Organic Letters
Letter
Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236. (e) Liu, Z.; Wang, J. J.
Org. Chem. 2013, 78, 10024. (f) Xia, Y.; Zhang, Y.; Wang, J. ACS Catal.
2013, 3, 2586.
AUTHOR INFORMATION
Corresponding Author
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Notes
(14) Wang, X.; Xu, Y.; Deng, Y.; Zhou, Y.; Feng, J.; Ji, G.; Zhang, Y.;
Wang, J. Chem.Eur. J. 2014, 20, 961.
́ ́
(15) Jimenez-Aquino, A.; Vega, J. A.; Trabanco, A. A.; Valdes, C. Adv.
The authors declare no competing financial interest.
Synth. Catal. 2014, 356, 1079.
(16) Hu, M.; He, Z.; Gao, B.; Li, L.; Ni, H.; Hu, J. J. Am. Chem. Soc.
2013, 135, 17302.
ACKNOWLEDGMENTS
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(17) (a) Sakoda, K.; Mihara, J.; Ichikawa, J. Chem. Commun. 2005,
4684. (b) Ichikawa, J.; Sakoda, K.; Mihara, J.; Ito, N. J. Fluorine Chem.
2006, 127, 489. (c) Ichikawa, J.; Nadano, R.; Ito, N. Chem. Commun.
2006, 4425. (d) Ichitsuka, T.; Fujita, T.; Arita, T.; Ichikawa, J. Angew.
Chem., Int. Ed. 2014, 53, 7564.
This project was supported by the 973 program
(2012CB821600) and NSFC (Grant Nos. 21472004 and
21332002).
REFERENCES
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(18) Ye, F.; Ma, X.; Xiao, Q.; Li, H.; Zhang, Y.; Wang, J. J. Am. Chem.
Soc. 2012, 134, 5742.
(1) For 1,3-enynes in natural products, see: (a) Tsukamoto, S.;
Takahashi, M.; Matsunaga, S.; Fusetani, N.; Van Soest, R. W. M. J. Nat.
Prod. 2000, 63, 682. (b) Autunes, L. M.; Organ, M. G. Tetrahedron Lett.
2003, 44, 6805. In organic synthesis, see: (c) Nicolaou, K. C.; Dai, W.
M.; Tsay, S. C.; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172.
(d) Trost, B. M. Angew. Chem., Int. Ed. 1995, 34, 259. (e) Nicolaou, K.
C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F.,
Eds.; VCH: Weinheim, 1995. (f) Saito, S.; Yamamoto, Y. Chem. Rev.
2000, 100, 2901. In medicinal chemistry, see: (g) Zein, N.; Sinha, A. M.;
McGahren, W. J.; Ellestad, G. A. Science 1988, 240, 1198.
(h) Nussbaumer, P.; Leitner, L.; Marz, K.; Stutz, A. J. Med. Chem.
1995, 38, 1831. In material sciences, see: (i) Liu, Y.; Nishiura, M.; Wang,
Y.; Hou, Z. J. Am. Chem. Soc. 2006, 128, 5592. (j) Kaminker, R.; Biro, R.
P.; Boom, M. E. Angew. Chem., Int. Ed. 2011, 50, 3224.
(19) For Rh(I)-catalyzed cross-coupling reaction of diazo compounds
with arylboronic acids, see: (a) Ghorai, J.; Anbarasan, P. J. Org. Chem.
2015, 80, 3455. (b) Tsoi, Y.-T.; Zhou, Z.; Yu, W.-Y. Org. Lett. 2011, 13,
5370. For a Rh(III)-catalyzed reaction, see: (c) Ng, F.-N.; Lau, Y.-F.;
Zhou, Z.; Yu, W.-Y. Org. Lett. 2015, 17, 1676.
(20) For the proposed reaction mechanism, see the Supporting
Information. For a related report, see: Miura, T.; Ito, Y.; Murakami, M.
Chem. Lett. 2008, 37, 1006.
