Organic Letters
Letter
the fluorinated arylhydrazones were easily used to synthesize a
fluorinated pyrazole and other nitrogen-containing compounds.
We anticipate that this new method will find wide application in
organic synthesis, medicinal chemistry, and supramolecular
chemistry.
(f) Mantenuto, S.; Mantellini, F.; Favi, G.; Attanasi, O. A. Org. Lett.
2
015, 17, 2014.
7) For selected examples, see: (a) Lebedev, A. Y.; Khartulyari, A. S.;
Voskoboynikov, A. Z. J. Org. Chem. 2005, 70, 596. (b) Vina, D.; Del
Olmo, E.; Lopez-Perez, J. L.; San Feliciano, A. Org. Lett. 2007, 9, 525.
c) Muller, S.; List, B. Angew. Chem., Int. Ed. 2009, 48, 9975. (d) Thiel,
(
́
́
(
O. R.; Achmatowicz, M. M.; Reichelt, A.; Larsen, R. D. Angew. Chem., Int.
Ed. 2010, 49, 8395. (e) Guru, M. M.; Ali, M. A.; Punniyamurthy, T. J.
Org. Chem. 2011, 76, 5295. (f) Zhang, G.; Zhao, Y.; Ge, H.; Miao, J.
Angew. Chem., Int. Ed. 2012, 51, 8318. (g) Aljaar, N.; Conrad, J.; Beifuss,
U. J. Org. Chem. 2013, 78, 1045. (h) Martinez, A.; Webber, M. J.; Muller,
S.; List, B. Angew. Chem., Int. Ed. 2013, 52, 9486.
ASSOCIATED CONTENT
Supporting Information
■
*
S
Experimental procedures and characterization of all new
(8) (a) Negi, V. J.; Sharma, A. K.; Negi, J. S.; Ram, V. Int. J. Pharm.
Chem. 2012, 4, 100. (b) Wong, P. T.; Choi, S. K. Chem. Rev. 2015, 115,
1
13
19
3
(
388.
9) (a) Lehn, J. M. Chem. Soc. Rev. 2007, 36, 151. (b) Lygaitis, R.;
(
Getautis, V.; Grazulevicius, J. V. Chem. Soc. Rev. 2008, 37, 770. (c) Lehn,
J. M. Angew. Chem., Int. Ed. 2013, 52, 2836. (d) Su, X.; Aprahamian, I.
Chem. Soc. Rev. 2014, 43, 1963. (e) Tatum, L. A.; Su, X.; Aprahamian, I.
Acc. Chem. Res. 2014, 47, 2141.
AUTHOR INFORMATION
■
*
(
10) (a) Day, A. C.; Whiting, M. C. Org. Synth. 1988, 6, 10. (b) Stork,
G.; Benaim, J. Org. Synth. 1988, 6, 242.
11) (a) Japp, F. R.; Klingemann, F. Ber. Dtsch. Chem. Ges. 1887, 20,
Notes
(
The authors declare no competing financial interest.
2
3
3
942. (b) Japp, F. R.; Klingemann, F. Ber. Dtsch. Chem. Ges. 1887, 20,
284. (c) Japp, F. R.; Klingemann, F. Ber. Dtsch. Chem. Ges. 1887, 20,
398. (d) Burgart, Y. V.; Fokin, A. S.; Kuzueva, O. G.; Chupakhin, O. N.;
ACKNOWLEDGMENTS
■
This work was supported by the “1000 Youth Talents Plan”,
NSFC (21402098, 21421062, 21522205) and the program for
Science & Technology Innovation Talents in Universities of
Henan Province (No. 13HASTIT010 to F.S.).
Saloutin, V. I. J. Fluorine Chem. 1998, 92, 101.
(12) Reichardt, C.; Halbritter, K. Chem. Ber. 1973, 106, 1661.
(13) (a) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc.
1998, 120, 6621. (b) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am.
Chem. Soc. 1999, 121, 10251. (c) Thiel, O. R.; Achmatowicz, M. M.;
Reichelt, A.; Larsen, R. D. Angew. Chem., Int. Ed. 2010, 49, 8395.
REFERENCES
■
(
14) Xu, P.; Wang, G.; Zhu, Y.; Li, W.; Cheng, Y.; Li, S.; Zhu, C. Angew.
