Copper-Catalyzed Trifluoromethylation of Enol Ether

doi:10.6023/cjoc201403039

Cite this article

Peng Rui, Yang Binmiao, Chen Zhimin, Xu Li, Wang Shaohua. Copper-Catalyzed Trifluoromethylation of Enol Ether[J]. Chin. J. Org. Chem., 2014, 34(5): 980-984.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

[1] (a) Uneyama, K. Organofluorine Chemistry, Blackwell, Oxford, U. K., 2006.

(b) Hird, M. Chem. Soc. Rev. 2007, 36, 2070.

(c) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.

(d) O’Hagan, D. Chem. Soc. Rev. 2008, 37, 308.

(e) Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell, Chichester, U. K., 2009.

(f) Filler, R; Saha, R. Future Med. Chem. 2009, 1, 777.

(g) Daniels, S.; Tohid, S. F. M.; Velanguparackel, W.; Westwell, A. D. Expert. Opin. Drug Discovery 2010, 5, 291.

(h) Acena, J. L.; Simon-Fuentes, A.; Fustero, S. Curr. Org. Chem. 2010, 14, 928.

(i) Wang, X.; Zhang, Y.; Wang, J. Sci. China Chem. 2012, 42, 1417 (in Chinese).

(王兮, 张艳, 王剑波, 中国科学: 化学, 2012, 42, 1417.)

(j) Qing, F. L. Chin. J. Org. Chem. 2012, 32, 815 (in Chinese).

(卿凤翎, 有机化学, 2012, 32, 815.)

(k) Lv, C. P.; Shen, Q. L.; Liu, D. Chin. J. Org. Chem. 2012, 32, 1380 (in Chinese).

(吕翠萍, 沈其龙, 刘丹, 有机化学, 2012, 32, 1380.)

(l) Pan, F.; Shi, Z. Acta Chim. Sinica 2012, 70, 1679 (in Chinese).

(潘菲, 施章杰, 化学学报, 2012, 70, 1679.)

(m) Yu, H. Z.; Su, S. Q.; Zhang, C.; Dang, Z. M. Chin. J. Org. Chem. 2013, 33, 1628 (in Chinese).

(于海珠, 苏圣钦, 张弛, 党智敏, 有机化学, 2013, 33, 1628.)

(n) Liu, T. F; Shen, Q, L. Eur. J. Org. Chem. 2012, 6679.

(o) Wang, G. Z.; He, X. P.; Dai, J. J.; Xu, H. J. Chin. J. Org. Chem. 2014, 34, 837 (in Chinese).

(王光祖, 赫侠平, 戴建军, 许华建, 有机化学, 2014, 34, 837.)

[2] (a) Swarts, F. Bull. Acad. R. Belg. 1892, 24, 309.

(b) Boswell, G. A., Jr.; Ripka, W. C.; Scribner, R. M.; Tullock, C. W. Org. React. 1974, 21, 1.

[3] (a) Dubinina, G. G.; Brennessel, W. W.; Miller, J. L.; Vicic, D. A. Organometallics 2008, 27, 3933.

(b) Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648.

(c) Ye, Y.; Ball, N. D.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2010, 132, 14682.

(d) Ye, Y.; Lee, S. H.; San ford, M. S. Org. Lett. 2011, 13, 5464.

(e) Parsons, A. T.; Senecal, T. D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2012, 51, 2947.

(f) Herrmann, A. T.; Smith, L. L.; Zakarian, A. J. Am. Chem. Soc. 2012, 134, 6976.

(g) Iqbal, N.; Choi, S.; Kim, E.; Cho, E. J. J. Org. Chem. 2012, 77, 11383.

(h) Kazuyuki, S.; Masaaki, O.; Akira, A.; Itsumaro, K. Org. Lett. 2013, 23, 4359.

[4] (a) Zhang, S.-L.; Liu, L.; Fu, Y.; Guo, Q.-X. Organometallics 2007, 26, 4546.

(b) Dubinina, G. G.; Furutachi, H.; Vicic, D. A. J. Am. Chem. Soc. 2008, 130, 8600.

(c) Oishi, M.; Kondo, H.; Amii, H. Chem. Commun. 2009, 1909.

(d) Morimoto, H.; Tsubogo, T.; Litvinas, N. D.; Hartwig, J. F. Angew. Chem., Int. Ed. 2011, 50, 3793.

(e) Zanardi, A.; Novikov, M. A.; Martin, E.; Benet-Buchholz, J.; Grushin, V. V. J. Am. Chem. Soc. 2011, 133, 20901.

(f) Tomashenko, O. A.; Escudero-Adan, E. C.; Belmonte, M. M.; Grushin, V. V. Angew. Chem., Int. Ed. 2011, 50, 7655.

(g) Zhang, C. P.; Wang, Z. L.; Chen, Q. Y.; Zhang, C. T.; Gu, Y. C.; Xiao, J. C. Angew. Chem., Int. Ed. 2011, 50, 1896.

