Recent Advances in Catalytic Asymmetric Friedel-Crafts Reactions with Prochiral Trifluoromethylated Compounds

doi:10.6023/A13010078

Acta Chimica Sinica ›› 2013, Vol. 71 ›› Issue (05): 700-712.DOI: 10.6023/A13010078 Previous Articles Next Articles

Review

基于三氟甲基砌块的催化不对称傅-克反应研究进展

何展荣^a, 黄毅勇^b, Verpoort Francis^b,c

a 四川职业技术学院建筑与环境工程系遂宁 629000;
b 武汉理工大学理学院化学系武汉 430070;
c 武汉理工大学复合材料国家重点实验室武汉 430070

投稿日期:2013-01-16 发布日期:2013-03-05
通讯作者: 黄毅勇,huangyy@whut.edu.cn E-mail:huangyy@whut.edu.cn
基金资助:
项目受四川省教育厅科研项目基金(13ZA0034), 中央高校基本科研业务费专项资金(项目编号: 2013-IV-077), 湖北省“楚天学者计划”和中组部“外专千人计划”资助.

Recent Advances in Catalytic Asymmetric Friedel-Crafts Reactions with Prochiral Trifluoromethylated Compounds

He hanrong^a, Huang Yiyong^b, Verpoort Francis^b,c

a Department of Architecture and Environment Engineering, Sichuan Vocational and Technical College, Suining 629000;
b Department of Chemistry, School of Science, Wuhan University of Technology, Wuhan 430070;
c State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070

Received:2013-01-16 Published:2013-03-05
Supported by:
Project supported by the Sichuan Provincial Department of Education Scientific Research Fund Project (13ZA0034), the Fundamental Research Funds for the Central Universities (WUT: 2013-IV-077), the Chinese Hubei Government for a “Chutian Scholar” Honor, and the Chinese Central Government for an “Expert of the State” Position in the Program of “Thousand Talents”.

The incorporation of a trifluoromethyl (CF₃) group can increase chemical and metabolic stability, lipophilicity, and membrane permeability of the molecules. As a consequence, the exploitation of efficient methods to construct chiral trifluoromethylated compounds is a highly significant task. Two strategies are often utilized to synthesize compounds bearing a CF₃ group at the chiral center. The first strategy is the transfer of a CF₃ group from a reagent. This strategy seems to be straightforward and practical, but direct enantioselective trifluoromethylation remains a challenge, and high enantioselectivities are rarely reached. An alternative strategy is the application of some established asymmetric catalytic reactions by using trifluoromethylated compounds as building blocks, which could provide various chiral trifluoromethylated products in high yields and enantioselectivities under mild conditions. Asymmetric Friedel-Crafts reaction has witnessed rapid development in recent years. Asymmetric Friedel-Crafts reaction using prochiral trifluoromethylated starting materials represents an important method for the access of trifluoromethylated derivatives of chiral aromatic compounds. Since Mikami's group identified that chiral BINOL-derived Ti(IV) complexs could be applied in the asymmetric Friedel-Crafts reaction with fluoral to obtain chiral trifluoromethylated compounds, considerable efforts have been dedicated to utilize other chiral organometallic catalysts (such as chiral Ti, Cu, Zn, Zr, Pd, Y, Yb, Ni, Ca complex, etc.) and chiral organo-catalysts (such as cinchona alkaloids, chiral prolinol ethers, chiral phosphoric acids, etc.) in this type of catalytic reaction. Chiral trifluoromethylated compounds with a CF₃-group at a chiral carbon center with, or without any heteroatom substituents were obtained in high yields and enantioselectivities. The components (especially CF₃-containing starting material of trifluoromethyl ketones, imines and olefins), conditions and mechanism of the Friedel-Crafts reactions, and the synthetic utilities of Friedel-Crafts adducts are discussed in this review. Finally, the existing problem and limitation of this Friedel-Crafts reaction are summarized, and the key prospect of the chiral CF₃-containing product-driven Friedel-Crafts reaction is also described. The aim of this review is to stimulate further developments in this area.

