Research Progress in Synthesis and Application of Thiosulfonates

doi:10.6023/cjoc202203036

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (8): 2322-2330.DOI: 10.6023/cjoc202203036 Previous Articles Next Articles

REVIEW

硫代磺酸酯的合成与应用研究进展

宇世伟, 陈兆华, 陈淇, 林舒婷, 何金萍, 陶冠燊, 汪朝阳^*()

华南师范大学化学学院教育部环境理论化学重点实验室广州市生物医学分析化学重点实验室 GDMPA手性药物过程控制与质量评价重点实验室广州 510006

收稿日期:2022-03-18 修回日期:2022-04-21 发布日期:2022-05-26
通讯作者: 汪朝阳
基金资助:
广东省基础与应用基础研究基金(2021A1515012342); 广东省科技计划(2017A010103016); 华南师范大学专项人才培养计划([2021]72); 广东省质量工程建设项目专项人才培养计划资助项目([2021]29)

Research Progress in Synthesis and Application of Thiosulfonates

Shiwei Yu, Zhaohua Chen, Qi Chen, Shuting Lin, Jinping He, Guanshen Tao, Zhaoyang Wang()

GDMPA Key Laboratory for Process Control and Quality Evaluation of Chiral Pharmaceuticals;Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine;Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education;School of Chemistry, South China Normal University, Guangzhou 510006

Received:2022-03-18 Revised:2022-04-21 Published:2022-05-26
Contact: Zhaoyang Wang
Supported by:
Guangdong Basic and Applied Basic Research Foundation(2021A1515012342); Guangdong Provincial Science and Technology Project(2017A010103016); Special Talent Training Program of South China Normal University([2021]72); Guangdong Province Quality Engineering Construction Project for Special Talent Training Plan([2021]29)

As an important kind of synthons, thiosulfonates can react with alkynes, alkenes, aldehydes, and halogenated hydrocarbons to synthesize thioethers and sulfones. At the same time, some thiosulfonate compounds have anti-viral and anti-fungal bioactivities. The synthesis of thiosulfonates and their applications in organic synthesis have been under the spotlight. Thus, according to different types of catalysts and new progress in green chemistry, the synthesis progress of thiosulfonates is summarized. On the other hand, according to the types of reactants and reaction types, the application progress of thiosulfonates in organic synthesis is reviewed. In the future, among the researches on the construction of new sulfides with thiosulfonates, various difunctionalization reactions are still promising directions.

Key words: thiosulfonate, green chemistry, C—S bond formation, photocatalysis, radical reaction, difunctionalization reaction

Cite this article

Shiwei Yu, Zhaohua Chen, Qi Chen, Shuting Lin, Jinping He, Guanshen Tao, Zhaoyang Wang. Research Progress in Synthesis and Application of Thiosulfonates[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2322-2330.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 8

Scheme 1. Synthesis of thiosulfonate compounds from sulfonyl chlorides in different copper salt/ligand/reductant systems

Scheme 2. Synthesis reaction of symmetrical/unsymmetrical thiosulfonate compounds from sulfinamides

Scheme 3. Synthesis of symmetrical/unsymmetrical thiosulfonate compounds from sodium sulfinates mediated by BF3•OEt2

Scheme 4. Synthesis reaction of trifluoromethyl thiosulfonate compounds from sulfonyl chlorides

Scheme 5. Synthesis of thiosulfonates and disulfides from sulfonyl chlorides mediated by tetrabutylammonium iodide

Scheme 6. Synthesis of vinyl sulfones compounds from thiosulfonate and alkyne

Scheme 7. Copper(I)-catalyzed tandem reaction of 5-thio triazoles compounds from alkyne and azidothiosulfonate

Scheme 8. Visible-light promoted cross-coupling reactions of aryldiazonium salts and S-methyl-d3 thiosulfonate