(h) Weng, Z.; Lee, R.; Jia, W.; Yuan, Y.; Wang, W.; Feng, X.; Huang, K. W. Organometallics 2011, 30, 3229.

(i) Kondo, H.; Oishi, M.; Fujikawa, K.; Amii, H. Adv. Synth. Catal. 2011, 353, 1247.

(j) Knauber, T.; Arikan, F.; Roschenthaler, G.-V.; Goossen, L. J. Chem. Eur. J. 2011, 17, 2689.

(k) Duan, C.; Li, Y.; Chen, T.; Wang, H.; Zhang, R.; Jin, K.; Wang, X. Synlett 2011, 1713.

(l) Chen, M.; Buchwald, S. L. Angew. Chem., Int. Ed. 2013, 52, 11628.

(m) Hafner, A.; Braese, S. Adv. Synth. Catal. 2011, 353, 3044.

(n) Kawai, H.; Furukawa, T.; Nomura, Y.; Tokunaga, E.; Shibata, N. Org. Lett. 2011, 13, 3596.

(o) Schareina, T.; Wu, X.-F.; Zapf, A.; Cotté, A.; Gotta, M.; Beller, M. Top. Catal. 2012, 55, 426.

(p) Miyake, Y.; Ota, S.; Nishibayashi, Y. Chem.-Eur. J. 2012, 18, 13255.

(q) Zhao, T. S.; Szabo, K. J. Org. Lett. 2012, 14, 3966.

(r) Novak, P.; Lishchynskyi, A.; Grushin, V. V. J. Am. Chem. Soc. 2012, 134, 16167.

(s) Miyake, Y.; Ota, S.; Shibata, M.; Nakajima, K.; Nishibayashi, Y. Chem. Commum. 2013, 49, 7809.

(t) Larsson, J. M.; Pathipati, S. R.; Szabo, K. J. J. Org. Chem. 2013, 78, 7330.

(u) Ambler, B. R.; Altman, R. A. Org. Lett. 2013, 15, 5578.

[5] (a) Chu, L.; Qing, F.-L. Org. Lett. 2010, 12, 5060.

(b) Senecal, T. D.; Parsons, A. T.; Buchwald, S. L. J. Org. Chem. 2011, 76, 1174.

(c) Xu, J.; Luo, D. F.; Xiao, B.; Liu, Z. J.; Gong, T. J.; Fu, Y.; Liu, L. Chem. Commun. 2011, 47, 4300.

(d) Zhang, C. P.; Cai, J.; Zhou, C. B.; Wang, X. P.; Zheng, X.; Gu, Y. C.; Xiao, J. C. Chem. Commun. 2011, 47, 9516.

(e) Liu, T.; Shen, Q. Org. Lett. 2011, 13, 2342.

(f) Huang, Y.; Fang, X.; Lin, X.; Li, H.; He, W.; Huang, K.-W.; Yuan, Y.; Weng, Z. Tetrahedron 2012, 68, 9949.

(g) Ji, Y.; Brueckl, T.; Baxter, R. D.; Fujiwara, Y.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 14411.

(h) Ye, Y.; Kü nzi, S. A.; Sanford, M. S. Org. Lett. 2012, 14, 4979.

(i) Litvinas, N. D.; Fier, P. S.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 536.

(j) Liu, T.; Shao, X.; Wu, Y.; Shen, Q. Angew. Chem., Int. Ed. 2012, 51, 555.

(k) Novák, P.; Lishchynskyi, A.; Grushin, V. V. Angew. Chem., Int. Ed. 2012, 51, 7767.

(l) Khan, B. A.; Buba, A. E.; Goossen, L. J. Chem.-Eur. J. 2012, 18, 1577.

(m) Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2012, 134, 9034.

(n) Xu, J.; Xiao, B.; Xie, C. Q.; Luo, D. F.; Liu, L.; Fu, Y. Angew. Chem., Int. Ed. 2012, 51, 12551.

(o) Zheng, H.; Huang, Y.; Wang, Z.; Li, H.; Huang, K.-W.; Yuan, Y.; Weng, Z. Tetrahedron Lett. 2012, 53, 6646.

(p) Li, Y.; Wu, L.; Neumann, H.; Beller, M. Chem. Commun. 2013, 49, 2628.

[6] (a) Chu, L.; Qing, F.-L. Org. Lett. 2010, 14, 2106.

(b) 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.

(c) Parsons, A. T.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 9120.

(d) Wang, X.; Ye, Y.; Zhang, S.; Feng, J.; Xu, Y.; Zhang, Y.; Wang, J. J. Am. Chem. Soc. 2011, 133, 16410.

(e) Mitsudera, H.; Li, C.-J. Tetrahedron Lett. 2011, 52, 1898.

[7] (a) Shimizu, R.; Egami, H.; Nagi, T.; Chae, J.; Hamashima, Y.; Sodeoka, M. Tetrahedron Lett. 2010, 51, 5947.

(b) Chu, L.; Qing, F. L. J. Am. Chem. Soc. 2012, 134, 1298.