Key words: asymmetric catalysis, Friedel-Crafts reaction, asymmetric synthesis, trifluoromethylated, chiral

Cite this article

He hanrong, Huang Yiyong, Verpoort Francis. Recent Advances in Catalytic Asymmetric Friedel-Crafts Reactions with Prochiral Trifluoromethylated Compounds[J]. Acta Chimica Sinica, 2013, 71(05): 700-712.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Chambers, R. D. Fluorine in Organic Chemistry, Blackwell, Oxford, 2004; (b) Shah, P.; Westwell, A. D. J. Enzyme Inhib. Med. Chem. 2007, 22, 527; (c) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881; (d) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305; (e) Lv, C.-P.; Shen, Q.-L.; Liu, D. Chin. J. Org. Chem. 2012, 32, 1380. (吕翠萍, 沈其龙, 刘丹, 有机化学, 2012, 32, 1380.); (f) Liu, J.-C.; Cui, Z.-P.; He, H.-W. Chin. J. Org. Chem. 2012, 32, 1925. (刘建超, 崔泽平, 贺红武, 有机化学, 2012, 32, 1925.); (g) Liang, Y.; He, H.-W.; He, H.-F.; Yang, Z.-W. Chin. J. Org. Chem. 2012, 32, 1513. (梁英, 贺红武, 何海峰, 杨自文, 有机化学, 2012, 32, 1513.)
[2] Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1.
[3] Qing, F.-L. Chin. J. Org. Chem. 2012, 32, 815. (卿凤翎, 有机化学, 2012, 32, 815).
[4] Tsutomu, K. Curr. Org. Syn. 2010, 7, 455.
[5] (a) Kawai, H.; Kusuda, A.; Nakamura, S.; Shiro, M.; Shibata, N. Angew. Chem. Int. Ed. 2009, 48, 6324; (b) Allen, A. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2010, 132, 4986; (c) Nagib, D. A.; Scott, M. E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2009, 131, 10875; (d) Deng, Q.-H.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2012, 134, 10769.
[6] Shibata, N.; Mizuta, S.; Kawai, H. Tetrahedron: Asymmetry 2008, 19, 2633.
[7] (a) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455; (b) Shibata, N.; Mizuta, S.; Kawai, H. Tetrahedron: Asymmetry 2008, 19, 2633.
[8] In Catalytic Asymmetric Friedel-Crafts Alkylations, Eds.: Bandini, M.; Umani-Ronchi, A., Wiley-VCH, Weinheim, 2009, pp. 1～301. For reviews: (a) Zeng, M.; You, S.-L. Synlett 2010, 1289; (b) Bandini, M.; Melloni, A.; Umani-Ronchi, A. Angew. Chem. Int. Ed. 2004, 43, 550; (c) Wang, Y.; Ding, K.-L. Chin. J. Org. Chem. 2001, 21, 763. (王以, 丁奎岭, 有机化学, 2001, 21, 763.)
[9] Erker, G.; van der Zeijden, A. A. H. Angew. Chem., Int. Ed. 1990, 29, 512.
[10] Ishii, A.; Mikami, K. J. Fluorine Chem. 1999, 97, 51.
[11] Ishii, A.; Soloslmtmk, V. A.; Mikami, K. J. Org. Chem. 2000, 65, 1597.
[12] Ishii, A.; Kojima, J. ; Mikami, K. Org. Lett. 1999, 1, 2013.