(2) For selected recent reviews on organofluorine chemistry, see:
(a) Kirsch, P. Modern Fluoroorganic Chemistry: Synthesis, Reactivity,
Applications; Wiley-VCH: Weinheim, 2004. (b) Gladysz, J. A.; Curran,
D. P.; Horvat
Weinheim, 2005. (c) Horvat
Berlin, 2011. (d) Muller, K.; Faeh, C.; Diederich, F. Science 2007, 317,
́
h, I. T. Handbook of Fluorous Chemistry; Wiley-VCH:
́
h, I. T. Fluorous Chemistry; Springer-Verlag:
̈
1881. (e) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.
(3) (a) Umemoto, T. In Fluorine-Containing Synthons; Soloshonok, V.
A., Ed.; American Chemical Society: Washington, DC, 2005. (b) Hu, J.;
Zhang, W.; Wang, F. Chem. Commun. 2009, 7465. (c) Cahard, D.; Xu,
X.; Couve-Bonnaire, S.; Pannecoucke, X. Chem. Soc. Rev. 2010, 39, 558.
(d) Ma, J.-A.; Cahard, D. Chem. Rev. 2004, 104, 6119. (e) Ma, J.-A.;
Cahard, D. Chem. Rev. 2008, 108, PR1−PR43. (f) Nie, J.; Guo, H.-C.;
Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455. (g) Wang, J.; Liu, H.
Chin. J. Org. Chem. 2011, 31, 1785.
(4) Silveira, C. C.; Braga, A. L.; Vieira, A. S.; Zeni, G. J. Org. Chem.
2003, 68, 662 and references cited therein.
(5) (a) Xu, Z.-Q.; Zamlicka, J. Tetrahedron 1997, 53, 5389. (b) Eddarir,
S.; Francesch, C.; Mestdagh, H.; Rolando, C. Bull. Soc. Chim. Fr. 1997,
134, 741. (c) Saito, S.; Kawasaki, T.; Tsuboya, N.; Yamamoto, Y. J. Org.
Chem. 2001, 66, 796. (d) Wang, Y.; Xu, J.; Burton, D. J. J. Org. Chem.
2006, 71, 7780. (e) Kumar, R.; Zajc, B. J. Org. Chem. 2012, 77, 8417.
(6) Burton, D. J.; Lee, T. M. J. Fluorine Chem. 1976, 8, 189.
(7) (a) Tellzer, F.; Sauvet
27, 3147. (b) Tellzer, F.; Sauvet
Chem. 1987, 328, 1.
̂
re, R.; Normant, J.-F. Tetrahedron Lett. 1986,
̂
re, R.; Normant, J.-F. J. Organomet.
(8) (a) Yang, Z.-Y.; Burton, D. J. Tetrahedron Lett. 1990, 31, 1369.
(b) Yang, Z.-Y.; Morken, P. A.; Burton, D. J. J. Fluorine Chem. 1991, 52,
443. (c) Crisp, G. T.; Robertson, T. A. Tetrahedron 1992, 48, 3239.
(d) Chen, S.; Xu, C.; Lv, L.; Shen, Q. Chin. J. Chem. 2013, 31, 901.
(9) Ichikawa, J.; Ikeura, C.; Minami, T. J. Fluorine Chem. 1993, 63, 281.
(10) Shen, Q.; Hammond, G. B. Org. Lett. 2001, 3, 2213.
(11) (a) Han, S. Y.; Choi, J. H.; Hwang, J. H.; Jeong, I. H. Bull. Korean
Chem. Soc. 2010, 31, 1121. (b) Jeon, J. H.; Kim, J. H.; Jeong, Y. J.; Jeong,
I. H. Tetrahedron Lett. 2014, 55, 1292. (c) Kim, J. H.; Jeong, Y. R.; Jeon,
S. L.; Jeong, I. H. J. Fluorine Chem. 2014, 167, 166.
(12) Saito, S.; Tanaka, T.; Koizumi, T.; Tsuboya, N.; Itagaki, H.;
Kawasaki, T.; Endo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 1810.
(13) For reviews, see: (a) Zhang, Y.; Wang, J. Eur. J. Org. Chem. 2011,
1015. (b) Barluenga, J.; Valdes
(c) Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560. (d) Xiao, Q.;
́
, C. Angew. Chem., Int. Ed. 2011, 50, 7486.
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