Organic Letters
Letter
(e) Heinrich, M. R.; Wetzel, A.; Kirschstein, M. Org. Lett. 2007, 9,
3833. (f) Callonnec, F. L.; Fouquet, E.; Felpin, F. X. Org. Lett. 2011,
13, 2646.
(5) (a) Balz, G.; Schiemann, G. Ber. Dtsch. Chem. Ges. B 1927, 60,
1186. (b) Laali, K. K.; Gettwert, V. J. J. Fluorine Chem. 2001, 107, 31.
(6) (a) Sandmeyer, T. Ber. Dtsch. Chem. Ges. 1884, 17, 1633.
(b) Liu, Q.; Sun, B.; Liu, Z.; Kao, Y.; Dong, B. W.; Jiang, S. D.; Li, F.;
Liu, G.; Yang, Y.; Mo, F. Chem. Sci. 2018, 9, 8731. (c) Leas, D. A.;
Dong, Y.; Vennerstrom, J. L.; Stack, D. E. Org. Lett. 2017, 19, 2518.
rongalite acts simultaneously as the radical initiator and
reducing agent in this reaction, while aryldiazonium tetra-
fluoroborates serve as dual synthons. This pyrazoles synthesis
is green and practicable, with wide substance scope. Further
studies to develop new multicomponent radical tandem
reactions by using rongalite as a versatile reagent for other
important heterocycles are being explored in our lab.
ASSOCIATED CONTENT
* Supporting Information
(d) Vanicek, S.; Kopacka, H.; Wurst, K.; Muller, T.; Hassenruck, C.;
̈ ̈
Winter, R. F.; Bildstein, B. Organometallics 2016, 35, 2101.
■
S
(7) (a) Naveen, N.; Sengupta, S.; Chandrasekaran, S. J. Org. Chem.
2018, 83, 3562. (b) Wang, W.; Zhang, S.; Zhao, H.; Wang, S. Org.
Biomol. Chem. 2018, 16, 8565. (c) Zhou, K.; Zhang, J.; Qiu, G.; Wu, J.
Org. Lett. 2019, 21, 275. (d) Chatterjee, T.; Bhadra, S.; Ranu, B. C.
Green Chem. 2011, 13, 1837.
(8) (a) Wang, S.; Qiu, D.; Mo, F.; Zhang, Y.; Wang, J. J. Org. Chem.
2016, 81, 11603. (b) He, Y.; Wu, H.; Toste, F. D. Chem. Sci. 2015, 6,
1194.
The Supporting Information is available free of charge on the
Experimental procedures, product characterizations,
1
crystallographic data, and copies of the H and 13C
(9) (a) Yu, J.; Zhang, L.; Yan, G. Adv. Synth. Catal. 2012, 354, 2625.
(b) Mo, F.; Jiang, Y.; Qiu, D.; Zhang, Y.; Wang, J. Angew. Chem., Int.
Ed. 2010, 49, 1846. (c) Zhu, C.; Yamane, M. Org. Lett. 2012, 14,
4560. (d) Qiu, D.; Jin, L.; Zheng, Z.; Meng, H.; Mo, F.; Wang, X.;
Zhang, Y.; Wang, J. J. Org. Chem. 2013, 78, 1923.
(10) (a) Frank, R. L.; Phillips, R. R. J. Am. Chem. Soc. 1949, 71,
2804. (b) Yao, H. C.; Resnick, P. J. Am. Chem. Soc. 1962, 84, 3514.
(c) Ramanathan, M.; Wang, Y. H.; Liu, S. T. Org. Lett. 2015, 17, 5886.
(11) Yu, X. L.; Chen, J. R.; Chen, D. Z.; Xiao, W. Chem. Commun.
2016, 52, 8275.
(12) (a) Shao, Y.; Zheng, H.; Qian, J.; Wan, X. Org. Lett. 2018, 20,
2412. (b) Deng, G. B.; Li, H. B.; Yang, X. H.; Song, R. J.; Hu, M.; Li,
J. H. Org. Lett. 2016, 18, 2012.
(13) Kindt, S.; Wicht, K.; Heinrich, M. R. Org. Lett. 2015, 17, 6122.
(14) An, Y.; Wu, J. Org. Lett. 2017, 19, 6028.
Accession Codes
CCDC 1888713 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
AUTHOR INFORMATION
■
Corresponding Author
ORCID
Notes
(15) Liu, F.; Wang, J. Y.; Zhou, P.; Li, G.; Hao, W. J.; Tu, S. J.; Jiang,
B. Angew. Chem., Int. Ed. 2017, 56, 15570.
(16) For general reviews on the synthesis of pyrazoles and its
derivatives, see: (a) Janin, Y. L. Chem. Rev. 2012, 112, 3924.
The authors declare no competing financial interest.
́
́
́
(b) Fustero, S.; Sanchez-Rosello, M.; Barrio, P.; Simon-Fuentes, A.