[13] Dong, H.-M.; Lu, H.-H.; Lu, L.-Q.; Chen, C.-B.; Xiao, W.-J. Adv. Synth. Catal. 2007, 349, 1597.
[14] Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903.
[15] Zhuang, W.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2001, 66, 1009.
[16] In Asymmetric Catalysis: New Concepts and Methods, Eds.: Ding, K.-L.; Fan, Q.-H. Chemical Industry Press, Beijing, 2008, pp. 1～656. (不对称催化新概念与新方法, 丁奎岭, 范青华主编, 化学工业出版社, 北京, 2008, pp. 1～656.)
[17] Corma, A.; García, H.; Moussaif, A.; Sabater, M. J.; Zniber, R.; Redouane, A. Chem. Commun. 2002, 1058.
[18] Lyle, M. P. A.; Draper, N. D.; Wilson, P. D. Org. Lett. 2005, 7, 901.
[19] Zhao, J.-L.; Liu, L.; Sui, Y.; Liu, Y.-L.; Wang, D.; Chen, Y.-J. Org. Lett. 2006, 8, 6127.
[20] Nakamura, S.; Hyodo, K.; Nakamura, Y.; Shibata, N.; Toru, T. Adv. Synth. Catal. 2008, 350, 1443.
[21] Wen, L.-L.; Shen, Q.-L.; Wan, X.-L.; Lu, L. J. Org. Chem. 2011, 76, 2282.
[22] Wolf, C.; Zhang, P. Adv. Synth. Catal. 2011, 353, 760.
[23] Selected examples of asymmetric Friedel-Crafts reaction of N-H pyrrole: (a) Trost, B. M.; Miller, C. J. Am. Chem. Soc. 2008, 130, 2438; (b) Evans, D. A.; Fandrick, K. R. Org. Lett. 2006, 8, 2249; (c) Li, G.-L.; Rowland, G. B.; Rowland, E. B.; Antilla, J. C. Org. Lett. 2007, 9, 4065; (d) Palomo, C.; Oiarbide, M.; Kardak, B. G.; Garcia, J. M.; Linden, A. J. Am. Chem. Soc. 2005, 127, 4154.
[24] (a) Huang, Y.-Y.; Tokunaga, E.; Suzuki, S.; Shiro, M.; Shibata, N. Org. Lett. 2010, 12, 1136; (b) Huang, Y.-Y.; Satoru, S.; Liu, G.-K.; Tokunaga, E.; Suzuki, S.; Shiro, M.; Shibata, N. New J. Chem. 2011, 35, 2614.
[25] Hui, Y.-H.; Chen, W.-L.; Wang, W.-T.; Jiang, J.; Cai, Y.-F.; Lin, L.-L.; Liu, X.-H.; Feng, X.-M. Adv. Synth. Catal. 2010, 352, 3174.
[26] Mikami, K.; Aikawa, K.; Kainuma, S.; Kawakami, Y.; Saito, T.; Sayob, N.; Kumobayashi, H. Tetrahedron: Asymmetry 2004, 15, 3885.
[27] Blay, G.; Fernández, I.; Monleón, A.; Pedro, J. R.; Vila, C. Org. Lett. 2009, 11, 441.
[28] Blay, G.; Fernández, I.; Mu?oz, M. C.; Pedro, J. R.; Vila, C. Chem. Eur. J. 2010, 16, 9117.
[29] Grach, G.; Dinut, A.; Marque, S.; Marrot, J.; Gil, R.; Prim, D. Org. Biomol. Chem. 2011, 9, 497.
[30] Wang, W.-T.; Lian, X.-J.; Chen, D.-H.; Liu, X.-H.; Lin, L.-L.; Feng, X.-M. Chem. Commun. 2011, 47, 7821.
[31] (a) Deng, Q.-H.; Wadepohl, H.; Gade, L. H. J. Am. Chem. Soc. 2012, 134, 10769; (b) Kawai, H.; Okusu, S.; Tokunaga, E.; Sato, H.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2012, 51, 4959.
