High Efficient Synthesis of Monofluoromethyldisulfides

doi:10.6023/cjoc202009001

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1117-1123.DOI: 10.6023/cjoc202009001 Previous Articles Next Articles

ARTICLES

一氟甲基二硫化物的高效合成

胡晓光^a, 庞仁艺^a, 郑天骄^a, 姚瑞超^a, 陈文博^a^,^b^,^*()

a 上海电力大学环境与化学工程学院上海市电力材料防护与新材料重点实验室上海 200090
b 中国科学院上海有机化学研究所中科院能量调控材料重点实验室上海 200032

收稿日期:2020-09-01 修回日期:2020-11-02 发布日期:2020-12-01
通讯作者: 陈文博
基金资助:
上海市自然科学基金(20ZR1471600); 上海市科学技术委员会(19DZ2271100); 中国科学院能量调控材料重点实验室开放基金(ORFP2020-06)

High Efficient Synthesis of Monofluoromethyldisulfides

Xiaoguang Hu^a, Renyi Pang^a, Tianjiao Zheng^a, Ruichao Yao^a, Wenbo Chen^a^,^b^,^*()

a Shanghai Key Laboratory of Materials Protection and Advanced Materials in Electric Power, College of Environmental and Chemical Engineering, Shanghai University of Electric Power, Shanghai 200090
b CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2020-09-01 Revised:2020-11-02 Published:2020-12-01
Contact: Wenbo Chen
About author:
* Corresponding author. E-mail: wenbochen@shiep.edu.cn
Supported by:
Natural Science Foundation of Shanghai(20ZR1471600); Science and Technology Commission of Shanghai Municipality(19DZ2271100); Open Research Fund Program of CAS Key Laboratory Of Energy Regulation Materials(ORFP2020-06)

1. cjoc202009001辅助材料.pdf(3496KB)

Abstract

The monofluoromethylthiolation reaction of thiophenols/mercaptans was developed at room temperature using PhSO₂SCH₂F as monofluoromethylthiolation reagent, and a series of monofluoromethyl disulfides were synthesized in good yields. This method features short reaction time, mild conditions, simple operation and no additives. It provides a simple and convenient way for the efficient preparation of monofluoromethyl disulfides.

Key words: monofluoromethylthio, disulfide, PhSO₂SCH₂F, thiophenol

Cite this article

Xiaoguang Hu, Renyi Pang, Tianjiao Zheng, Ruichao Yao, Wenbo Chen. High Efficient Synthesis of Monofluoromethyldisulfides[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1117-1123.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 6