References 118

[1]	Koning, N. R.; Sundin, A. P.; Strand, D. J. Am. Chem. Soc. 2021, 143, 21218. doi: 10.1021/jacs.1c10364
[2]	Laxmikeshav, K.; Kumari, P.; Shankaraiah, N. Med. Res. Rev. 2022, 42, 513. doi: 10.1002/med.21852
[3]	Chen, S. H.; Jiang, K.; Lin, J. Y.; Yang, K.; Cao, X. Y.; Luo, X. Y.; Wang, Z. Y. J. Mater. Chem. C 2020, 8, 8257. doi: 10.1039/D0TC01870H
[4]	Michalland, J.; Casaretto, N.; Zard, S. Z. A. Angew. Chem., Int. Ed. 2021, 61. e202113333.
[5]	Mampuys, P.; McElroy, C. R.; Clark, J. H.; Orru, R. V. A.; Maes, B. U. W. Adv. Synth. Catal. 2020, 362, 3. doi: 10.1002/adsc.201900864
[6]	Wang, F.; Liu, B. X.; Rao, W. D.; Wang, S. Y. Org. Lett. 2020, 22, 6600. doi: 10.1021/acs.orglett.0c02370 pmid: 32806158
[7]	Merchant, R. R.; Edwards, J. T.; Qin, T.; Kruszyk, M. M.; Bi, C.; Che, G. D.; Bao, D.-H.; Qiao, W. H.; Sun, L. J.; Collins, M. R.; Fadeyi, O. O.; Gallego, G. M.; Mousseau, J. J.; Nuhant, P.; Baran, P. S. Science 2018, 360, 75. doi: 10.1126/science.aar7335 pmid: 29456201
[8]	Li, J. B.; Zhu, D. H.; Lv, L. Y.; Li, C. J. Chem. Sci. 2018, 9, 5781. doi: 10.1039/C8SC01669K
[9]	Liu, Y.; Xing, S. Y.; Zhang, J.; Liu, W.; Xu, Y. N. A.; Zhang, Y.; Yang, K. F.; Yang, L.; Jiang, K. Z.; Shao, X. X. Org. Chem. Front. 2022, 9, 1375. doi: 10.1039/D1QO01873F
[10]	Cao, L.; Li, J.-X.; Wu, H.-Q.; Jiang, K.; Hao, Z.-F.; Luo, S.-H.; Wang, Z.-Y. ACS Sustainable Chem. Eng. 2018, 6, 4147. doi: 10.1021/acssuschemeng.7b04564
[11]	Yang, K.; Gao, J.-J.; Luo, S.-H.; Wu, H.-Q.; Pang, C.-M.; Wang, B.-W.; Chen, X.-Y.; Wang, Z.-Y. RSC Adv. 2019, 9, 19917. doi: 10.1039/c9ra03403j
[12]	Keshari, T.; Kapoorr, R.; Yadav, L. D. S. Synlett 2016, 27, 1878. doi: 10.1055/s-0035-1562101
[13]	Shyam, P. K.; Kim, Y. K.; Lee, C.; Jang, H.-Y. Adv. Synth. Catal. 2016, 358, 56. doi: 10.1002/adsc.201500785
[14]	Li, X. J.; Zhou, C.; Diao, P. H.; Ge, Y. Q.; Guo, C. Tetrahedron Lett. 2017, 58, 1296. doi: 10.1016/j.tetlet.2017.02.042
[15]	Lv, M. T.; Liu, Y. F.; Li, K.; Yang, G. P. Tetrahedron Lett. 2021, 65, 152757. doi: 10.1016/j.tetlet.2020.152757
[16]	Tranquilino, A.; Andrade, S. R. C. P.; da Silva, A. P. M.; Menezes, P. H.; Oliveira, R. A. Tetrahedron Lett. 2017, 58, 1265
[17]	Zhang, G.-Y.; Lv, S.-S.; Shoberu, A.; Zou, J.-P. J. Org. Chem. 2017, 82, 9801. doi: 10.1021/acs.joc.7b01121
[18]	Kim, J.; Park, S.; Kim, H.; Kim, J. Tetrahedron Lett. 2020, 61, 152112. doi: 10.1016/j.tetlet.2020.152112
[19]	Zhao, X. N.; Liu, T.-X.; Zhang, G. S. Asian J. Org. Chem. 2017, 6, 677. doi: 10.1002/ajoc.201700090
