Trifluoromethylthiolation/Oxidation of Styrenes for Facile Synthesis of α-Trifluoromethylthio Acetophenons

doi:10.6023/cjoc201807052

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (1): 232-237.DOI: 10.6023/cjoc201807052 Previous Articles Next Articles

Special Issue: 庆祝陈庆云院士九十华诞；元素有机化学合辑2018-2019

Articles

苯乙烯的氧化三氟甲硫基化反应

王建勇^a,b, 马岚^a, 李彦^a, 王细胜^a

a 中国科学技术大学化学系合肥微尺度物质科学国家研究中心合肥 230026;
b 齐鲁工业大学(山东省科学院)轻工科学与工程学院济南 250353

收稿日期:2018-07-27 修回日期:2018-10-25 发布日期:2018-11-12
通讯作者: 王细胜 E-mail:xswang77@ustc.edu.cn
基金资助:
国家自然科学基金（Nos.21602213，21522208）资助项目.

Trifluoromethylthiolation/Oxidation of Styrenes for Facile Synthesis of α-Trifluoromethylthio Acetophenons

Wang Jian-Yong^a,b, Ma Lan^a, Li Yan^a, Wang Xi-Sheng^a

a Hefei National Laboratory for Physical Sciences at the Microscale & Department of Chemistry, University of Science and Technology of China, Hefei 230026;
b School of Light Industry and Engineering, Qilu University of Technology(Shandong Academy of Sciences), Jinan 250353

Received:2018-07-27 Revised:2018-10-25 Published:2018-11-12
Contact: 10.6023/cjoc201807052 E-mail:xswang77@ustc.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21602213, 21522208).

1. Trifluoromethylthiolation/Oxidation of Styrenes for Facile Synthesis of α-Trifluoromethylthio Acetophenons.PDF(3770KB)

Abstract

Trifluoromethylthiolation/oxidation of styrenes with easiy-handling AgSCF₃ used as the trifluoromethylthiolating reagent has been described, which furnished a series of α-trifluoromethylthio acetophenons. A variety of substituted styrene could be bifunctionalized via radical process in a mixed solvent of dimethyl sulfoxide (DMSO) and CHCl₃, with potassium persulfate used as the oxidant under mild conditions. A simple and efficent method for the facile construction of various α-trifluoromethylthio acetophenons is thus demonstrated.

