Organic Letters
Letter
design and the development of multicomponent cascade reaction
involving sulfonyl azides and alkynes. Further method develop-
ment studies utilizing these unique reaction pathways are
currently under investigation in our laboratory.
(8) For selected papers utilizing copper-ketenimine intermediate II
from sulfonyl azides and alkynes, see: (a) Kumar, R.; Thorat, S. H.;
Reddy, M. S. Chem. Commun. 2016, 52, 13475−13478. (b) Shen, M.-H.;
Xu, K.; Sun, C.-H.; Xu, H.-D. Org. Lett. 2015, 17, 5598−5601.
(
c) Alford, J. S.; Davies, H. M. L. J. Am. Chem. Soc. 2014, 136, 10266−
1
0269. (d) Li, B.-S.; Yang, B.-M.; Wang, S.-H.; Zhang, Y.-Q.; Cao, X.- P.;
ASSOCIATED CONTENT
Supporting Information
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Tu, Y.-Q. Chem. Sci. 2012, 3, 1975−1979. (e) Jiang, Z.; Lu, P.; Wang, Y.
Org. Lett. 2012, 14, 6266. (f) Yao, W.; Pan, L.; Zhang, Y.; Wang, G.;
Wang, X.; Ma, C. Angew. Chem., Int. Ed. 2010, 49, 9210−9214. (g) Cho,
S. H.; Chang, S. Angew. Chem., Int. Ed. 2008, 47, 2836−2839. (h) Cho, S.
H.; Chang, S. Angew. Chem., Int. Ed. 2007, 46, 1897−1900. (i) Cui, S. L.;
Wang, J.; Wang, Y. G. Org. Lett. 2007, 9, 5023−5025. (j) Whiting, M.;
Fokin, V. V. Angew. Chem., Int. Ed. 2006, 45, 3157−3161. (k) Cassidy,
M. P.; Raushel, J.; Fokin, V. V. Angew. Chem., Int. Ed. 2006, 45, 3154−
*
S
Experimental procedures and characterization of all new
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13
compounds including H and C NMR spectra (PDF)
Crystallographic data for 4b (CIF)
3
2
157. (l) Yoo, E. J.; Bae, I.; Cho, S. H.; Han, H.; Chang, S. Org. Lett.
006, 8, 1347−1350. (m) Cho, S. H.; Yoo, E. J.; Bae, I.; Chang, S. J. Am.
AUTHOR INFORMATION
Chem. Soc. 2005, 127, 16046−16047. (n) Bae, I.; Han, H.; Chang, S. J.
Am. Chem. Soc. 2005, 127, 2038−2039.
(
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*
9) For selected papers utilizing copper-triazole intermediates
generated from alkyl/aryl azides and alkynes, see: (a) Wang, W.; Wei,
F.; Ma, Y.; Tung, C.-H.; Xu, Z. Org. Lett. 2016, 18, 4158−4161.
ORCID
(b) Wang, W.; Peng, X.; Wei, F.; Tung, C.-H.; Xu, Z. Angew. Chem., Int.
Notes
Ed. 2016, 55, 649−653. (c) Wei, F.; Wang, W.; Ma, Y.; Tung, C.-H.; Xu,
Z. Chem. Commun. 2016, 52, 14188−14199. (d) Worrell, B. T.; Ellery, S.
P.; Fokin, V. V. Angew. Chem., Int. Ed. 2013, 52, 13037−13041.
The authors declare no competing financial interest.
(
10) (a) Liu, Y.-C.; Qu, R.-Y.; Chen, Q.; Yang, J.-F.; Cong-Wei, N.;
Zhen, X.; Yang, G.-F. J. Agric. Food Chem. 2016, 64, 4845−4857.
ACKNOWLEDGMENTS
(b) Bhatt, J. D.; Chudasama, C. J.; Patel, K. D. Arch. Pharm. 2016, 349,
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7
91−800. (c) Deng, X.; Kokkonda, S.; El Mazouni, F.; White, J.;
We are grateful to the Department of Science and Technology
DST), New Delhi, India for financing under DST-INSPIRE
faculty scheme (DST/INSPIRE/04/2015/001003). We thank
Prof. M. Sasidharan, SRM University for providing laboratory
facilities. We also would like to extend our thanks to Prof.
Venugopal T. Bhat and Prof. S. Mannathan of SRM University
for their valuable suggestions.
Burrows, J. N.; Kaminsky, W.; Charman, S. A.; Matthews, D.; Rathod, P.
K.; Phillips, M. A. J. Med. Chem. 2014, 57, 5381−5394. (d) Flannery, E.
L.; Chatterjee, A. K.; Winzeler, E. A. Nat. Rev. Microbiol. 2013, 11, 849−
(
8
62. (e) Yu, W.; Goddard, C.; Clearfield, E.; Mills, C.; Xiao, T.; Guo, H.;
Morrey, J. D.; Motter, N. E.; Zhao, K.; Block, T. M.; Cuconati, A.; Xu, X.
J. Med. Chem. 2011, 54, 5660−5670. (f) Allen, J. G.; Bourbeau, M. P.;
Wohlhieter, G. E.; Bartberger, M. D.; Michelsen, K.; Hungate, R.;
Gadwood, R. C.; Gaston, R. D.; Evans, B.; Mann, L. W.; Matison, M. E.;
Schneider, S.; Huang, X.; Yu, D.; Andrews, P. S.; Reichelt, A.; Long, A.
M.; Yakowec, P.; Yang, E. Y.; Lee, T. A.; Oliner, J. D. J. Med. Chem. 2009,
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