.; Neuville, L.; Zhu, J. J. Org. Chem. 2008, 73, 3600-3603.
58. (n) Niwa, T.; Yorimitsu, H.; Oshima, K. Org. Lett. 2008, 10, 4689-4691.
59. (o) Kim, H. S.; Gowrisankar, S.; Kim, S. H.; Kim, J. N. Tetrahedron Lett. 2008, 49, 3858-3861.
60. (p) Huang, Q.; Larock, R. C. Tetrahedron Lett. 2009, 50, 7235-7238.
61. (q) Wasa, M.; Engle, K. M.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 9886-9887.
62. (r) Kim, K. H.; Lee, H. S.; Kim, S. H.; Kim, S. H.; Kim, J. N. Chem. - Eur. J. 2010, 16, 2375-2380 and references cited therein.
63. Lian, B.; Zhang, L.; Chass, G. A.; Fang, D.-C. J. Org. Chem. 2013, 78, 8376-8385.
64. (a) Mateos, C.; Mendiola, J.; Carpintero, M.; Minguez, J. M. Org. Lett. 2010, 12, 4924-4927.
65. (b) Sun, H.-Y.; Gorelsky, S. I.; Stuart, D. R.; Campeau, L.-C.; Fagnou, K. J. Org. Chem. 2010, 75, 8180-8189.
66. (a) Garcia-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066-1067.
67. (b) Garcia-Cuadrado, D.; de Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2007, 129, 6880-6886.
68. (c) Kefalidis, C. E.; Baudoin, O.; Clot, E. Dalton Trans. 2010, 39, 10528-10535.
69. Mahler, J.; Persson, I. Inorg. Chem. 2012, 51, 425-438.
70. Robinson, S.; Davies, E. S.; Lewis, W.; Blake, A. J.; Liddle, S. T. Dalton Trans. 2014, 43, 4351-4360.
71. Edelmann, F. T.; Pauer, F.; Wedler, M.; Stalke, D. Inorg. Chem. 1992, 31, 4143-4146.
72. Gorelsky, S. I. Organometallics 2012, 31, 794-797.
73. ‡ = 11.5 and 9.9 kcal/mol energy barrier at the transition states TS2-Cs-clus-O and TS2-Cs-clus-N, respectively (see SI). Therefore, it is expected that the C-C coupling will directly occur from the intermediates 5-Cs-clus-O and 5-Cs-clus-N via corresponding transition states TS2-Cs-clus-O and TS2-Cs-clus-N and will lead to the product complexes 6-Cs-clus-O and 6-Cs-clus-N, respectively.
74. Shen, K.; Fu, Y.; Li, J.-N.; Liu, L.; Guo, Q.-X. Tetrahedron 2007, 63, 1568-1576.
75. (a) Ref 15b.
76. (b) Gorelsky, S. I.; Lapointe, D.; Fagnou, K. J. Org. Chem. 2011, 77, 658-668.