Page 7 of 8
Journal of the American Chemical Society
Zhu, L. J. Am. Chem. Soc. 2006, 128, 15048; (l) Li, Z.; Li, C.-J. J. Am.
Chem. Soc. 2004, 126, 11810.
(4) He, K.-H.; Li, Y. ChemSusChem 2014, 7, 2788.
netic studies had been presented, which indicated that H2 is gener-
ated directly from the substrates and the interaction between the
cobalt catalyst and proton is the rate-limiting process. The trans-
formation holds significant potential for the applications to a se-
ries of organic reactions.
1
2
3
4
5
6
7
8
(5) (a) Zeug, N.; Buecheler, J.; Kisch, H. J. Am. Chem. Soc. 1985, 107,
1459; (b) Mitkina, T.; Stanglmair, C.; Setzer, W.; Gruber, M.; Kisch, H.;
Konig, B. Org. Biomol. Chem. 2012, 10, 3556; (c) Meng, Q.-Y.; Zhong,
J.-J.; Liu, Q.; Gao, X.-W.; Zhang, H.-H.; Lei, T.; Li, Z.-J.; Feng, K.; Chen,
B.; Tung, C.-H.; Wu, L.-Z. J. Am. Chem. Soc. 2013, 135, 19052; (d)
Zhong, J. J.; Meng, Q. Y.; Liu, B.; Li, X. B.; Gao, X. W.; Lei, T.; Wu, C.
J.; Li, Z. J.; Tung, C. H.; Wu, L. Z. Org. Lett. 2014, 16, 1988; (e) Gao, X.-
W.; Meng, Q.-Y.; Li, J.-X.; Zhong, J.-J.; Lei, T.; Li, X.-B.; Tung, C.-H.;
Wu, L.-Z. ACS Catal. 2015, 2391.
(6) Li, X. B.; Li, Z. J.; Gao, Y. J.; Meng, Q. Y.; Yu, S.; Weiss, R. G.;
Tung, C. H.; Wu, L. Z. Angew. Chem. Int. Ed. 2014, 53, 2085.
(7) He, R.; Huang, Z.-T.; Zheng, Q.-Y.; Wang, C. Angew. Chem. Int. Ed.
2014, 53, 4950.
ASSOCIATED CONTENT
Supporting Information
The experimental procedure, characterization data, and copies of
1H and 13C NMR spectra. This material is available free of charge
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
AUTHOR INFORMATION
Corresponding Author
(8) Zhou, A.-X.; Mao, L.-L.; Wang, G.-W.; Yang, S.-D. Chem. Comm.
2014, 50, 8529.
(9) (a) Sun, Q.; Wu, R.; Cai, S.; Lin, Y.; Sellers, L.; Sakamoto, K.; He, B.;
Peterson, B. R. J. Med. Chem. 2011, 54, 1126; (b) Mathis, C. A.; Wang,
Y.; Holt, D. P.; Huang, G.-F.; Debnath, M. L.; Klunk, W. E. J. Med.
Chem. 2003, 46, 2740; (c) Yoshida, H.; Nakao, R.; Nohta, H.; Yamaguchi,
M. Dyes. Pigm. 2000, 47, 239; (d) Yamamoto, K.; Fujita, M.; Tabashi, K.;
Kawashima, Y.; Kato, E.; Oya, M.; Iso, T.; Iwao, J. J. Med. Chem. 1988,
31, 919.
(10) (a) Cheng, Y.; Peng, Q.; Fan, W.; Li, P. J. Org. Chem. 2014, 79,
5812; (b) Feng, E.; Huang, H.; Zhou, Y.; Ye, D.; Jiang, H.; Liu, H. J.
Comb. Chem. 2010, 12, 422; (c) Jaseer, E. A.; Prasad, D. J. C.; Dandapat,
A.; Sekar, G. Tetrahedron Lett 2010, 51, 5009; (d) Saha, D.; Adak, L.;
Ranu, B. C. Tetrahedron Lett 2010, 51, 5624; (e) Bose, D. S.; Idrees, M.
J. Org. Chem. 2006, 71, 8261; (f) Bose, D. S.; Idrees, M. Tetrahedron Lett
2007, 48, 669; (g) Cheng, Y.; Yang, J.; Qu, Y.; Li, P. Org. Lett. 2011, 14,
98; (h) Inamoto, K.; Hasegawa, C.; Hiroya, K.; Doi, T. Org. Lett. 2008,
10, 5147; (i) Wang, H.; Wang, L.; Shang, J.; Li, X.; Wang, H.; Gui, J.;
Lei, A. Chem. Commun. 2012, 48, 76.
aiwenlei@whu.edu.cn; lzwu@mail.ipc.ac.cn
Notes
The authors declare no competing financial interests.