[20]	Liu, L. X.; Luo, B.; Wang, C. M. Eur. J. Org. Chem. 2021, 2021, 5880. doi: 10.1002/ejoc.202101101
[21]	Peng, Z. H.; Zheng, X.; Zhang, Y. J.; An, D. L.; Dong, W. R. Green Chem. 2018, 20, 1760. doi: 10.1039/C8GC00381E
[22]	Kanemoto, K.; Furuhashi, K.; Morita, Y.; Komatsu, T.; Fukuzawa, S. I. Org. Lett. 2021, 23, 1582. doi: 10.1021/acs.orglett.0c04289 pmid: 33513301
[23]	Ji, Y.-Z.; Zhang, C.; Wang, J.-H., Li, H.-J.; Wu, Y.-C. Org. Biomol. Chem. 2021, 19, 9291. doi: 10.1039/D1OB01714D
[24]	Hu, C.; Song, R.-J.; Hu, M.; Yang, Y.; Li, J.-H.; Luo, S. L. Angew. Chem., Int. Ed. 2016, 55, 10423. doi: 10.1002/anie.201604679
[25]	Shi, J.; Tang, X.-D.; Wu, Y.-C.; Fang, J.-F.; Cao, L.; Chen, X.-Y.; Wang, Z.-Y. RSC Adv. 2016, 6, 25651. doi: 10.1039/C6RA01393G
[26]	Shi, J.; Tang, X.-D.; Wu, Y.-C.; Li, H.-N.; Song, L.-J.; Wang, Z.-Y. Eur. J. Org. Chem. 2015, 2015, 1193. doi: 10.1002/ejoc.201403404
[27]	Cao, L.; Luo, S.-H.; Wu, H.-Q.; Chen, L.-Q.; Jiang, K.; Hao, Z.-F.; Wang, Z.-Y. Adv. Synth. Catal. 2017, 359, 2961. doi: 10.1002/adsc.201700600
[28]	Cao, L.; Luo, S.-H.; Jiang, K.; Hao, Z.-F.; Wang, B.-W.; Pang, C.-M.; Wang, Z.-Y. Org. Lett. 2018, 20, 4754. doi: 10.1021/acs.orglett.8b01808
[29]	Sheng, J.; Li, Y. W.; Qiu, G. Y. S. Org. Chem. Front. 2017, 4, 95. doi: 10.1039/C6QO00530F
[30]	Huang, C.-M.; Li, J.; Wang, S.-Y.; Ji, S.-J. Chin. Chem. Lett. 2020, 31, 1923. doi: 10.1016/j.cclet.2019.12.032
[31]	Li, Y. W.; Qiu, G. Y. S.; Wang, H. L.; Sheng, J. Tetrahedron Lett. 2017, 58, 690. doi: 10.1016/j.tetlet.2017.01.018
[32]	Zheng, Y.; Qing, F.-L.; Huang, Y. G.; Xu, X.-H. Adv. Synth. Catal. 2016, 358, 3477. doi: 10.1002/adsc.201600633
[33]	Sarkar, D.; Ghosh, M. K.; Rout, N. Tetrahedron Lett. 2018, 59, 2360. doi: 10.1016/j.tetlet.2018.05.017
[34]	Zhou, G. D.; Xu, X.-D.; Chen, G.-P.; Wei, W.-T.; Guo, Z.-Y. Synlett 2018, 29, 2076. doi: 10.1055/s-0037-1610649
[35]	Chen, Q.; Huang, Y. L.; Wang, X. F.; Wu, J. W.; Yu, G. D. Org. Biomol. Chem. 2018, 16, 1713. doi: 10.1039/C8OB00244D
[36]	Xu, L.; Xu, P.; Zhu, Y.-M.; Rao, W. D.; Wang, S.-Y. Org. Chem. Front. 2021, 8, 5383. doi: 10.1039/D1QO00972A
[37]	Raghuvanshi, D. S.; Verma, N. A. Org. Biomol. Chem. 2021, 19, 4760. doi: 10.1039/d1ob00036e pmid: 33978047
[38]	Zhang, G. F.; Fan, Q. K.; Zhao, Y. Y.; Wang, H. M.; Ding, C. R. Synlett 2021, 32, 81. doi: 10.1055/s-0040-1707310
[39]	Yang, Z. Z.; Shi, Y. S.; Zhan, Z.; Zhang, H.; Xing, H. M.; Lu, R. X.; Zhang, Y. M.; Guan, M.; Wu, Y. ChemElectroChem 2018, 5, 3619. doi: 10.1002/celc.201801058