(c) Pair, E.; Monteiro, N.; Bouyssi, D.; Baudoin, O. Angew. Chem., Int. Ed. 2013, 52, 5346.

(d) Feng, C.; Loh, T.-P. Chem. Sci. 2012, 3, 3458.

(e) Ilchenko, N. O.; Janson, P. G.; Szabo, K. J. Chem. Commun. 2013, 49, 6614.

(f) Wang, X.; Ye, Y.; Ji, G.; Xu, Y.; Zhang, S.; Feng, J.; Zhang, Y.; Wang, J. Org. Lett. 2013, 15, 3730.

[8] (a) Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2010, 132, 7262.

(b) Weng, Z.; Li, H.; He, W.; Yao, L.-F.; Tan, J.; Chen, J.; Yuan, Y.; Huang, K.-W. Tetrahedron 2012, 68, 2527.

(c) Luo, D.-F.; Xu, J.; Fu, Y.; Guo, Q.-X. Tetrahedron Lett. 2012, 53, 2769.

(d) Zhang, K.; Qiu, X.-L.; Huang, Y.; Qing, F.-L. Eur. J. Org. Chem. 2012, 58. (a) Chen, Z.-M.; Bai, W.; Wang, S.-H.; Yang, B.-M.; Tu, Y.-Q.; Zhang, F.-M. Angew. Chem., Int. Ed. 2013, 52, 9781.

(b) Fang, Z.; Ning, Y.; Mi, P.; Liao, P.; Bi, X., Org. Lett. 2014, 16, 1522.

[1]	Si Wen, Yuhao Ding, Qingyu Tian, Jin Ge, Guolin Cheng. Rhodium(III)-Catalyzed Synthesis of CF₃-1H-benzo[de][1,8]naph-thyridines via C—H Activation/Annulation of Benzimidates and CF₃-Imidoyl Sulfoxonium Ylides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 291-300.
[2]	Hu Ma, Danfeng Huang, Kehu Wang, Duoduo Tang, Yang Feng, Yuanyuan Reng, Junjiao Wang, Yulai Hu. Synthesis of 3-Trifluoromethylpyrazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3257-3267.
[3]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[4]	Xiao Song, Jing Qing, Jun Li, Xuelei Jia, Fusong Wu, Junrong Huang, Jian Jin, Hengzhi You. Copper-Catalyzed Asymmetric Allyl Alkylation Using Grignard Reagents under Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3174-3179.
[5]	Xiaoyu Lu, Xiaomei Sun, Yaqing Niu, Junchao Wang, Wenjing Yin, Mengting Gao, Zi Liu, Zhenghuan Wei, Tinghua Tao. Copper-Catalyzed Decarboxylative Cross-Coupling of α‑Fluoroacrylic Acids with N-Tosyl Oxaziridines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2110-2119.
[6]	Zhicheng Bao, Muyao Li, Jianbo Wang. Copper-Catalyzed Cross-Coupling of Aryldiazoacetates with Bis[(pinacolato)boryl]methane [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1808-1814.
[7]	Jing Liu, Jian Hao, Qilong Shen. Visible-Light-Promoted Direct Trifluoromethylation of Tryptophan-Containing Oligapeptides with YlideFluor [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1517-1524.
[8]	Chunsheng Li, Xiaoqi Lian, Lianfen Chen. Copper-Catalyzed [4＋2] Annulations of Sulfoxonium Ylides and o-Phenylenediamines [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1492-1498.
[9]	Yang Liu, Xiang Huang, Min Wang, Jian Liao. Enantioselective Copper-Catalyzed Mannich-Type Reaction of Cycic Ketimines and β,γ-Unsaturated N-Acylpyrazoles [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1499-1509.
[10]	Chunyang Liu, Yan Li, Qian Zhang. Copper-Catalyzed Allylic C(sp³)—H Sulfonylation of Cyclic Olefins [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1091-1101.
[11]	Rui Wang, Lang Gao, Cen Zhou, Xiao Zhang. Haloperfluoroalkylation of Unactivated Terminal Alkenes over Phenylphenothiazine-Based Porous Organic Polymers [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1136-1145.
[12]	Yasir Mumtaz, Jie Liu, Xin Huang. Copper-Promoted Trifluoromethylthiolation of Anilines with CF₃SO₂Na [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 679-685.
[13]	Biao Han, Weishuang Li, Shuhan Chen, Zelang Zhang, Xue Zhao, Yaoyao Zhang, Lei Zhu. Recent Advances in Copper-Catalyzed Silyl Addition of Unsaturated Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 555-572.
[14]	Shuyong Song, Senmiao Xu. Recent Progress in Selective C-F Bond Activation of Trifluoromethyl Alkenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 411-425.
[15]	Zhiyuan Chen, Mengwei Yang, Jianlin Xu, Yunhe Xu. Regioselective Synthesis of β-Silyl-Substituted Vinylphosphine Oxides via Copper-Catalyzed Protosilylation of Dialkynylphosphine Oxides [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3598-3607.

铜催化烯醚的三氟甲基化反应