Recent Progress in the Synthesis of Aryl Trifluoromethyl Ketones

doi:10.6023/cjoc201808046

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 74-83.DOI: 10.6023/cjoc201808046 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞

Reviews

芳基三氟甲基酮类化合物的合成进展

张洁雨, 柯求敏, 陈家英, 何平, 严国兵

丽水学院化学系丽水 323000

收稿日期:2018-08-31 修回日期:2018-10-16 发布日期:2018-10-26
通讯作者: 严国兵 E-mail:gbyan@lsu.edu.cn
基金资助:
浙江省自然科学基金（No.LY18B020005）资助项目.

Recent Progress in the Synthesis of Aryl Trifluoromethyl Ketones

Zhang Jieyu, Ke Qiumin, Chen Jiaying, He Ping, Yan Guobing

Department of Chemistry, Lishui University, Lishui 323000

Received:2018-08-31 Revised:2018-10-16 Published:2018-10-26
Contact: 10.6023/cjoc201808046 E-mail:gbyan@lsu.edu.cn
Supported by:
Project supported by the Natural Science Foundation of Zhejiang Province (No. LY18B020005).

Aryl trifluoromethyl ketone is a very important intermediate in the organic synthesis. Much attention has been attracted from researchers, due to its potential bioactivity. In this paper, the recent progress in the synthesis of aryl trifluoromethyl ketone is reviewed, including the oxidant of α-trifluoromethyl alcohols, trifluoromethylation of carboxylic acid derivatives, trifluoroacetylation of organometallic reagents, electron-rich aromatics, aryl halides and aryl diazonium salts, and the reaction mechanisms are also discussed.

Key words: aryl trifluoromethyl ketones, trifluoroacetylation, coupling reaction, reaction mechanism

