Recent Advance in Asymmetric Trifluoromethylthiolation
- Corresponding author: Wang Jianbo, wangjb@pku.edu.cn
Citation: Li Shu-Sen, Wang Jianbo. Recent Advance in Asymmetric Trifluoromethylthiolation[J]. Acta Chimica Sinica, ;2018, 76(12): 913-924. doi: 10.6023/A18070306
(a) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359. (b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. (c) Manteau, B.; Pazenok, S.; Vors, J.-P.; Leroux, F. R. J. Fluorine Chem. 2010, 131, 140. (d) Gillis, E. P.; Eastman, K. J.; Hill, M. D.; Donnelly, D. J.; Meanwell, N. A. J. Med. Chem. 2015, 58, 8315.
(a) Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525. (b) Hansch, C.; Leo, A.; Unger, S. H.; Kim, K. H.; Nikaitani, D.; Lien, E. J. J. Med. Chem. 1973, 16, 1207.
For recent reviews on trifluoromethylthiolation, see: (a) Toulgoat, F.; Alazet, S.; Billard, T. Eur. J. Org. Chem. 2014, 2014, 2415. (b) Shao, X.; Xu, C.; Lu, L.; Shen, Q. Acc. Chem. Res. 2015, 48, 1227. (c) Xu, X.-H.; Matsuzaki, K.; Shibata, N. Chem. Rev. 2015, 115, 731. (d) Zhang, K.; Xu, X.; Qing, F. Chin. J. Org. Chem. 2015, 35, 556(in Chinese). (张柯, 徐修华, 卿凤翎, 有机化学, 2015, 35, 556.) (e) Xu, J.; Chen, P.; Ye, J.; Liu, G. Acta Chim. Sinica 2015, 73, 1294(in Chinese). (徐佳斌, 陈品红, 叶金星, 刘国生, 化学学报, 2015, 73, 1294.) (f) Zheng, H.; Huang, Y.; Weng, Z. Tetrahedron Lett. 2016, 57, 1397. (g) Li, G.; Sun, D. Chin. J. Org. Chem. 2016, 36, 1715(in Chinese). (李恭铭, 孙德群, 有机化学, 2016, 36, 1715). (h) Barata-Vallejo, S.; Bonesi, S.; Postigo, A. Org. Biomol. Chem. 2016, 14, 7150. (i) Guo, Y.; Huang, M.-W.; Fu, X.-L.; Liu, C.; Chen, Q.-Y.; Zhao, Z.-G.; Zeng, B.-Z.; Chen, J. Chin. Chem. Lett. 2017, 28, 719. (j) Zhang, P.; Lu, L.; Shen, Q. Acta Chim. Sinica 2017, 75, 744(in Chinese). (张盼盼, 吕龙, 沈其龙, 化学学报, 2017, 75, 744.)(k)Zhao, X.; Li, T.; Tian, M.; Su, Z.; Wei, A.; Lu, K. Chin. J. Org. Chem. 2018, 38, 677(in Chinese). (赵霞, 李天骄, 田苗苗, 苏志扬, 魏奥琪, 芦逵, 有机化学, 2018, 38, 677.)
Bootwicha, T.; Liu, X.; Pluta, R.; Atodiresei, I.; Rueping, M. Angew. Chem., Int. Ed. 2013, 52, 12856.
doi: 10.1002/anie.201304957
Wang, X.; Yang, T.; Cheng, X.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 12860.
doi: 10.1002/anie.201305075
Rueping, M.; Liu, X.; Bootwicha, T.; Pluta, R.; Merkens, C. Chem. Commun. 2014, 50, 2508.
doi: 10.1039/c3cc49877h
Zhu, X.-L.; Xu, J.-H.; Cheng, D.-J.; Zhao, L.-J.; Liu, X.-Y.; Tan, B. Org. Lett. 2014, 16, 2192.
