Organic Letters
Letter
(2) (a) Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 633.
(13) For reviews, see: (a) Wan, J.-P.; Gao, Y. Chem. Rec. 2016, 16,
1164. (b) Cao, S.; Jing, Y.; Liu, Y.; Wan, J.-P. Youji Huaxue 2014, 34,
876.
(b) Huisgen, R.; Knorr, R.; Mobius, L.; Szeimies, G. Chem. Ber. 1965,
̈
98, 4014.
(14) During the preparation of this manuscript, Dehaen and co-
workers reported the synthesis of similar 1,4-disubstituted 1,2,3-
triazoles via the reactions of N,N-dimethyl enaminones and organo
azides: Thomas, J.; Goyvaerts, V.; Liekens, S.; Dehaen, W. Chem. - Eur.
J. 2016, 22, 9966.
(3) (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B.
Angew. Chem., Int. Ed. 2002, 41, 2596. (b) Lee, L. V.; Mitchell, M. L.;
Huang, S. J.; Fokin, V. V.; Sharpless, K. B.; Wong, C. H. J. Am. Chem.
Soc. 2003, 125, 9588.
(4) Tornøe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002,
(15) Liu, Y.; Zhou, R.; Wan, J.-P. Synth. Commun. 2013, 43, 2475.
(16) CCDC 1504366 contains the supplementary crystallographic
data for this paper (4b). These data can be obtained free of charge
from the Cambridge Crystallographic Data Centre via www.ccdc.cam.
(17) (a) Regitz, M. Ann. 1964, 676, 101. (b) Regitz, M. Tetrahedron
Lett. 1964, 5, 1403. (c) Regitz, M. Angew. Chem., Int. Ed. Engl. 1967, 6,
733. (d) Wang, Z. Regitz Diazo Transfer. Comprehensive Organic Name
Reactions and Reagents 2010, 524, 2322−2325.
67, 3057.
(5) (a) Yamamoto, K.; Bruun, T.; Kim, J. Y.; Zhang, L.; Lautens, M.
Org. Lett. 2016, 18, 2644. (b) Barman, M. K.; Sinha, A. K.; Nembenna,
S. Green Chem. 2016, 18, 2534. (c) Chassaing, S.; Beneteau, V.; Pale,
́ ́
P. Catal. Sci. Technol. 2016, 6, 923. (d) Hassan, S.; Muller, T. J. J. Adv.
Synth. Catal. 2015, 357, 617. (e) Tasca, E.; Sorella, G. L.; Sperni, L.;
Strukul, G.; Scarso, A. Green Chem. 2015, 17, 1414. (f) Xiong, X.; Cai,
L.; Jiang, Y.; Han, H. ACS Sustainable Chem. Eng. 2014, 2, 765.
(g) Roy, S.; Chatterjee, T.; Islam, S. M. Green Chem. 2013, 15, 2532.
(h) Sau, S. C.; Roy, S. R.; Sen, T. K.; Mullangi, D.; Mandal, S. K. Adv.
Synth. Catal. 2013, 355, 2982. (i) Song, T.; Li, L.; Zhou, W.; Zhang,
Z.-J.; Deng, Y.; Xu, Z.; Xu, L.-W. Chem. - Eur. J. 2015, 21, 554.
(6) (a) Ramasastry, S. S. V. Angew. Chem., Int. Ed. 2014, 53, 14310.
(b) Li, W.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 14186.
(c) Thomas, J.; John, J.; Parekh, N.; Dehaen, W. Angew. Chem., Int. Ed.
2014, 53, 10155. (d) Wan, J.-P.; Cao, S.; Liu, Y. J. Org. Chem. 2015,
80, 9028. (e) Li, W.; Du, Z.; Zhang, K.; Wang, J. Green Chem. 2015,
17, 781. (f) Bai, H.-W.; Cai, Z.-J.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2015,
17, 2898. (g) Hu, Q.; Liu, Y.; Deng, X.; Li, Y.; Chen, Y. Adv. Synth.
Catal. 2016, 358, 1689. (h) Agard, N. J.; Prescher, J. A.; Bertozzi, C. R.
