3
900
Synthesis
M. Huang et al.
Paper
References
(11) (a) Mcloughlin, V. C. R.; Thrower, J. Tetrahedron 1969, 25, 5921.
(
(
b) Zhao, Y.; Hu, J. Angew. Chem. Int. Ed. 2012, 51, 1033.
c) Liang, A.; Li, X.; Liu, D.; Li, J.; Zou, D.; Wu, Y.; Wu, Y. Chem.
(
1) (a) Uneyama, K. Organofluorine Chemistry; Blackwell: Oxford,
006. (b) Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis,
Reactivity, Applications; Wiley-VCH: Weinheim, 2004.
c) Chambers, R. D. Fluorine in Organic Chemistry; Blackwell:
2
Commun. 2012, 48, 8273. (d) Xu, S.; Chen, H.-H.; Dai, J.-J.; Xu, H.-
J. Org Lett. 2014, 16, 2306. (e) Zhang, H.; Chen, P.; Liu, G. Angew.
Chem. Int. Ed. 2014, 53, 10174. (f) Song, W.; Lackner, S.;
Ackermann, L. Angew. Chem. Int. Ed. 2014, 53, 2477. (g) Fu, W.;
Zhou, M.; Xu, C.; Zhou, G.; Wang, Z.; Ji, B. J. Fluorine Chem. 2014,
(
Oxford, 2004. (d) Hiyama, T. Organofluorine Compounds: Chem-
istry, Applications; Springer: New York, 2000. (e) Ojima, I. Fluo-
rine in Medicinal Chemistry: Chemical Biology; Wiley: Chiches-
ter, 2009. (f) Bégué, J.-P.; Bonnet-Delphon, D. Bioorganic,
Medicinal Chemistry of Fluorine; Wiley: Hoboken, 2008.
168, 50. (h) Wu, G.; Deng, Y.; Wu, C.; Wang, X.; Zhang, Y.; Wang,
J. Eur. J. Org. Chem. 2014, 4477.
(
12) (a) Liu, C.-B.; Meng, W.; Li, F.; Wang, S.; Nie, J.; Ma, J.-A. Angew.
Chem. Int. Ed. 2012, 51, 6227. (b) Feng, Y.-S.; Xie, C.-Q.; Qiao, W.
L.; Xu, H. J. Org. Lett. 2013, 15, 936. (c) Hwang, J.; Park, K.; Choe,
J.; Min, K.; Song, K. H.; Lee, S. J. Org. Chem. 2014, 79, 3267.
(2) (a) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem.
Soc. Rev. 2008, 37, 320. (b) O’Hagan, D. Chem. Soc. Rev. 2008, 37,
3
1
08. (c) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317,
881. (d) Thayer, A. M. Chem. Eng. News 2006, 84,23 15.
(d) Han, E.-J.; Sun, Y.; Shen, Q.; Chen, Q.-Y.; Guo, Y.; Huang, Y.-G.
(
3) (a) Liu, X.; Xu, C.; Wang, M.; Liu, Q. Chem. Rev. 2015, 115, 683.
b) Xu, X. H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115,
Org. Chem. Front. 2015, 2, in press; DOI: 10.1039/C5QO00210A.
13) (a) Long, Z.-Y.; Chen, Q.-Y. Tetrahedron Lett. 1998, 39, 8487.
(
(
(
(
7
6
31. (c) Charpentier, J.; Früh, N.; Togni, A. Chem. Rev. 2015, 115,
50. (d) Ni, C.; Hu, M.; Hu, J. Chem. Rev. 2015, 115, 765.
(b) Long, Z.-Y.; Chen, Q.-Y. J. Org. Chem. 1999, 64, 4775.
14) Kreis, L. M. K.; Krautwald, S.; Pfeiffer, N.; Martin, R. E.; Carreira,
E. M. Org. Lett. 2013, 15, 1634.
(
e) Wang, S.-M.; Han, J.-B.; Zhang, C.-P.; Qin, H.-L.; Xiao, J.-C.
Tetrahedron 2015, 71, in press; doi: 10.1016/j.tet.2015.06.056.
f) Egami, H.; Sodeoka, M. Angew. Chem. Int. Ed. 2014, 53, 8294.
g) Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598.
15) (a) Fujiwara, Y.; Dixon, J. A.; O’Hara, F.; Funder, E. D.; Dixon, D.
D.; Rodriguez, R. A.; Baxter, R. D.; Herlé, B.; Sach, N.; Collins, M.
R.; Ishihara, Y.; Baran, P. S. Nature 2012, 492, 95. (b) Tang, X.-J.;
Thomoson, S. C.; Dolbier, W. R. Jr. Org. Lett. 2014, 16, 4594.
16) Fu, W.; Zhu, M.; Zou, G.; Xu, C.; Wang, Z. Synlett 2014, 25, 2513.
17) (a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev.
(
(
(
4) (a) Zhang, C.-P.; Chen, Q.-Y.; Guo, Y.; Xiao, J.-C.; Gu, Y.-C. Chem.