[32] Gao, J.-R.; Wu, H.; Xiang, B.; Yu, W.-B.; Han, L.; Jia, Y.-X. J. Am. Chem. Soc. 2013, 135, 2983.
[33] (a) Harder, S. Chem. Rev. 2010, 110, 3852; (b) Kobayashi, S.; Yamashita, Y. Acc. Chem. Res. 2011, 44, 58.
[34] Rueping, M.; Bootwicha, T.; Kambutong, S.; Sugiono, E. Chem. Asian J. 2012, 7, 1195.
[35] For reviews: (a) Li, N.; Liu, W.-J.; Gong, L.-Z. Prog. Chem. 2010, 22, 1362. (李楠, 刘伟军, 龚流柱, 化学进展, 2010, 22, 1362.); (b) Sheng, Y.-F.; Zhang, A.-J.; Zheng, X.-J.; You, S.-L. Chin. J. Org. Chem. 2008, 28, 605. (盛益飞, 张安将, 郑晓建, 游书力, 有机化学, 2008, 28, 605.)
[36] Török, B.; Abid, M.; London, G.; Esquibel, J.; Török, M.; Mhadgut, S. C.; Yan, P.; Prakash, G. K. S. Angew. Chem., Int. Ed. 2005, 44, 3086.
[37] Zhao, J.-L.; Liu, L.; Gu, C.-L.; Wang, D.; Chen, Y.-J. Tetrahedron Lett. 2008, 49, 1476.
[38] Han, X.; Liu, B.; Zhou, H.-B.; Dong, C. Tetrahedron: Asymmetry 2012, 23, 1332.
[39] Paras, N. A.; MacMillan, D. W. C．J. Am. Chem. Soc. 2001, 123, 4370.
[40] Shibatomi, K.; Narayama, A.; Abe, Y.; Iwasa, S. Chem. Commun. 2012, 48, 7380.
[41] (a) Akiyama, T.; Itoh, J.; Yokota, K.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566; (b) Uragauchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356; (c) Akiyama, T. Chem. Rev. 2007, 107, 5744; (d) You, S.-L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 2190; (e) Terrasson, V.; de Figueiredo, R. M.; Campagne, J. M. Eur. J. Org. Chem. 2010, 2635.
[42] Zhang, G.-W.; Wang, L.; Nie, J.; Ma, J.-A. Adv. Synth. Catal. 2008, 350, 1457.
[43] Husmann, R.; Sugiono, E.; Mersmann, S.; Raabe, G.; Rueping, M.; Bolm, C. Org. Lett. 2011, 13, 1044.
[44] Nie, J.; Zhang, G.-W.; Wang, L.; Zheng, D.-H.; Zheng, Y.; Ma, J.-A. Eur. J. Org. Chem. 2009, 3145.
[45] Nie, J.; Zhang, G.-W.; Wang, L.; Fu, A.; Zheng, Y.; Ma, J.-A. Chem. Commun. 2009, 2356.
[46] Wang, T.; Zhang, G.-W.; Teng, Y.; Nie, J.; Zheng, Y.; Ma, J.-A. Adv. Synth. Catal. 2010, 352, 2773.
[47] Kashikura, W.; Itoh, J.; Mori, K.; Akiyama, T. Chem. Asian J. 2010, 5, 470.
[48] (a) Itoh, J.; Fuchibe, K.; Akiyama, T. Angew. Chem., Int. Ed. 2008, 47, 4016; (b) Sheng, Y.-F.; Li, G.-Q.; Kang, Q.; Zhang, A.-J.; You, S.-L. Chem. Eur. J. 2009, 15, 3351; (c) Sheng, Y.-F.; Gu, Q.; Zhang, A.-J.; You, S.-L. J. Org. Chem. 2009, 74, 6899.
[49] Lin, J.-H.; Xiao, J.-C. Eur. J. Org. Chem. 2011, 4536.
[50] Gong, Y.; Kato, K. Tetrahedron: Asymmetry 2001, 12, 2121.
[51] Abid, M.; Teixeira, L.; Török, B. Org. Lett. 2008, 10, 933.