doi: 10.1021/ol5006888
Yang, T.; Shen, Q.; Lu, L. Chin. J. Chem. 2014, 32, 678.
doi: 10.1002/cjoc.201400392
Liao, K.; Zhou, F.; Yu, J.-S.; Gao, W.-M.; Zhou, J. Chem. Commun. 2015, 51, 16255.
doi: 10.1039/C5CC07010D
Zhao, B.-L.; Du, D.-M. Org. Lett. 2017, 19, 1036.
doi: 10.1021/acs.orglett.6b03846
Li, M.; Xue, X.-S.; Cheng, J.-P. ACS Catal. 2017, 7, 7977.
doi: 10.1021/acscatal.7b03007
Deng, Q.-H.; Rettenmeier, C.; Wadepohl, H.; Gade, L. H. Chem.-Eur. J. 2014, 20, 93.
doi: 10.1002/chem.201303641
Jin, M. Y.; Li, J.; Huang, R.; Zhou, Y.; Chung, L. W.; Wang, J. Chem. Commun. 2018, 54, 4581.
doi: 10.1039/C8CC02097C
Zhang, H.; Leng, X.; Wan, X.; Shen, Q. Org. Chem. Front. 2017, 4, 1051.
doi: 10.1039/C7QO00042A
Chachignon, H.; Kondrashov, E. V.; Cahard, D. Adv. Synth. Catal. 2018, 360, 965.
doi: 10.1002/adsc.v360.5
Liu, X.; An, R.; Zhang, X.; Luo, J.; Zhao, X. Angew. Chem., Int. Ed. 2016, 55, 5846.
doi: 10.1002/anie.201601713
Luo, J.; Liu, Y.; Zhao, X. Org. Lett. 2017, 19, 3434.
doi: 10.1021/acs.orglett.7b01392
Luo, J.; Cao, Q.; Cao, X.; Zhao, X. Nat. Commun. 2018, 9, 527.
doi: 10.1038/s41467-018-02955-0
Liu, X.; Liang, Y.; Ji, J.; Luo, J.; Zhao, X. J. Am. Chem. Soc. 2018, 140, 4782.
doi: 10.1021/jacs.8b01513
Zhang, Z.; Sheng, Z.; Yu, W.; Wu, G.; Zhang, R.; Chu, W.-D.; Zhang, Y.; Wang, J. Nat. Chem. 2017, 9, 970.
doi: 10.1038/nchem.2789
Xu, L.; Wang, H.; Zheng, C.; Zhao, G. Adv. Synth. Catal. 2017, 359, 2942.
doi: 10.1002/adsc.v359.17
Hock, K. J.; Koenigs, R. M. Angew. Chem., Int. Ed. 2017, 56, 13566.
doi: 10.1002/anie.201707092
Mao, G.; Chen, L.; Wang, C. Sci. China Chem. 2017, 60, 1565.
doi: 10.1007/s11426-017-9113-5
Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu3+ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
Qiuyang LUO , Xiaoning TANG , Shu XIA , Junnan LIU , Xingfu YANG , Jie LEI . Application of a densely hydrophobic copper metal layer in-situ prepared with organic solvents for protecting zinc anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1243-1253. doi: 10.11862/CJIC.20240110
Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414
Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
Jiakun BAI , Ting XU , Lu ZHANG , Jiang PENG , Yuqiang LI , Junhui JIA . A red-emitting fluorescent probe with a large Stokes shift for selective detection of hypochlorous acid. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1095-1104. doi: 10.11862/CJIC.20240002
Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO2 by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO2 mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
Ruiqing LIU , Wenxiu LIU , Kun XIE , Yiran LIU , Hui CHENG , Xiaoyu WANG , Chenxu TIAN , Xiujing LIN , Xiaomiao FENG . Three-dimensional porous titanium nitride as a highly efficient sulfur host. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 867-876. doi: 10.11862/CJIC.20230441
Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169