Key words: styrene, trifluoromethylthiolation, radical

Cite this article

Wang Jian-Yong, Ma Lan, Li Yan, Wang Xi-Sheng. Trifluoromethylthiolation/Oxidation of Styrenes for Facile Synthesis of α-Trifluoromethylthio Acetophenons[J]. Chin. J. Org. Chem., 2019, 39(1): 232-237.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Kirsch, P. Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim, 2004.
(b) O'Hagan, D.; Rzepa, H. S. Chem. Commun. 1997, 645.
(c) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(d) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359.
(e) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(f) Zhu, H.; Liu, G. Acta Chim. Sinica 2012, 70, 2404(in Chinese). (朱海涛, 刘国生, 化学学报, 2012, 70, 2404.)
(g) Lü, H.; Zhang, C.; Huang, J.; Zhao, Q.; Ma, Z.; Xiao, J. Acta Chim. Sinica 2012, 70, 1125(in Chinese). (吕会朝, 张成潘, 黄晋, 赵巧玲, 马志, 肖吉昌, 化学学报, 2012, 70, 1125.)
(h) 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.)
[2] (a) Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525.
(b) Yagupol'skii, L. M.; Il'chenko, A. Y.; Kondratenko, N. V. Russ. Chem. Rev. 1974, 43, 32.
(c) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
(d) Leroux, F.; Jeschke, P.; Schlosser, M. Chem. Rev. 2005, 105, 827.
(e) Manteau, B.; Pazenok, S.; Vors, J. P.; Leroux, F. R. J. Fluorine Chem. 2010, 131, 140.
[3] (a) Yarovenko, N. N.; Vasileva, A. S. J. Gen. Chem. USSR (Engl. Transl.) 1958, 28, 2537.
(b) Nodiff, E.; Lipschutz, A. S.; Craig, P. N.; Gordon, M. J. Org. Chem. 1960, 25, 60.
(c) Feiring, A. E. J. Org. Chem. 1979, 44, 2907.
[4] (a) Billard, T.; Blond, G.; Langlois, B. R. Tetrahedron Lett. 1997, 38, 65.
(b) Billard, T.; Blond, G.; Langlois, B. R. Tetrahedron Lett. 2001, 42, 2473.
(c) Kieltsch, I.; Eisenberger, P.; Togni, A. Angew. Chem., Int. Ed. 2007, 46, 754.
[5] (a) Chen, P.; Liu, G. Synthesis 2013, 45, 2919.
(b) Yang, X.; Wu, T.; Phipps, R. J.; Toste, F. D. Chem. Rev. 2015, 115, 826.
(c) He, W.-M.; Weng, Z.-Q. Prog. Chem. 2013, 25, 1071(in Chinese). (何伟明, 翁志强, 化学进展, 2013, 25, 1071.)
(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, C.; Chen, Q.; Shen, Q. Chin. J. Chem. 2016, 34, 495.
(f) Chen, C.; Fu, L.; Chen, P.; Liu, G. Chin. J. Chem. 2017, 35, 1781.
(g) 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.)
[6] (a) Chen, Q.-Y.; Duan, J.-X. J. Chem. Soc., Chem. Commun. 1993, 918.
(b) Zhang, C.-P.; Vicic, D. A. Chem. Asian J. 2012, 7, 1756.
(c) Chen, C.; Chu, L.-L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 12454.
(d) Weng, Z.; He, W.; Chen, C.; Lee, R.; Dan, D.; Lai, Z.; Kong, D.; Yuan, Y.; Huang, K.-W. Angew. Chem., Int. Ed. 2013, 52, 1548.
[7] Teverovskiy, G.; Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 7312.
[8] Chen, C.; Xie, Y.; Chu, L.; Wang, R.-W.; Zhang, X.; Qing, F. L. Angew. Chem., Int. Ed. 2012, 51, 2492.
[9] Zhang, C. P.; Vicic, D. A. J. Am. Chem. Soc. 2012, 134, 183.
[10] (a) Shao, X.; Wang, X.-Q.; Yang, T.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2013, 52, 3457.
(b) Pluta, R.; Nikolaienko, P.; Rueping, M. Angew. Chem., Int. Ed. 2014, 53, 1650.
[11] Yin, G.; Kalvet, I.; Englert, U.; Schoenebeck, F. J. Am. Chem. Soc. 2015, 137, 4164.
[12] Yin, F.; Wang, X.-S. Org. Lett. 2014, 16, 1128.
[13] Ma, L.; Cheng, X.-F.; Li, Y.; Wang, X.-S. Tetrahedron Lett. 2016, 57, 2972.
[14] (a) Zhang, C.-P.; Wang, Z.-L.; Chen, Q.-Y.; Zhang, C.-T.; Gu, Y.-C.; Xiao, J.-C. Chem. Commun. 2011, 47, 6632.
(b) Lu, Q.-Q.; Liu, C.; Huang, Z.-Y.; Ma, Y.-Y.; Zhang, J.; Lei, A.-W. Chem. Commun. 2014, 50, 14101.
(c) Wang, F.; Wang, D.-H.; Mu, X.; Chen, P.-H.; Liu, G. J. Am. Chem. Soc. 2014, 136, 10202.
[15] (a) Huang, Y.-J.; He, X.; Lin, X.-X.; Rong, M.-G.; Weng, Z.-Q. Org. Lett. 2014, 16, 3284.
(b) Huang, Y.-J.; He, X.; Li, H.-H.; Weng, Z.-Q. Eur. J. Org. Chem. 2014, 7324.
(c) Li, J.; Xie, F.-F.; Wang, P.-Q.; Wu, Q.-Y.; Chen, W.-D.; Ren, J.-M.; Zeng, B.-B. Tetrahedron 2015, 71, 5520.
(d) Wang, Y.-G.; You, Y.; Weng, Z.-Q. Org. Chem. Front. 2015, 2, 574.
(e) Wu, C.-Y.; Huang, Y.-J.; Chen, Z.-R.; Weng, Z.-Q. Tetrahedron Lett. 2015, 56, 3838.
[16] (a) Xu, C.; Ma, B.; Shen, Q. Angew. Chem., Int. Ed. 2014, 53, 9316.
(b) Alazet, S.; Zimmer, L.; Billard, T. Chem.-Eur. J. 2014, 20, 8589.
[17] Yadav, A. K.; Singh, K. N. Chem. Commun. 2018, 54, 1976.
[18] Arimori, S.; Takada, M.; Shibata, N. Org. Lett. 2015, 17, 1063.