Chem., Int. Ed. 2016, 55, 2939.
15) Prieto, A.; Melot, R.; Bouyssi, D.; Monteiro, N. Angew. Chem., Int.
Ed. 2016, 55, 1885.
16) For selected reviews, see: (a) Giornal, F.; Pazenok, S.; Rodefeld,
L.; Lui, N.; Vors, J.; Leroux, F. R. J. Fluorine Chem. 2013, 152, 2.
b) Sloop, J. C.; Holder, C.; Henary, M. Eur. J. Org. Chem. 2015, 2015,
405.
(
1) For selected reviews, see: (a) Liang, T.; Neumann, C.; Ritter, T.
Angew. Chem., Int. Ed. 2013, 52, 8214. (b) Mu, X.; Liu, G. Org. Chem.
Front. 2014, 1, 430. (c) Ma, J.; Li, S. Org. Chem. Front. 2014, 1, 712.
(
(
d) Cresswell, A. J.; Davies, S. G.; Roberts, P. M.; Thomson, J. E. Chem.
Rev. 2015, 115, 566. (e) Campbell, M. G.; Ritter, T. Chem. Rev. 2015,
15, 612. (f) O’Hagan, D.; Deng, H. Chem. Rev. 2015, 115, 634.
g) Charpentier, J.; Fruh, N.; Togni, A. Chem. Rev. 2015, 115, 650.
h) Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683. (i) Xu,
(
1
(
(
(
3
̈
X.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731. (j) Ni, C.; Hu,
M.; Hu, J. Chem. Rev. 2015, 115, 765. (k) Yang, X.; Wu, T.; Phipps, R. J.;
Toste, F. D. Chem. Rev. 2015, 115, 826.
(
2) For selected examples for synthesis of fluorinated arylhydrazones,
see: (a) Jiang, J.; Zhu, S. J. Fluorine Chem. 2008, 129, 40. (b) Li, F.; Sun,
C.; Wang, N. J. Org. Chem. 2014, 79, 8031. (c) Smirnov, V. O.;
Struchkova, M. I.; Arkhipov, D. E.; Korlyukov, A. A.; Dilman, A. D. J.
Org. Chem. 2014, 79, 11819. (d) Prieto, A.; Landart, M.; Baudoin, O.;
Monteiro, N.; Bouyssi, D. Adv. Synth. Catal. 2015, 357, 2939.
(
3) For selected reviews, see: (a) Hidai, M.; Mizobe, Y. Chem. Rev.
1995, 95, 1115. (b) Enders, D.; Wortmann, L.; Peters, R. Acc. Chem. Res.
2000, 33, 157. (c) Sugiura, M.; Kobayashi, S. Angew. Chem., Int. Ed.
2005, 44, 5176. (d) Lazny, R.; Nodzewska, A. Chem. Rev. 2010, 110,
1386. (e) Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev.
2011, 111, 2626.
(
4) (a) Fischer, E.; Jourdan, F. Ber. Dtsch. Chem. Ges. 1883, 16, 2241.
b) Fischer, E.; Hess, O. Ber. Dtsch. Chem. Ges. 1884, 17, 559. For
selected reviews, see: (c) Robinson, B. Chem. Rev. 1963, 63, 373.
d) Robinson, B. Chem. Rev. 1969, 69, 227. (e) Humphrey, G. R.;
Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
5) (a) Knolker, H. J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
b) Schmidt, A. W.; Reddy, K. R.; Knolker, H. J. Chem. Rev. 2012, 112,
193.
6) (a) Fustero, S.; Sanchez-Rosello, M.; Barrio, P.; Simon-Fuentes, A.
(
(
(
(
3
(
Chem. Rev. 2011, 111, 6984. For selected examples, see: (b) Surmont,
R.; Verniest, G.; De Kimpe, N. Org. Lett. 2010, 12, 4648. (c) Qian, J.; Liu,
Y.; Zhu, J.; Jiang, B.; Xu, Z. Org. Lett. 2011, 13, 4220. (d) Zhang, G.;
Zhao, Y.; Ge, H. Angew. Chem., Int. Ed. 2013, 52, 2559. (e) Vanjari, R.;
Guntreddi, T.; Kumar, S.; Singh, K. N. Chem. Commun. 2015, 51, 366.
D
Org. Lett. XXXX, XXX, XXX−XXX