References 15

[1]	(a) Zhang, P. P.; Lu, L.; Shen, Q. L. Acta Chim. Sinica 2017, 75, 744. (in Chinese) pmid: 28704047
	(张盼盼, 吕龙, 沈其龙, 化学学报, 2017, 75, 744.) pmid: 28704047
	(b) Geng, Y.; Liang, A. P.; Gao, X. Y.; Niu, C. S.; Li, J. Y.; Zou, D.P; Wu, Y. S.; Wu, Y. J. J. Org. Chem. 2017, 82, 8604. pmid: 28704047
[2]	(a) Yang, X. Y.; Wu, T.; Phipps, R. J.; Toste, F. D. Chem. Rev. 2015, 115, 826. pmid: 25337896
	(b) Yan, Q.; Jiang, L. P.; Yi, W. B. Chin. J. Org. Chem. 2020, 40, 1. (in Chinese) doi: 10.6023/cjoc201907028 pmid: 25337896
	(闫强, 蒋绿齐, 易文斌, 有机化学, 2020, 40, 1.) pmid: 25337896
[3]	(a) Leroux, F.; Jeschke, P.; Schlosser, M. Chem. Rev. 2005, 105, 827. doi: 10.1021/cr040075b pmid: 23738814
	(b) Boiko, V. N. Beilstein J. Org. Chem. 2010, 6, 880. doi: 10.3762/bjoc.6.88 pmid: 23738814
	(c) He, W. M.; Weng, Z. Q. Prog. Chem. 2013, 25, 1071. (in Chinese) pmid: 23738814
	(何伟明, 翁志强, 化学进展, 2013, 25, 1071.) pmid: 23738814
	(d) Wang, Z.; Tu, Q.; Weng, Z. J. Organomet. Chem. 2014, 751, 830. pmid: 23738814
	(e) Nikolaienko, P.; Pluta, R.; Rueping, M. Chem.-Eur. J. 2014, 20, 9867. doi: 10.1002/chem.201402679 pmid: 23738814
	(f) Li, S. S.; Wang, J. B. Acta Chim. Sinica 2018, 76, 913. (in Chinese) 2d961da2-63cb-468b-901e-8be1ecb27261 doi: 10.6023/A18070306 pmid: 23738814
	(李树森, 王剑波, 化学学报, 2018, 76, 913.) 2d961da2-63cb-468b-901e-8be1ecb27261 doi: 10.6023/A18070306 pmid: 23738814
	(g) Yang, Y. D.; Azuma, A.; Tokunaga, E.; Yamasaki, M.; Shiro, M.; Shibata, N. J. Am. Chem. Soc. 2013, 135, 8782. pmid: 23738814
	(h) Shao, X. X.; Wang, X. Q.; Yang, T.; Lu, L.; Shen, Q. L. Angew. Chem.. Int. Ed. 2013, 52, 1. pmid: 23738814
	(i) Zhu, D. H.; Shao, X. X.; Hong, X.; Lu, L.; Shen, Q. L. Angew. Chem.. Int. Ed. 2016, 55, 15807. pmid: 23738814
[4]	(a) Zhao, X.; Li, T. J.; Yang, B.; Qiu., D.; Lu, K. Tetrahedron 2017, 73, 3112.
	(b) Ismalaj, E.; Billard, T. J. Fluorine Chem. 2017, 203, 215.
	(c) Xu, B.; Wang, D. C.; Hu, Y. H.; Shen, Q. L. Org. Chem. Front. 2018, 5, 1462.
[5]	(a) Howland, W. C. Clin. Exp Allergy 1996, 26, 18. pmid: 8735854
	(b) Zhou, J.; Jin, C.; Su, W. Org. Process Res. Dev. 2014, 18, 928. pmid: 8735854
[6]	Ashton, M. J.; Lawrence, C.; Karlsson, J. A.; Stuttle, K. A. J.; Newton, C. G.; Vacher, B. Y. J.; Webber, S.; Withnall, M. J. J. Med. Chem. 1996, 39, 4888. pmid: 8960547
[7]	Jung, M.; Wahl, A. F.; Neupert, W.; Geisslinger, G.; Senter, P. D. Pharm. Pharmacol. Commun. 2000, 6, 217. doi: 10.1211/146080800128735926
[8]	(a) Zhao, Q. C.; Lu, L.; Shen, Q. L. Angew. Chem. 2017, 129, 11733. doi: 10.1002/ange.v129.38 pmid: 30226061
	(b) Liu, F. M.; Jiang, L. Q.; Qiu, H. Y.; Yi, W. B. Org. Lett. 2018, 20, 6270. pmid: 30226061
[9]	(a) Guo, S. H.; Wang, M. Y.; Pan, G. F.; Zhu, X. Q.; Gao, Y. R.; Wang, Y. Q. Adv. Synth. Catal. 2018, 360, 1861.
	(b) Xu, B.; Li, D. Z.; Lu, L.; Wang, D. C.; Hu, Y. H.; Shen, Q. L. Org. Chem. Front. 2018, 5, 2163.
[10]	Pang, R. Y.; Yao, R. C.; Lu, S. Y.; Zhou, Y. C.; Chen, W. B. Chin. Chem. Lett. 2021, 32, 453.
[11]	Wang, W. G.; Lin, Y. Z.; Ma, Y. D.; Tung, C. H.; Xu, Z. H. Org. Lett. 2018, 20, 3829. pmid: 29920107
[12]	(a) Cheng, Z.; Zhang, J.; Ballou, D. P.; Williams, C. H. , Jr. Chem. Rev. 2011, 111, 5768. pmid: 29875443
	(b) Block, E.; Bayer, T.; Naganathan, S.; Zhao, S. H. J. Am. Chem. Soc. 1996, 118, 2799. doi: 10.1021/ja953444h pmid: 29875443
	(c) Chankhamjon, P.; Boettger-Schmidt, D.; Scherlach, K.; Urbansky, B.; Lackner, G.; Kalb, D.; Dahse, H.-M.; Hoffmeister, D.; Hertweck, C. Angew. Chem.. Int. Ed. 2014, 53, 13409. doi: 10.1002/anie.201407624 pmid: 29875443
	(d) Xiao, X.; Xue, J.; Jiang, X. Nat. Commun. 2018, 9, 2191. pmid: 29875443
[13]	(a) Sonia, T. V.; Erben, M. F.; Boese, R.; Vedova, C. O. New J. Chem. 2010, 34, 1365. doi: 10.1039/b9nj00382g pmid: 25382258
	(b) Pluta, R.; Rueping, M. Chem.-Eur. J. 2014, 20, 17315. pmid: 25382258
	(c) Glenadel, Q.; Billard, T. Chin. J. Chem. 2016, 34, 455. pmid: 25382258
[14]	(a) Xu, C.; Ma, B.; Shen, Q. L. Angew. Chem.. Int. Ed. 2014, 53, 9316. pmid: 26178409
	(b) Zhu, D. H.; Gu, Y.; Lu, L.; Shen, Q. L. J. Am. Chem. Soc. 2015, 137, 10547. pmid: 26178409
[15]	Huang, P. F.; Wang, P.; Tang, S.; Fu, Z. J.; Lei, A. W. Angew. Chem. 2018, 130, 8247. doi: 10.1002/ange.v130.27

Entry	n(1a)∶n(2)	Solvent^b	Yield^a/%
1	1.5∶1	DCM	55
2	1∶1	DCM	81
3	1∶1.5	DCM	89
4	1∶1.5	THF	95
5	1∶1.5	CH₃CN	89
6	1∶1.5	DCE	90
7	1∶1.5	EA	87
8	1∶1.5	MeOH	85
9	1∶1.5	EtOH	86
10	1∶1.5	DMSO	79
11	1∶1.5	DMF	66
12^c	1∶1.5	THF	96