基于三氟甲基砌块的催化不对称傅-克反应研究进展

Recent Advances in Catalytic Asymmetric Friedel-Crafts Reactions with Prochiral Trifluoromethylated Compounds

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Shan Li, Junxin Lu, Jie Liu, Lvqi Jiang, Wenbin Yi. Electrochemical Synthesis of α-Fluoroalkylated Ketones using Sodium Fluoroalkylsulfinate [J]. Acta Chimica Sinica, 2024, 82(2): 110-114.
[2]	Weiyang Gao, Weichao Deng, Yang Gao, Renxiao Liang, Yixia Jia. Intermolecular Enantioselective Dearomative Oxidative Heck Reaction of Indoles [J]. Acta Chimica Sinica, 2024, 82(1): 1-4.
[3]	Zhanglong Yu, Zhongliang Li, Changjiang Yang, Qiangshuai Gu, Xinyuan Liu. Research Progress on Copper-Catalyzed Enantioselective Desymmetrization of Diols^★ [J]. Acta Chimica Sinica, 2023, 81(8): 955-966.
[4]	Shuang Yang, Ningyi Wang, Qingqing Hang, Yuchen Zhang, Feng Shi. Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides^★ [J]. Acta Chimica Sinica, 2023, 81(7): 793-808.
[5]	Xinhong Cai, Jianzhong Chen, Wanbin Zhang. Development of Construction of Chiral C—X Bonds through Nickel Catalyzed Asymmetric Hydrogenation^★ [J]. Acta Chimica Sinica, 2023, 81(6): 646-656.
[6]	Wang Rui-Xiang, Zhao Qing-Ru, Gu Qing, You Shu-Li. Gold/Iridium Catalyzed Alkynylamide Cyclization/Asymmetric Allylic Benzylation Cascade Reaction^★ [J]. Acta Chimica Sinica, 2023, 81(5): 431-434.
[7]	Yang Gao, Xuexin Zhang, Jinsheng Yu, Jian Zhou. Recent Advances in Catalytic Enantioselective Synthesis of α-Chiral Tertiary Azides^★ [J]. Acta Chimica Sinica, 2023, 81(11): 1590-1608.
[8]	Yeqiang Han, Bingfeng Shi. Palladium(II)-Catalyzed Enantioselective Functionalization of C(sp³)—H Bonds^★ [J]. Acta Chimica Sinica, 2023, 81(11): 1522-1540.
[9]	Qingduan Meng, Jiahong Han, Yixiao Pan, Wei Hao, Qing-Hua Fan. Asymmetric Synthesis of C₁-Symmetric Chiral N-Heterocyclic Carbene (NHC) Ligands and Their Applications in Asymmetric Catalysis^★ [J]. Acta Chimica Sinica, 2023, 81(10): 1271-1279.
[10]	Xiaomao Tian, Yuequn Lin, Han Zhu, Chao Huang, Bixue Zhu. Enantiomers Identification of Penicillamine by Chiral Mono-Schiff Base Macrocycles [J]. Acta Chimica Sinica, 2023, 81(1): 20-28.
[11]	Lai Zhang, Jian Xiao, Yawen Wang, Yu Peng. Recent Advances on the Construction of Chiral Dihydrobenzofurans by Asymmetric [3+2] Cyclization Reactions of Phenols (Quinones) and Alkenes [J]. Acta Chimica Sinica, 2022, 80(8): 1152-1164.
[12]	Lixuan Liu, Yang Yang, Zhixiang Wei. Chiral Organic Optoelectronic Materials and Circularly Polarized Light Luminescence and Detection [J]. Acta Chimica Sinica, 2022, 80(7): 970-992.
[13]	Xicheng Feng, Liangliang Zhu, Bingbing Yue. Circularly Polarized Luminescence and Dynamic Regulation Based on the co-Assembly of L/D-Lysine Hydrochloride and Photoactivated AIE Molecules [J]. Acta Chimica Sinica, 2022, 80(5): 647-651.
[14]	Yiding Wang, Fuhai Li, Qingle Zeng. Advances in Formation of C—X Bonds via Cleavage of C—N Bond of Quaternary Ammonium Salts [J]. Acta Chimica Sinica, 2022, 80(3): 386-394.
[15]	Jinyue Ma, Lufei Huang, Baowen Zhou, Lin Yao. Construction and Catalysis Advances of Inorganic Chiral Nanostructures [J]. Acta Chimica Sinica, 2022, 80(11): 1507-1523.