ACKNOWLEDGMENT
This work was supported by the 973 Program (2011CB808600,
2012CB725302, 2013CB834804), the National Natural Science
Foundation of China (21390400, 21272180, 21302148, 2109343
and 21402217), and the Research Fund for the Doctoral Program
of Higher Education of China (20120141130002) and the Minis-
try of Science and Technology of China (2012YQ120060) and the
Program for Changjiang Scholars and Innovative Research Team
in University (IRT1030).The Program of Introducing Talents of
Discipline to Universities of China (111 Program) is also appreci-
ated.
(11) Jeletic, M. S.; Mock, M. T.; Appel, A. M.; Linehan, J. C. J. Am.
Chem. Soc. 2013, 135, 11533.
(12) Mortimer, C. G.; Wells, G.; Crochard, J.-P.; Stone, E. L.; Bradshaw,
T. D.; Stevens, M. F. G.; Westwell, A. D. J. Med. Chem. 2006, 49, 179;
(13) Zhong, J.-J.; Wu, C.-J.; Meng, Q.-Y.; Gao, X.-W.; Lei, T.; Tung, C.-
H.; Wu, L.-Z. Adv. Synth. Catal. 2014, 356, 2846.
REFERENCES
(1) (a) Lee, C.-F.; Liu, Y.-C.; Badsara, S. S. Chem. Asian. J. 2014, 9, 706;
(b) Beletskaya, I. P.; Ananikov, V. P. Chem. Rev. 2011, 111, 1596; (c)
Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147; (d) Monnier,
F.; Taillefer, M. Angew. Chem. Int. Ed. 2009, 48, 6954; (e) Beccalli, E.
M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107,
5318; (f) Kondo, T.; Mitsudo, T.-a. Chem. Rev. 2000, 100, 3205.
(14) Juris, A.; Balzani, V.; Belser, P.; von Zelewsky, A. Helv. Chim. Acta.
1981, 64, 2175.
(15) (a) Bock, C. R.; Connor, J. A.; Gutierrez, A. R.; Meyer, T. J.;
Whitten, D. G.; Sullivan, B. P.; Nagle, J. K. J. Am. Chem. Soc. 1979, 101,
4815; (b) Kalyanasundaram, K. Coord. Chem. Rev. 1982, 46, 159; (c)
Pavlishchuk, V. V.; Addison, A. W. Inorg. Chim. Acta. 2000, 298, 97; (d)
Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Chem. Rev. 2013, 113,
5322.
(16) Du, P.; Schneider, J.; Luo, G.; Brennessel, W. W.; Eisenberg, R.
Inorg. Chem. 2009, 48, 4952.
(17) (a) Artero, V.; Chavarot-Kerlidou, M.; Fontecave, M. Angew. Chem.
Int. Ed. 2011, 50, 7238; (b) Dempsey, J. L.; Brunschwig, B. S.; Winkler,
J. R.; Gray, H. B. Acc. Chem. Res. 2009, 42, 1995; (c) Du, P.; Knowles,
K.; Eisenberg, R. J. Am. Chem. Soc. 2008, 130, 12576.
(2) (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457; (b) Hiyama,
T.; Obayashi, M.; Mori, I.; Nozaki, H. J. Org. Chem. 1983, 48, 912; (c)
Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636; (d) King, A.
O.; Okukado, N.; Negishi, E.-i. J. Chem. Soc., Chem. Commun. 1977, 683.
(3) (a) Liu, C.; Liu, D.; Lei, A. Acc. Chem. Res. 2014, 47, 3459; (b)
Girard, S. A.; Knauber, T.; Li, C. J. Angew. Chem. Int. Ed. 2014, 53, 74;
(c) Wang, J.; Liu, C.; Yuan, J.; Lei, A. Angew. Chem. Int. Ed. 2013, 52,
2256; (d) Liu, Q.; Jackstell, R.; Beller, M. Angew. Chem. Int. Ed. 2013,
52, 13871; (e) Liu, D.; Liu, C.; Li, H.; Lei, A. Angew. Chem. Int. Ed.
2013, 52, 4453; (f) Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012,
41, 3464; (g) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111,
1780; (h) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Comm. 2010, 46, 677; (i)
Chen, M.; Zheng, X.; Li, W.; He, J.; Lei, A. J. Am. Chem. Soc. 2010, 132,
4101; (j) Yin, W.; He, C.; Chen, M.; Zhang, H.; Lei, A. Org. Lett. 2009,
11, 709; (k) Zhao, Y.; Wang, H.; Hou, X.; Hu, Y.; Lei, A.; Zhang, H.;
ACS Paragon Plus Environment