Entry	n(1a)∶n(2)	Solvent^b	Yield^a/%
1	1.5∶1	DCM	55
2	1∶1	DCM	81
3	1∶1.5	DCM	89
4	1∶1.5	THF	95
5	1∶1.5	CH₃CN	89
6	1∶1.5	DCE	90
7	1∶1.5	EA	87
8	1∶1.5	MeOH	85
9	1∶1.5	EtOH	86
10	1∶1.5	DMSO	79
11	1∶1.5	DMF	66
12^c	1∶1.5	THF	96

一氟甲基二硫化物的高效合成

High Efficient Synthesis of Monofluoromethyldisulfides

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 6

References 15

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jiyu Liu, Shengyu Li, Kuan Chen, Yin Zhu, Yuan Zhang. Triphenylamine-Based Ordered Mesoporous Polymer as a Metal-Free Photocatalyst for Oxidation of Thiols to Disulfide [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 605-612.
[2]	Jiawei Huang, Xiaoman Li, Liang Xu, Yu Wei. Electrochemical Decarboxylation Coupling of α-Keto Acids with Thiophenols: A New Avenue for the Synthesis of Thioesters [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 756-762.
[3]	Fei Cheng, Qiwen Sun, Jiangrong Lu, Xinglan Wang, Jiquan Zhang. Research Progress on the Construction of C—S Bond Using Aryl Disulfides as Radical Sulfur Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3728-3744.
[4]	Yannan Ma, Ya'ni Liu, Jinyan Wang, Xitong Chen, Hao Yin, Qiaona Chi, Shixi Jia, Shanshan Du, Yunkun Qi, Kewei Wang. DIC/Oxyma Based Efficient Synthesis and Activity Evaluation of Spider Peptide Toxin GsMTx4 [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 498-506.
[5]	Ningbo Li, Li Xu, Rong Ma, Qi Fan, Bo Li, Jie Qiao, Rui Guo, Xinhua Xu. Synthesis and Antitumor Activities of Novel Organic Sulfur (Selenium) Tegafur Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2723-2734.
[6]	Jinyan Wang, Liying Dong, Ya'ni Liu, Xitong Chen, Yannan Ma, Hao Yin, Shanshan Du, Yunkun Qi, Kewei Wang. Efficient Synthesis and Oxidative Folding Studies of Centipede Toxin RhTx [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2800-2809.
[7]	Liu Aiyao, Liu Jiang, Mei Haibo, Röschenthaler Gerd-Volker, Han Jianlin. Selectfluor-Promoted Twofold Sulfination of Alcohols for the Synthesis of Sulfinic Ester from Diaryldisulfides [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 1926-1933.
[8]	Jiang Xiaoying, Yao Chuansheng, Tong Chuo, Bai Renren, Zhou Tao, Xie Yuanyuan. Selective Oxidation of Sulfides/Disulfides to Sulfoxides/ Thiosulfonates Using t-Butyl Hydroperoxide (TBHP) without Catalyst [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1752-1759.
[9]	Yan Qiang, Jiang Lüqi, Yi Wenbin. Recent Progress on Direct Difluoromethylthiolation and Monofluoromethylthiolation [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 1-14.
[10]	Yang Ying, Balati Hasimujiang, Abulikemu Abudu Rexit. Research on Reduction of α,α,α-Tribromomethyl Ketones via Thiophenol [J]. Chin. J. Org. Chem., 2019, 39(3): 727-733.
[11]	Lu Lulu, Zhou Bingwei, Jin Hongwei, Liu Yunkui. Radical-Triggered Tandem Reaction of Vinyl Azides with Isopropylxanthic Disulfide for the Synthesis of 6-Sulfanylmethyl Phenanthridines [J]. Chin. J. Org. Chem., 2019, 39(2): 515-520.
[12]	Lin Yamei, Yi Wenbin. A Route to Alkynyl Sulfides and Asymmetric Disulfides from Sodium Arylsulfiniate [J]. Chin. J. Org. Chem., 2018, 38(5): 1207-1213.
[13]	Jing Lia, Jin Huia, Guan Meib, Wu Xiaohuaa, Wang Qiantaoa, Wu Yonga. Metal-Free Oxidation of Thiols by N-Fluorobenzenesulfonimide: A Rapid and Efficient Method to Synthesize Disulfides [J]. Chin. J. Org. Chem., 2018, 38(3): 692-697.
[14]	Ge Weiwei, Chen Jing, Zhang Ye, Zong Liang, Zhang Ming, Dong Junjun. Semiregioselective Formation of Linaclotide with Orthogonal Cysteine Protection Strategy [J]. Chin. J. Org. Chem., 2017, 37(9): 2409-2415.
[15]	An Yanni, Li Jianxiao, Li Meng, Li Chunsheng, Yang Shaorong. N-Iodosuccinimide-Promoted Regioselective Arylsulfenylation of Imidazo[1,2-a]pyridines with Disulfides [J]. Chin. J. Org. Chem., 2017, 37(3): 720-725.