苯乙烯的氧化三氟甲硫基化反应

Trifluoromethylthiolation/Oxidation of Styrenes for Facile Synthesis of α-Trifluoromethylthio Acetophenons

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Hong'en Tong, Hongyu Guo, Rong Zhou. Progress on Visible-Light Promoted Addition Reactions of Inert C—H Bonds to Carbonyls [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 54-69.
[2]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[3]	Yanshuo Zhu, Hongyan Wang, Penghua Shu, Ke'na Zhang, Qilin Wang. Recent Advances on Alkoxy Radicals-Mediated C(sp³)—H Bond Functionalization via 1,5-Hydrogen Atom Transfer [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 1-17.
[4]	Sijie Fan, Wuheng Dong, Caiyun Liang, Guichao Wang, Yao Yuan, Zuodong Yin, Zhaoguo Zhang. Visible Light-Induced Radical Cyclization for the Construction of 4-Aryl-1,2-dihydronaphthalenes [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3277-3286.
[5]	Jiantao Zhang, Cong Zhang, Nuolin Mo, Jiating Luo, Lianfen Chen, Weibing Liu. Research Progress in Radical Addition Reaction of Alkenes Involving Chloroform [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3098-3106.
[6]	Wei Xu, Hongbin Zhai, Bin Cheng, Taimin Wang. Visible Light-Induced Pd-Catalyzed Heck Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3035-3054.
[7]	Chunming Gui, Tongyao Zhou, Haifeng Wang, Qiongjiao Yan, Wei Wang, Jin Huang, Fener Chen. Recent Advances in Visible Light Photoredox-Catalyzed Alkynylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2647-2663.
[8]	Yu Zhao, Kai Zhang, Yubin Bai, Yantu Zhang, Shihui Shi. A Metal-Free Photocatalytic Hydrosilylation of Alkenes Using Bromide Salt as a Hydrogen Atom Transfer Reagent [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2837-2847.
[9]	Yingke Feng, He Wang, Mengxing Cui, Ran Sun, Xin Wang, Yang Chen, Lei Li. Visible-Light-Induced Difluoroalkylated Cyclization of Novel Functionalized Aromatic Isocyanides [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2913-2925.
[10]	Xiaona Yang, Hongyu Guo, Rong Zhou. Progress in Visible-Light Promoted Transformations of Organosilicon Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2720-2742.
[11]	Fen Huang, Weiwei Luo, Jun Zhou. Research Progress of Polychloroalkylation Based on C—H Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2368-2390.
[12]	Yu Tian, Juan Zhang, Wenchao Gao, Honghong Chang. Application of Dimethyl Sulfoxide as Methylating Reagent in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2391-2406.
[13]	Jiao Qin, Jie Chen, Yan Su. Synthesis of 2,2,6,6-Tetramethylpiperidin-1-yl-2-(2-cyanophenyl)-acetate by Transition Metal-Free Radical Cleavage Reaction from α-Bromoindanone [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2171-2177.
[14]	Jiamin Ma, Jiaoxiong Li, Qiansen Meng, Xianghua Zeng. Advances on the Radical Sulfonation of Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2040-2052.
[15]	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.