Soc. Rev. 2012, 41, 4536. (b) Zhang, C.-P.; Chen, Q.-Y.; Guo, Y.;
Xiao, J.-C. Tetrahedron 2013, 69, 10955. (c) Zhang, C.-P.; Chen,
Q.-Y.; Guo, Y.; Xiao, J.-C.; Gu, Y.-C. Coord. Chem. Rev. 2014, 261,
(
(
2013, 113, 5322. (b) Tucker, J. W.; Stephenson, C. R. J. J. Org.
28.
Chem. 2012, 77, 1617. (c) Lin, Q.-Y.; Xu, X.-H.; Qing, F.-L. Org.
Biomol. Chem. 2015, 13, 8740.
(
(
(
5) (a) Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1. (b) Nie, J.;
Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.
6) Nenajdenko, V. G.; Muzalevskiy, V. M.; Shastin, A. V. Chem. Rev.
(
18) (a) Tang, X. J.; Chen, Q.-Y. Org. Lett. 2012, 14, 6214. (b) Li, L.;
Chen, Q.-Y.; Guo, Y. J. Fluorine Chem. 2014, 167, 79. (c) Wang, Q.;
Huan, F.; Shen, H.; Xiao, J.-C.; Gao, M.; Yang, X.; Murahashi, S.-I.;
Chen, Q.-Y.; Guo, Y. J. Org. Chem. 2013, 78, 12525. (d) Li, L.;
Chen, Q.-Y.; Guo, Y. Chem. Commun. 2013, 49, 8764. (e) Wang,
W.; Huan, F.; Sun, Y.; Fang, J.; Liu, X.-Y.; Chen, Q.-Y.; Guo, Y.
J. Fluorine Chem. 2015, 171, 46. (f) Li, L.; Huang, D.; Chen, Q. Y.;
Guo, Y. Synlett 2013, 24, 611.
2
015, 115, 973.
7) (a) Chen, Q.-Y.; Wu, S.-W. J. Chem. Soc., Chem. Commun. 1989,
05. (b) Zhao, T. S. N.; Szabó, K. J. Org. Lett. 2012, 14, 3966.
c) Bouillon, J.-P.; Maliverney, C.; Merényi, R.; Viehe, H. G.
7
(
J. Chem. Soc., Perkin Trans.1 1991, 2147. (d) Miyake, Y.; Ota, S.;
Shibata, M.; Nakajima, K.; Nishibayashi, Y. Chem. Commun.
2013, 49, 7809.
(
(
(
19) (a) Lerch, M. M.; Morandi, B.; Wickens, Z. K.; Grubbs, R. H.
Angew. Chem. Int. Ed. 2014, 53, 8654. (b) Okusu, S.; Sugita, Y.;
Tokunaga, E.; Shibata, N. Beilstein J. Org. Chem. 2013, 9, 2189.
(8) Kawai, H.; Furukawa, T.; Nomura, Y.; Tokunaga, E.; Shibata, N.
Org. Lett. 2011, 13, 3596.
(9) (a) Parsons, A. T.; Buchwald, S. L. Angew. Chem. Int. Ed. 2011, 50,
(
c) Yang, T.-P.; Li, Q.; Lin, J.-H.; Xiao, J.-C. Chem. Commun. 2014,
0, 1077.
20) (a) Li, L.; Chen, Q.-Y.; Guo, Y. Chem. Commun. 2013, 49, 8764.
b) Zhang, K.; Liu, J-B.; Qing, F.-L. Chem. Commun. 2014, 50,
4157. (c) Xu, J.; Fu, Y.; Luo, D.-F.; Jiang, Y.-Y.; Xiao, B.; Liu, Z.-J.;
9120. (b) Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.;
5
Wang, J. J. Am. Chem. Soc. 2011, 133, 16410. (c) Xu, J.; Fu, Y.; Luo,
D.-F.; Jiang, Y.-Y.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Liu, L. J. Am.
Chem. Soc. 2011, 133, 15300. (d) Mizuta, S.; Galicia-López, O.;
Engle, K. M.; Verhoog, S.; Wheelhouse, K.; Rassias, G.;
Gouverneur, V. Chem. Eur. J. 2012, 18, 8583. (e) Shimizu, R.;
Egami, H.; Hamashima, Y. Angew. Chem. Int. Ed. 2012, 51, 4577.
(
1
Guo, T.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 15300. (d) Li, Q.-J.;
Ma, C.; Li, Q.-Z.; Du, W.; Chen, Y.-C. Org. Lett. 2014, 16, 3986.
21) (a) Li, L.; Chen, Q.-Y.; Guo, Y. J. Org. Chem. 2014, 79, 5145.
(f) Mizuta, S.; Engle, K. M.; Verhoog, S.; Galicia-López, O.;
(b) Guo, Y.; Tao, G. H.; Blumenfeld, A.; Shreeve, J. M. Organome-
O’Duill, M.; Médebielle, M.; Wheelhouse, K.; Rassias, G.;
Thompson, A. L.; Gouverneur, V. Org. Lett. 2013, 15, 1250.
tallics 2010, 29, 1818. (c) Guo, Y.; Twamley, B.; Shreeve, J. M.
Org. Biomol. Chem. 2009, 7, 1716.
(10) Chu, L.; Qing, F.-L. Org. Lett. 2012, 14, 2106.
©
Georg Thieme Verlag Stuttgart · New York — Synthesis 2015, 47, 3891–3900