Cite this article

Zhang Jieyu, Ke Qiumin, Chen Jiaying, He Ping, Yan Guobing. Recent Progress in the Synthesis of Aryl Trifluoromethyl Ketones[J]. Chin. J. Org. Chem., 2019, 39(1): 74-83.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Prakash, S, G.; Hu, J, B.; Alauddin, M, M.; Conti, P, S.; Olah, G, A. J. Fluorine Chem. 2003, 121, 239.
[2] Wang, J. J.; Li, F.; Xu, Y.; Wang, J.; Wu, Z. Y.; Yang, C. Y.; Liu, L. T. Chin. J. Org. Chem. 2018, 38, 1155.
[3] Zeng, Y. W.; Ni, C. F.; Hu, J. B. Chem.-Eur. J. 2016, 22, 3210.
[4] Kelly, C. B.; Mercadante, M. A.; Leadbeater, N. E. Chem. Commun. 2013, 49, 11133.
[5] Wu, W.; Weng, Z. Q. Synthesis 2018, 50, 1958.
[6] Gassman, P. G.; O'Reilly, N. J. J. Org. Chem. 1987, 52, 2481.
[7] Prakash, G. K. S.; Yudin, A. K. Chem. Rev. 1997, 97, 757.
[8] Linderman, R. J.; Graves, D. M. Tetrahedron Lett. 1987, 28, 4259.
[9] Linderman, R. J.; Graves, D. M. J. Org. Chem. 1989, 54, 661.
[10] Stavber, S.; KoŠir, I.; Zupan, M. J. Org. Chem. 1997, 62, 4916.
[11] Kelly, C. B.; Mercadante, M. A.; Hamlin, T. A.; Fletcher, M. H.; Leadbeater, N. E. J. Org. Chem. 2012, 77, 8131.
[12] Cheng, H.; Pei, Y.; Leng, F.; Li, J.; Liang, A.; Zou, D.; Wu, Y.; Wu, Y. Tetrahedron Lett. 2013, 54, 4483.
[13] Tanaka, Y.; Ishihara, T.; Konno, T. J. Fluorine Chem. 2012, 137, 99.
[14] Matano, Y.; Hisanaga, T.; Yamada, H.; Kusakabe, S.; Nomura, H.; Imahori, H. J. Org. Chem. 2004, 69, 8676.
[15] Matano, Y.; Suzuki, T.; Iwata, T.; Shinokura, T.; Imahori, H. Bull. Chem. Soc. Jpn. 2008, 81, 1621.
[16] Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. Science 1996, 274, 2044.
[17] Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Gautier, A.; Brown, S. M.; Urch, C. J. J. Org. Chem. 1999, 64, 2433.
[18] Kesavan, V.; Bonnet-Delpon, D.; Bégué, J.-P.; Srikanth, A.; Chandrasekaran, S. Tetrahedron Lett. 2000, 41, 3327.
[19] Blay, G.; Fernández, I.; Marco-Aleixandre, A.; Monje, B.; Pedro, J. R.; Ruiz, R. Tetrahedron 2002, 58, 8565.
[20] Mitchell, L.; Williamson, P.; Ehrlichová, B.; Anderson, A. E.; Seymour, V. R.; Ashbrook, S. E.; Acerbi, N.; Daniels, L. M.; Walton, R. I.; Clarke, M. L.; Wright, P. A. Chem. Eur. J. 2014, 20, 17185.
[21] Mei, Z.-W.; Omote, T.; Mansour, M.; Kawafuchi, H.; Takaguchi, Y.; Jutand, A.; Tsuboi, S.; Inokuchi, T. Tetrahedron 2008, 64, 10761.
[22] Kadoh, Y.; Tashiro, M.; Oisaki, K.; Kanai, M. Adv. Synth. Catal. 2015, 357, 2193.
[23] Kobayashi, Y.; Yamamoto, K.; Kumadaki, I. Tetrahedron Lett. 1979, 20, 4071.
[24] Krishnamurti, R.; Bellew, D. R.; Prakash, G. K. S. J. Org. Chem. 1991, 56, 984.
[25] Naumann, D.; Finke, M.; Lange, H.; Dukat, W.; Tyrra, W. J. Fluorine Chem. 1992, 56, 215.
[26] Kremlev, M. M.; Mushta, A. I.; Tyrra, W.; Naumann, D.; Fischer, H. T. M.; Yagupolskii, Y. L. J. Fluorine Chem. 2007, 128, 1385.
[27] Chang, Y.; Cai, C. J. Fluorine Chem. 2005, 126, 937.
[28] Yokoyama, Y.; Mochida, K. Synlett 1997, 907.
[29] Wiedemann, J.; Heiner, T.; Mloston, G.; Prakash, G. K. S.; Olah, G. A. Angew. Chem., Int. Ed. 1998, 37, 820.
[30] Singh, R. P.; Cao, G.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2873.
[31] Kawano, Y.; Kaneko, N.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2006, 79, 1133.
[32] Prakash, G. K. S.; Jog, P. V.; Batamack, P. T. D.; Olah, G. A. Science 2012, 338, 1324.
[33] Rudzinski, D. M.; Kelly, C. B.; Leadbeater, N. E. Chem. Commun. 2012, 48, 9610.
[34] Shidlovskii, A. F.; Golubev, A. S.; Gusev, D. V.; Suponitsky, K. Y.; Peregudov, A. S.; Chkanikov, N. D. J. Fluorine Chem. 2012, 143, 272.
[35] Allendörfer, N.; Es-Sayed, M.; Nieger, M.; Bräse, S. Tetrahedron Lett. 2012, 53, 388.
[36] McGrath, T. F.; Levine, R. J. Am. Chem. Soc. 1955, 77, 3656.
[37] Chen, L. S.; Chen, G. J.; Tamborski, C. J. Fluorine Chem. 1981, 18, 117.
[38] Chen, L. S.; Chen, G. J.; Tamborski, C. J. Organomet. Chem. 1983, 251, 139.
[39] Creary, X. J. Org. Chem. 1987, 52, 5026.
[40] Kerdesky, F. A. J.; Basha, A. Tetrahedron Lett. 1991, 32, 2003.
[41] Yamazaki, T.; Terajima, T.; Kawasaki-Taskasuka, T. Tetrahedron 2008, 64, 2419.
[42] Funabiki, K.; Hayakawa, A.; Inuzuka, T. Org. Biomol. Chem. 2018, 16, 913.
[43] Simchen, G.; Schmidt, A. Synthesis 1996, 1093.
[44] Wynne, J. H.; Lloyd, C. T.; Jensen, S. D.; Boson, S.; Stalick, W. M. Synthesis 2004, 2277.
[45] Wang, S.; Nie, J.; Zheng, Y.; Ma, J.-A. Org. Lett. 2014, 16, 1606.
[46] Yao, S.-J.; Ren, Z.-H.; Wang, Y.-Y.; Guan, Z.-H. J. Org. Chem. 2016, 81, 4226.
[47] Vitaku, E.; Smith, D. T.; Njardarson, J. T. Angew. Chem., Int. Ed. 2016, 55, 2243.
[48] Kakino, R.; Shimizu, I.; Yamamoto, A. Bull. Chem. Soc. Jpn. 2001, 74, 371.
[49] Zhu, F.; Yang, G.; Zhou, S.; Wu, X.-F. RSC Adv. 2016, 6, 57070.
[50] Wu, W.; Tian, Q.; Chen, T.; Weng, Z. Chem.-Eur. J. 2016, 22, 16455.
[51] Yan, G.; Cao, X.; Zheng, W.; Ke, Q.; Zhang, J.; Huang, D. Org. Biomol. Chem. 2017, 15, 5904.

