Organic Letters
Letter
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whole reaction process, so that the crude product could be
obtained simply by filtration or centrifugal separation.
In summary, a highly efficient catalytic [Cu]/O2 system has
been developed for the assembly of 1,2,4-triazoles and 1,3,5-
triazines from amidines through a catalytic C(sp3)−H oxidative
functionalization. A wide range of the two three-nitrogen-
containing heterocycles can be readily accessed by using three
different reaction partners: trialkylamines, DMSO, and DMF.
The method significantly provides synthetic divergence and
flexibility for the synthesis of multinitrogen heterocycles from
amidines. These all make the protocol attractive and fascinating.
The mechanistic investigation and further application of this
method in the synthesis of more complex compounds are
currently underway in our laboratory.
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ASSOCIATED CONTENT
* Supporting Information
■
S
(9) Brough, P.; Gambarelli, S.; Jacquot, J.-F.; Grand, A.; Pcaut, J.; Rey,
P. Chem.Eur. J. 2011, 17, 11250.
General experimental procedure and characterization data of the
products. The Supporting Information is available free of charge
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AUTHOR INFORMATION
Corresponding Authors
■
Author Contributions
∥H.H. and W.G. contributed equally.
Notes
10429. (e) Boess, E.; Sureshkumar, D.; Sud, A.; Wirtz, C.; Fares
̀
, C.;
Klussmann, M. J. Am. Chem. Soc. 2011, 133, 8106.
The authors declare no competing financial interest.
(12) (a) Wan, C. F.; Zhang, J. T.; Wang, S. J.; Fan, J. M.; Wang, Z. Y.
Org. Lett. 2010, 12, 2338. (b) Wan, C. F.; Gao, L. F.; Wang, Q.; Zhang, J.
T.; Wang, Z. Y. Org. Lett. 2010, 12, 3902. (c) Zeng, L. Y.; Yi, W. B.; Cai,
C. Eur. J. Org. Chem. 2012, 2012, 559. (d) Han, B.; Yang, X. L.; Wang, C.;
Bai, Y. W.; Pan, T. C.; Chen, X.; Yu, W. J. Org. Chem. 2011, 77, 1136.
(e) Han, B.; Wang, C.; Han, R. F.; Yu, W.; Duan, X. Y.; Fang, R.; Yang, X.
L. Chem. Commun. 2011, 47, 7818. (f) Yan, Y. Z.; Wang, Z. Y. Chem.
Commun. 2011, 47, 9513. (g) Jiang, H.; Huang, H.; Cao, H.; Qi, C. Org.
Lett. 2010, 12, 5561. (h) Huang, H.; Ji, X.; Wu, W.; Jiang, H. Adv. Synth.
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J. Org. Chem. 2013, 78, 3774.
ACKNOWLEDGMENTS
■
This work was supported by the National Basic Research
Program of China (973 Program) (2011CB808600), the
National Natural Science Foundation of China (21172076 and
21420102003), the China Postdoctoral Science Foundation
Funded Project (2014M562165), Guangdong Natural Science
Foundation (10351064101000000), and Jiangxi Natural Science
Foundation (20141BBG70070 and 20151BAB203011).
(13) (a) Jiang, H.; Li, X.; Pan, X.; Zhou, P. Pure. Appl. Chem. 2012, 84,
553. (b) Li, X.; He, L.; Chen, H.; Wu, W.; Jiang, H. J. Org. Chem. 2013,
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(14) GC yield of 4j was given. No product could be obtained after flash
column chromatography, which was probably due to the instability or
the volatility of this compound.
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