Organic Letters
Letter
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radical C would react with SO2 leading to the sulfonyl radical
D. On the other hand, DABCO·(SO2)2 would reduce Cu(II) to
i
Cu(I) with the assistance of PrOH. Subsequent oxidative
addition gave rise to Cu(III) intermediate E, which would react
with the sulfonyl radical to afford a Cu(IV) intemediate F.
Finally, reductive elimination of intemediate F would provide
the desired product and regenerate the Cu(II) catalyst.
In conclusion, we have developed a simple and general
approach for the synthesis of sulfonamides via a copper-
catalyzed three-component reaction of aryldiazonium
tetrafluoroborates, DABCO·(SO2)2, and N-chloroamines. This
coupling reaction utilizes N-chloroamines as the amino source
in sulfur dioxide insertion reactions, which takes place under
mild conditions and shows broad substrate scope. Moreover,
amines can be used instead of N-chloroamines via in situ
chlorination in a one-pot, two-step process. A possible
mechanism involving a radical process and transition-metal
catalysis is proposed. This reaction also shows that the merger
of metal catalysis and a radical process is a powerful strategy in
this field.
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
■
S
Experimental procedures, characterization data, copies of
1H and 13C NMR of products (PDF)
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Author Contributions
∥F.Z. and D.Z. contributed equally.
Notes
(9) For selected examples, see: (a) Zheng, D.; An, Y.; Li, Z.; Wu, J.
Angew. Chem., Int. Ed. 2014, 53, 2451. (b) Zheng, D.; Mao, R.; Li, Z.;
Wu, J. Org. Chem. Front. 2016, 3, 359. (c) Zheng, D.; Chen, M.; Yao,
L.; Wu, J. Org. Chem. Front. 2016, 3, 985. (d) Zhou, K.; Xia, H.; Wu, J.
Org. Chem. Front. 2017, 4, 1121. (e) Yu, J.; Mao, R.; Wang, Q.; Wu, J.
Org. Chem. Front. 2017, 4, 617. (f) Liu, T.; Zheng, D.; Wu, J. Org.
Chem. Front. 2017, 4, 1079. (g) Zhang, J.; An, Y.; Wu, J. Chem. - Eur. J.
2017, 23, 9477. (h) Xiang, Y.; Kuang, Y.; Wu, J. Chem. - Eur. J. 2017,
23, 6996.
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
Financial support from the National Natural Science
Foundation of China (No. 21302051) and “1515” academic
leader team program of Hunan Agricultural University is
gratefully acknowledged. We sincerely thank Dr. Han Wang
and Mr. Xianyin Ma (Fudan University) for their kind help in
the cyclic voltammetry testing.
(10) Wang, Q.; Tang, X.-Y.; Shi, M. Angew. Chem., Int. Ed. 2016, 55,
10811.
(11) Zheng, D.; Yu, J.; Wu, J. Angew. Chem., Int. Ed. 2016, 55, 11925.
(12) (a) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Soc. Rev.
2016, 45, 2044. (b) Kawano, T.; Hirano, K.; Satoh, T.; Miura, M. J.
Am. Chem. Soc. 2010, 132, 6900. (c) Miura, T.; Morimoto, M.;
Murakami, M. Org. Lett. 2012, 14, 5214. (d) Nishikawa, M.; Inaba, Y.;
Furukawa, M. Chem. Pharm. Bull. 1983, 31, 1374. (e) Zhu, H.; Shen,
Y.; Deng, Q.; Tu, T. Chem. Commun. 2015, 51, 16573.
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