Organic Letters
Letter
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form the key cuprate-triazole intermediate (M ). This aryl
copper(I) intermediate is more nucleophilic than copper(I)
acetylide and it could react with the persulfur electrophile (1)
to form the triazole disulfide (4aa). This step might occur
through an oxidative addition and reductive elimination
sequence to regenerate the Cu(I) catalyst.
(6) (a) Boren, B. C.; Narayan, S.; Rasmussen, L. K.; Zhang, L.; Zhao,
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Chem., Int. Ed. 2010, 49, 31. (c) Wei, F.; Wang, W.; Ma, Y.; Tung, C.-
H.; Xu, Z. Chem. Commun. 2016, 52, 14188.
In summary, we have developed an efficient click/electro-
philic persulfuration reaction to construct triazole disulfides.
Such compounds, containing the important triazole and
disulfide moieties, are very useful in medicinal chemistry.
Notable features of this method include very simple and mild
reaction conditions, inexpensive copper catalysts, a very broad
substrate scope, and applicability in late-stage functionalization
of complex bioactive compounds. Further application of this
interrupted click reaction is in progress in our laboratory.
(
8) (a) Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev.
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(
ASSOCIATED CONTENT
Supporting Information
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314. (b) Worrell, B. T.; Hein, J. E.; Fokin, V. V. Angew. Chem., Int. Ed.
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(
(
(
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CCDC 1825670 contains the supplementary crystallographic
Crystallographic Data Centre, 12 Union Road, Cambridge CB2
(
Yan, J.; Ding, K. Org. Lett. 2012, 14, 3332. (g) Barsoum, D. N.;
Okashah, N.; Zhang, X.; Zhu, L. J. Org. Chem. 2015, 80, 9542.
(h) Zhou, W.; Zhang, M.; Li, H.; Chen, W. Org. Lett. 2017, 19, 10.
(i) Xu, J.; Song, Q. Org. Chem. Front. 2017, 4, 938.
1EZ, U.K.; fax: +44 1223 336033.
(13) (a) Wei, F.; Li, H.; Song, C.; Ma, Y.; Zhou, L.; Tung, C.-H.; Xu,
Z. Org. Lett. 2015, 17, 2860. (b) Wang, W.; Wei, F.; Ma, Y.; Tung, C.-
H.; Xu, Z. Org. Lett. 2016, 18, 4158. (c) Wang, W.; Peng, X.; Wei, F.;
Tung, C.-H.; Xu, Z. Angew. Chem., Int. Ed. 2016, 55, 649. (d) Wei, F.;
Zhou, T.; Ma, Y.; Tung, C.-H.; Xu, Z. Org. Lett. 2017, 19, 2098.
AUTHOR INFORMATION
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(14) Jiang, C.-S.; Muller, W. E. G.; Schroder, H. C.; Guo, Y.-W.
ORCID
Chem. Rev. 2012, 112, 2179.
Notes
(15) (a) Block, E.; Bayer, T.; Naganathan, S.; Zhao, S.-H. J. Am.
Chem. Soc. 1996, 118, 2799. (b) Caldarelli, S. A.; Hamel, M.; Duckert,
J.-F.; Ouattara, M.; Calas, M.; Maynadier, M.; Wein, S.; Perigaud, C.;
́
Pellet, A.; Vial, H. J.; Peyrottes, S. J. Med. Chem. 2012, 55, 4619.
(c) Cheng, Z.; Zhang, J.; Ballou, D. P.; Williams, C. H., Jr. Chem. Rev.
The authors declare no competing financial interest.
2
011, 111, 5768. (d) Gon
F. Chem. Rev. 2014, 114, 901.
16) For a review, see: (a) Musiejuk, M.; Witt, D. Org. Prep. Proced.
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gora-Benítez, M.; Tulla-Puche, J.; Albericio,
ACKNOWLEDGMENTS
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We are grateful for financial support from the National Natural
Science Foundation of China and Shandong Province (Nos.
Int. 2015, 47, 95. For recent examples, see: (b) Mai, S.; Song, Q.
Angew. Chem., Int. Ed. 2017, 56, 7952. (c) Xiao, X.; Feng, M.; Jiang, X.
Chem. Commun. 2015, 51, 4208. (d) Xiao, X.; Feng, M.; Jiang, X.
21572118 and JQ201505), and a Tang Scholar Award from
Shandong University.
Angew. Chem., Int. Ed. 2016, 55, 14121. (e) Nicolaou, K. C.; Giguer
D.; Totokotsopoulos, S.; Sun, Y.-P. Angew. Chem., Int. Ed. 2012, 51,
28. (f) Park, C.-M.; Johnson, B. A.; Duan, J.; Park, J.-J.; Day, J. J.;
Gang, D.; Qian, W.; Xian, M. Org. Lett. 2016, 18, 904. (g) Arisawa, M.;
Yamaguchi, M. J. Am. Chem. Soc. 2003, 125, 6624.
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e,
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