Synthesis of Substituted N—F Benzenesulfonimides and Comparison of Their Fluorination Reactivity via Their Reactions with Silylenol Ethers

doi:10.6023/cjoc201506014

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (12): 2604-2609.DOI: 10.6023/cjoc201506014 Previous Articles Next Articles

Articles

合成取代的N—F双苯磺酰亚胺及其与烯醇硅醚的反应比较

李青巍^a, 陈福利^a, 杨先金^a,b

a 华东理工大学精细化工研究所结构可控先进功能材料及其制备教育部重点实验室上海 200327;
b 中国科学院上海有机化学研究所有机氟化学重点实验室上海 200327

收稿日期:2015-06-12 修回日期:2015-07-13 发布日期:2015-08-17
通讯作者: 杨先金 E-mail:yxj@ecust.edu.cn
基金资助:
国家自然科学基金(No. 2132077)资助项目.

Synthesis of Substituted N—F Benzenesulfonimides and Comparison of Their Fluorination Reactivity via Their Reactions with Silylenol Ethers

Li Qingwei^a, Chen Fuli^a, Yang Xianjin^a,b

a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237;
b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2015-06-12 Revised:2015-07-13 Published:2015-08-17
Supported by:
Project supported by the National Natural Science Foundation of China (No. 2132077).

1. Synthesis of Substituted N—F Benzenesulfonimides and Comparison of Their Fluorination Reactivity via Their Reactions with Silylenol Ethers.PDF(1376KB)

Abstract

The fluorination reactivity of N—F benzenesulfonimides depended on the strength of N—F bond and was easily affected by substituents on the phenyl of substituted N—F benzenesulfonimides via electronic or steric effect. In this work, N—F benzenesulfonimides with different substituents were synthesized and reacted with silylenol ethers, and the results indicated that utilizing N-fluoro-4-fluoro-4'-nitrobenzenesulfonimide and N-fluoro-4-tert-butyl-4'-fluorobenzenesulfonimide could improve the reactivity or selectivity of fluorination than using N—F benzenesulfonimide in lots of selected experiments.

Key words: substituted N—F benzenesulfonimide, fluorination, silylenol ether

Cite this article

Li Qingwei, Chen Fuli, Yang Xianjin. Synthesis of Substituted N—F Benzenesulfonimides and Comparison of Their Fluorination Reactivity via Their Reactions with Silylenol Ethers[J]. Chin. J. Org. Chem., 2015, 35(12): 2604-2609.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Shimizu, M.; Hiyama, T. Angew. Chem., Int. Ed. 2005, 44, 214.
[2] Welch, J. T. Tetrahedron 1987, 43, 3123.
[3] Ni, C.; Zhu, L.; Hu, J. Acta Chim. Sinica 2015, 73, 90 (in Chinese). (倪传法, 朱林桂, 胡金波, 化学学报, 2015, 73, 90.)
[4] Zhang, J.; Jin, C.; Zhang, Y. Chin. J. Org. Chem. 2014, 34, 662 (in Chinese). (张霁, 金传飞, 张英俊, 有机化学, 2014, 34, 662.)
[5] Wang, G.; He, X.; Dai, 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.)
[6] 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.)
[7] Differding, E.; Lang, R. W. Tetrahedron Lett. 1988, 29, 6087.
[8] Differding, E.; Ofner, H. Synlett 1991, 187.
[9] Davis, F. A.; Zhou, P.; Murphy, C. K. Tetrahedron Lett. 1993, 34, 3971.
[10] Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96,1737.
[11] (a) Purrington, S. T.; Kagen, B. S.; Patrick, T. B. Chem. Rev. 1986, 86, 997. (b) Liu, C.-B.; Ma, H.; Nie, J.; Ma, J.-A. Chin. J. Chem. 2012, 30, 47.
[12] Banks, R. E.; Mohialdin-Khaffaf, S. N.; Lal, G. S.; Sharif, I.; Syvret, R. G. J. Chem. Soc., Chem. Commun. 1992, 595.
[13] Umemoto, T.; Fukami, S.; Tomizawa, G.; Harasawa, K.; Kawada, K.; Tomita, K. J. Am. Chem. Soc. 1990, 112, 8563.
[14] Ishimaru, T.; Shibata, N.; Horikawa, T.; Yasuda, N.; Nakamura, S.; Toru, T.; Shiro, M. Angew. Chem., Int. Ed. 2008, 47, 4157.
[15] (a) Greedy, B.; Paris, J. M.; Vidal, T.; Gouverneur, V. Angew.Chem. 2003, 115, 3413. (b) Zhang, R.; Wang, D.; Xu, Q.; Jiang, J.-J.; Shi, M. Chin. J. Chem. 2012, 30, 1295.
[16] Shibatomi, K.; Yamamoto, H. Angew. Chem., Int. Ed. 2008, 47, 5796.
[17] Yasui, H.; Yamamoto, T.; Ishimaru, T.; Fukuzumi, T.; Tokunaga, E.; Akikazu, K.; Shiro, M.; Shibata, N. J. Fluorine Chem. 2011, 132, 222.
[18] Zhu, C.-L.; Maeno, M.; Zhang, F.-G.; Shigehiro, T.; Kagawa, T.; Kawada, K.; Shibata, N.; Ma, J.-A.; Cahard, D. Eur. J. Org. Chem. 2013, 29, 6501.
[19] Shunatona, H. P.; Frh, N.; Wang, Y. M.; Rauniyar, V.; Toste, F. D. Angew. Chem. Int. Ed. 2013, 52, 7724.
[20] Chen, G. L.; Chen, F. L.; Zhang, Y. ; Yang, X. Y.; Yuan, X. M.; Wu, F. H.; Yang, X. J. J. Fluorine Chem. 2012, 133, 155.
[21] Zhang, Y.; Yang, X. J.; Xie, T.; Chen, G. L.; Zhu, W. H.; Zhang, X. Q.; Yang, X. Y.; Wu, X. Y.; He, X. P.; He, H. M. Tetrahedron 2013, 69, 4933.
[22] Wang, F.-J.; Li, J.-L.; Hu, Q.-Y.; Yang, X.-J.; Wu, X.-Y.; He, H.-M. Eur. J. Org. Chem.2014, 17, 3607.
[23] Dykhanov, N. N. Zh. Obshch. Khim. 1959, 29, 3602.
[24] Busto, E.; Gotor-Fernández, V.; Gotor, V. J. Org. Chem. 2012, 77, 4842.
[25] Teare, H.; Robins, G. E.; Arstad, E.; Luthra, S. K.; Gouverneur, V. Chem. Commun. 2007, 2330.
[26] Xu, J.; Hu, Y.; Huang, D.; Wang, K. H.; Xu, C.; Niu, T. Adv. Synth. Catal. 2012, 354, 515.
[27] Cahard, D.; Audouard, C.; Plaquevent, J. C.; Roques, N. Org. Lett. 2000, 2, 3699.
[28] Stavber, S.; Šket, B.; Zajc, B.; Zupan, M. Tetrahedron 1989, 45, 6003.
[29] Zhao, Y.; Pen, Y.; Liu, H.; Yang, Y.; Jiang, Z.; Tang, C. Chem. Eur. J. 2011, 17, 3571.
[30] Stavber, S.; Jereb, M.; Zupan, M. Synthesis 2002, 2609.