芳基三氟甲基酮类化合物的合成进展

Recent Progress in the Synthesis of Aryl Trifluoromethyl Ketones

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Wenwen Chen, Qin Zhang, Songyue Zhang, Fangfang Huang, Xinyin Zhang, Jianfeng Jia. Visible Light Promoted Coupling Reaction of Alkynyl Iodide and Sodium Sulphinate without Photocatalyst [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 584-592.
[2]	Zujia Chen, Shiwei Yu, Yongjun Zhou, Huanqing Li, Qiwen Qiu, Miaoxin Li, Zhaoyang Wang. Application of BF₃•OEt₂ in Organic Synthesis as a Catalyst or Synthon [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3107-3118.
[3]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[4]	Cunjing Miao, Jiaqi Yao. Recent Advances in the Transformation Reactions of Aromatic Nitriles via C—CN Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1341-1364.
[5]	Ning Liu, Xiaodan Cuan, Hui Li, Xiyan Duan. Progress in the Study of α-Functionalization of Enaminone [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 602-621.
[6]	Menghan Shen, Laiqiang Li, Quan Zhou, Jiehui Wang, Lei Wang. Visible-Light-Induced Regio-selective Oxidative Coupling of Quinoxalinones with Pyrrole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 697-704.
[7]	Yueling Liu, Xinxin Zhong, Ganbing Zhang. Density Functional Theory Study for Exploring the Mechanisms of the [3＋2] Cycloaddition Reactions between 1-R-3-Phenylpropylidenecyclopropane (R=Me/H) and Furfural Catalyzed by Pd(0) [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 660-667.
[8]	Biao Ma, Miaomiao Zhang, Zhanyu Li, Jinsong Peng, Chunxia Chen. Recent Advance of Transition Metal-Free Catalyzed Suzuki-Type Cross Coupling Reaction [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 455-470.
[9]	Tingting Liu, Yucai Hu, An Shen. Mechanism of Carbon-Carbon Coupling Reactions Catalyzed by Imine-Ligand-Assisted N-Heterocyclic Carbene Palladium Complexes [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 622-628.
[10]	Sining Qin. Research Progress in C—S Coupling Reactions of Aryl Halides [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3761-3783.
[11]	Wei-Yuan Ma, Huifang Dai, Shaolin Kang, Tianlin Zhang, Xing-Zhong Shu. Hiyama Cross-Coupling Reaction of Aryl Vinylsilanes and Aryl Halides [J]. Chinese Journal of Organic Chemistry, 2023, 43(10): 3614-3622.
[12]	Jing Wang, Linlin Wu, Qian Wang. Synthesis and Characterization of New Indeno[1,2-b]fluorene-6,12-dione Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 223-228.
[13]	Geyang Song, Dong Xue. Research Progress on Light-Promoted Transition Metal-Catalyzed C-Heteroatom Bond Coupling Reactions [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2275-2299.
[14]	Rui Bai, Xujuan Liu, Wenyu Luo, Shanshan Liu, Linyu Jiao. Research Progress of Chan-Lam Coupling Reaction in Heterogeneous Catalysis [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2342-2354.
[15]	Lizhi Zhang, Yongjian Liao, Ning Chen, Lei Huang, Min Zhou. Cyclization and Coupling Reactions Promoted by Potassium tert-Butoxide [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1950-1959.