Chem. Rev. 2011, 111, 6984.
ACKNOWLEDGMENTS
■
We are grateful to the National Natural Science Foundation of
China (Grant Nos. 21472056, 21602070, and 21772051) for
financial support. This work was also supported by the 111
Project B17019.
(17) (a) Weber, A.; Casini, A.; Heine, A.; Kuhn, D.; Supuran, C. T.;
Scozzafava, A.; Klebe, G. J. Med. Chem. 2004, 47, 550. (b) Habeeb, A.
G.; Praveen Rao, P. N.; Knaus, E. E. J. Med. Chem. 2001, 44, 3039.
(c) Liu, J. J.; Sun, J.; Fang, Y. B.; Yang, Y. A.; Jiao, R. H.; Zhu, H. L.
Org. Biomol. Chem. 2014, 12, 998. (d) Abdel-Magid, A. F. ACS Med.
Chem. Lett. 2014, 5, 730.
(18) (a) Sui, Z.; Guan, J.; Ferro, M. P.; McCoy, K.; Wachter, M. P.;
Murray, W. V.; Singer, M.; Steber, M.; Ritchie, D. M.; Argentieri, D.
C. Bioorg. Med. Chem. Lett. 2000, 10, 601. (b) Raulf, M.; Konig, W.
REFERENCES
■
(1) Reviews on aryldiazonium salts: (a) Galli, C. Chem. Rev. 1988,
88, 765. (b) Roglans, A.; Pla-Quintana, A.; Moreno-Man
Rev. 2006, 106, 4622. (c) Hari, D. P.; Konig, B. Angew. Chem., Int. Ed.
2013, 52, 4734. (d) Mo, F.; Qiu, D.; Zhang, Y.; Wang, J. Acc. Chem.
Res. 2018, 51, 496. (e) Felpin, F. X.; Sengupta, S. Chem. Soc. Rev.
2019, 48, 1150.
(2) For recent work on aryldiazonium salts, see: (a) Fu, W.; Xu, F.;
Fu, Y.; Zhu, M.; Yu, J.; Xu, C.; Zou, D. J. Org. Chem. 2013, 78, 12202.
(b) Zheng, D.; An, Y.; Li, Z.; Wu, J. Angew. Chem., Int. Ed. 2014, 53,
2451. (c) Zheng, D.; Yu, J.; Wu, J. Angew. Chem., Int. Ed. 2016, 55,
11925−11929. (d) Qin, X. Y.; He, L.; Li, J.; Hao, W. J.; Tu, S. J.;
Jiang, B. Chem. Commun. 2019, 55, 3227. (e) Liu, S.; Chen, K.; Hao,
W. J.; Tu, X. C.; Tu, S. J.; Jiang, B. J. Org. Chem. 2019, 84, 1964.
(f) Wang, A. F.; Hao, W. J.; Zhu, Y. L.; Li, G.; Zhou, P.; Tu, S. J.;
Jiang, B. ACS Omega 2018, 3, 1482. (g) Zhou, K.; Zhang, J.; Qiu, G.;
Wu, J. Org. Lett. 2019, 21, 275. (h) Liu, T.; Zhou, W.; Wu, J. Org. Lett.
2017, 19, 6638.
̃
as, M. Chem.
̈
̈
Immunopharmacology 1990, 19, 103. (c) Hearn, L.; Derry, S.; Moore,
R. A. Cochrane Database Syst. Rev. 2016, 4, CD011421.
(19) (a) Kotha, S.; Khedkar, P. Chem. Rev. 2012, 112, 1650.
(b) Wang, Z. L.; Tang, R. Y.; Luo, P. S.; Deng, C. L.; Zhong, P.; Li, J.
H. Tetrahedron 2008, 64, 10670. (c) Wang, M.; Tang, B. C.; Wang, J.
G.; Xiang, J. C.; Guan, A. Y.; Huang, P. P.; Guo, W. Y.; Wu, Y. D.;
Wu, A. X. Chem. Commun. 2018, 54, 7641. (d) Chandrasekaran, S.;
Venkateswarlu, C. Synthesis 2015, 47, 395.
(3) (a) Pschorr, R. Ber. Dtsch. Chem. Ges. 1896, 29, 496. (b) Leake,
P. H. Chem. Rev. 1956, 56, 27.
(4) (a) Meerwein, H.; Buchner, E.; van Emster, K. J. Prakt. Chem.
̈
1939, 152, 237. (b) Rondestvedt, C. S. J. Org. Chem. 1977, 42, 2618−
̈
2620. (c) Yao, C. J.; Sun, Q.; Rastogi, N.; Konig, B. ACS Catal. 2015,
5, 2935. (d) Ni, Z.; Huang, X.; Pan, Y. Org. Lett. 2016, 18, 2612.
D
Org. Lett. XXXX, XXX, XXX−XXX