合成取代的N—F双苯磺酰亚胺及其与烯醇硅醚的反应比较

Synthesis of Substituted N—F Benzenesulfonimides and Comparison of Their Fluorination Reactivity via Their Reactions with Silylenol Ethers

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Qiuyu Gu, Tianyu Peng, Mingcheng Bo, Yifeng Wang. Selective Mono- and Di-deuterodefluorination of Trifluoroacetamides Promoted by Boryl Radicals [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1832-1842.
[2]	Chengfu Zeng, Yuan He, Qing Li, Lin Dong. Ir(III)-Catalyzed Novel Three-Component Cascade Trifluoroethoxylation and One-Pot Method to Construct Complex Amide Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1115-1123.
[3]	Longyu Ran, Chengpan Zhang. An Overview of the Reactions with Trifluoromethyl Trifluoromethanesulfonate [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2045-2054.
[4]	Xiang Li, Yifan Zhang, Kailin Lu, Shihui Liu, Yongqiang Zhang. Aminofluorination-Based Structural Modification of Curcumol for the Construction of 3D-Shaped Natural Product Fragment Library [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2124-2133.
[5]	Jun Pan, Jingjing Wu, Fanhong Wu. Progress in Fluoroalkylation of Multicomponent [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 983-1001.
[6]	Weilin Wang, Weidong Chen, Junfei Luo, Pan Xie. Recent Advances in C—H Fluorination and Amination with N-Fluorobenzenesulfonimide [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 543-552.
[7]	Chen Qianwen, Yang Yaocheng, Wang Xia, Zhang Qian, Li Dong. Hypervalent Iodine Reagent-Mediated C(5) C-H Nucleophilic Fluorination of 8-Aminoqunolines [J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 454-461.
[8]	Zhang Huaiyuan, Tang Rongping, Shi Xingli, Xie Lin, Wu Jiawei. Recent Advances in Organic Electrochemical Synthesis and Application of Hypervalent Iodine Reagents [J]. Chin. J. Org. Chem., 2019, 39(7): 1837-1845.
[9]	Liang Long, Liu Li-Na, Chen Xue-Qiang, Xiang Xuan, Ling Jun, Lu Zheng-Quan, Li Jing-Jing, Li Wei-Shi. Benzodithiophene/Benzothiadiazole-Based ADA-Type Optoelectronic Molecules: Influence of Fluorine Substitution [J]. Chin. J. Org. Chem., 2019, 39(1): 157-169.
[10]	Wu Wensheng, Yuan Hang, Huang Gaokui, Jiang Chunhui, Lu Hongfei. Fluorination of β-Ketoesters and β-Ketoamides Based on PhI(OAc)₂ [J]. Chin. J. Org. Chem., 2019, 39(1): 137-143.
[11]	Liu Qingquan, Hu Xiangguo. Application of Benzylic C-H Fluorination for the Formal Synthesis of syn-α, β-Difluoro-γ-amino Acid [J]. Chin. J. Org. Chem., 2018, 38(6): 1525-1529.
[12]	Huang Yulin, Chen Qian. Fluorination Reaction of P(Ⅲ) Compounds with the Electrophilic Fluorinating Reagent Selectfluor [J]. Chin. J. Org. Chem., 2017, 37(10): 2745-2751.
[13]	He Jiangqi, Lou Shaojie, Xu Danqian. Recent Advances in Transition-Metal Catalyzed C—H Bond Fluorination [J]. Chin. J. Org. Chem., 2016, 36(6): 1218-1228.
[14]	Xia Ran, Guo Zhen, Qin Bowen, Ji Zhiyue, Xie Mingsheng, Qu Guirong, Guo Haiming. A New Method for the Synthesis of Clofarabine [J]. Chin. J. Org. Chem., 2014, 34(6): 1154-1160.
[15]	Zhang Ji, Jin Chuanfei, Zhang Yingjun. Recent Advances in Research and Development of Fluorinated Drugs and New Methods for Fluorination, Mono-, Di-and Tri-fluoromethylation [J]. Chin. J. Org. Chem., 2014, 34(4): 662-680.