J. Am. Chem. Soc. 2004, 126, 15046.
(7) (a) Chen, Z.; Yan, Q.; Liu, Z.; Xu, Y.; Zhang, Y. Angew. Chem.,
Int. Ed. 2013, 52, 13324. (b) Li, Y.-J.; Li, X.; Zhang, S.-X.; Zhao, Y.-L.;
Liu, Q. Chem. Commun. 2015, 51, 11564. (c) Ahamad, S.; Kant, R.;
Mohanan, K. Org. Lett. 2016, 18, 280. (d) Wan, J.-P.; Hu, D.; Liu, Y.;
Sheng, S. ChemCatChem 2015, 7, 901.
(8) (a) Katritzky, A. R.; Singh, S. K. J. Org. Chem. 2002, 67, 9077.
́
(b) Wang, Z.-X.; Qin, H.-L. Chem. Commun. 2003, 2450. (c) Krasinski,
A.; Fokin, V. V.; Sharpless, K. B. Org. Lett. 2004, 6, 1237. (d) Lee, B.-
Y.; Park, S. R.; Jeon, H. B.; Kim, K. S. Tetrahedron Lett. 2006, 47, 5105.
(e) Spiteri, C.; Moses, J. E. Angew. Chem., Int. Ed. 2010, 49, 31.
(f) Kwok, S. W.; Fotsing, J. R.; Fraser, R. J.; Rodionov, V. O.; Fokin, V.
V. Org. Lett. 2010, 12, 4217. (g) Zhou, Y.; Lecourt, T.; Micouin, L.
Angew. Chem., Int. Ed. 2010, 49, 2607. (h) Danence, L. J. T.; Gao, Y.;
Li, M.; Huang, Y.; Wang, J. Chem. - Eur. J. 2011, 17, 3584. (i) Zhang,
Z.; Zhou, Q.; Ye, F.; Xia, Y.; Wu, G.; Hossain, M. L.; Zhang, Y.; Wang,
J. Adv. Synth. Catal. 2015, 357, 2277. (j) Chen, Y.; Nie, G.; Zhang, Q.;
Ma, S.; Li, H.; Hu, Q. Org. Lett. 2015, 17, 1118.
(9) For reviews on organo azide synthesis, see: (a) Scriven, E. F. V.;
Turnbull, K. Chem. Rev. 1988, 88, 297. (b) Brase, S.; Gil, C.; Knepper,
̈
K.; Zimmermann, V. Angew. Chem., Int. Ed. 2005, 44, 5188.
(10) (a) Appukkuttan, P.; Dehaen, W.; Fokin, V. V.; Van der Eycken,
E. Org. Lett. 2004, 6, 4223. (b) Sharghi, H.; Khalifeh, R.; Doroodmand,
M. M. Adv. Synth. Catal. 2009, 351, 207. (c) Tavassoli, M. A.;
Landarani-Isfahani; Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.;
Mohammadpoor-Baltork, I. ACS Sustainable Chem. Eng. 2016, 4, 1454.
(d) Johansson, J. R.; Lincoln, P.; Norden, B.; Kann, N. J. Org. Chem.
́
2011, 76, 2355. (e) Xiong, X.; Cai, L. Catal. Sci. Technol. 2013, 3,
1301.
(11) (a) Yoo, E. Y.; Ahlquist, M.; Kim, S. H.; Bae, I.; Fokin, V. V.;
Sharpless, K. B.; Chang, S. Angew. Chem., Int. Ed. 2007, 46, 1730.
(b) Raushel, J.; Fokin, V. V. Org. Lett. 2010, 12, 4952. (c) Ramachary,
D. B.; Ramakumar, K.; Narayana, V. V. Chem. - Eur. J. 2008, 14, 9143.
(d) Amantini, D.; Fringuelli, F. O.; Piermatti; Pizzo, F.; Zunino, E.;
Vaccaro, L. J. Org. Chem. 2005, 70, 6526. (e) Barluenga, J.; Valdes
́
, C.;
Beltran, G.; Escribano, M.; Aznar, F. Angew. Chem., Int. Ed. 2006, 45,
́
6893. (f) Quan, X.-J.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. Org. Lett.
2014, 16, 5728.
(12) Cheng, G.; Zeng, X.; Shen, J.; Wang, X.; Cui, X. Angew. Chem.,
Int. Ed. 2013, 52, 13265.
D
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