[40]	Terent'ev, A. O.; Mulina, O. M.; Ilovaisky, A. I.; Kokorekin, V. A.; Nikishin, G. I. Mendeleev Commun. 2019, 29, 80. doi: 10.1016/j.mencom.2019.01.027
[41]	Mo, Z.-Y.; Swaroop, T. R.; Tong, W.; Zhang, Y.-Z.; Tang, H.-T.; Pan, Y.-M.; Sun, H.-B.; Chen, Z.-F. Green Chem. 2018, 20, 4428. doi: 10.1039/C8GC02143K
[42]	Zhong, Z. J.; Xu, P.; Ma, J. F.; Zhou, A. H. Tetrahedron 2021, 99, 132444. doi: 10.1016/j.tet.2021.132444
[43]	Zhang, X. F.; Cui, T., Zhang, Y. H.; Gu, W. J.; Liu, P.; Sun, P. P. Adv. Synth. Catal. 2019, 361, 2014. doi: 10.1002/adsc.201900047
[44]	Strehl, J.; Hilt, G. Eur. J. Org. Chem. 2022, 2022, e202101007.
[45]	Melchiorre, P. Chem. Rev. 2022, 122, 1483. doi: 10.1021/acs.chemrev.1c00993 pmid: 35078320
[46]	Nair, A. M.; Kumar, S.; Halder, I.; Volla, C. M. R. Org. Biomol. Chem. 2019, 17, 5897. doi: 10.1039/C9OB01040H
[47]	Gong, X. X.; Li, X. F.; Xie, W. L.; Wu, J.; Ye, S. Q. Org. Chem. Front. 2019, 6, 1863. doi: 10.1039/C9QO00410F
[48]	Lv, Y. F.; Luo, J. Y.; Ma, Y. C.; Dong, Q.; He, L. Org. Chem. Front. 2021, 8, 2461. doi: 10.1039/D1QO00112D
[49]	Huang, S.; Wang, H.; Liu, Y. G.; Sun, B. G.; Tian, H. Y.; Liang, S. J. Sulfur Chem. 2021, 42, 604. doi: 10.1080/17415993.2021.1932887
[50]	Feng, C. L.; Wang, J.; Tang, Q. J.; Zhong, Z. J.; Qiao, S. S.; Liu, X. Y.; Chen, C.; Zhou, A. H. Carbohydr. Res. 2019, 471, 1. doi: 10.1016/j.carres.2018.10.005
[51]	Huang, S.; Wang, H.; Liu, Y. G.; Sun, B. G.; Tian, H. Y.; Liang, S. J. Sulfur Chem. 2021, 42, 604. doi: 10.1080/17415993.2021.1932887
[52]	Kalaramna, P.; Goswami, A. Eur. J. Org. Chem. 2021, 2021, 5359. doi: 10.1002/ejoc.202101031
[53]	Li, G. Q.; Gan, Z. Y.; Kong, K. X.; Dou, X. M.; Yang, D. S. Adv. Synth. Catal. 2019, 361, 1808. doi: 10.1002/adsc.201900157
[54]	Zhang, H. W.; Yu, F.; Li, C.; Tian, P. Y.; Zhou, Y. L.; Cao, Z.-Y. Org. Lett. 2021, 23, 4721. doi: 10.1021/acs.orglett.1c01443
[55]	Wu, Z.; Xu, Y. H.; Wu, X. X.; Zhu, C. Tetrahedron 2020, 76, 131692. doi: 10.1016/j.tet.2020.131692
[56]	Zhao, X.; Yang, B.; Wei, A. Q.; Sheng, J. Q.; Tian, M. M.; Li, Q.; Lu, K. Tetrahedron Lett. 2018, 59, 1719.
[57]	Chen, H.; Yan, Y. Y.; Zhang, N. N.; Mo, Z. Y.; Xu, Y. L.; Chen, Y. Y. Org. Lett. 2021, 23, 376. doi: 10.1021/acs.orglett.0c03876 pmid: 33351638
[58]	Dong, Y.; Ji, P.; Zhang, Y. T.; Wang, C. Q.; Meng, X.; Wang, W. Org. Lett. 2020, 22, 9562. doi: 10.1021/acs.orglett.0c03624 pmid: 33300807
[59]	Li, Z.; Wang, K. F.; Zhao, X.; Ti, H. H.; Liu, X.-G.; Wang, H. G. Nat. Commun. 2020, 11, 5036. doi: 10.1038/s41467-020-18834-6
[60]	Ravi, C.; Joshi, A.; Adimurthy, S. Eur. J. Org. Chem. 2017, 2017, 3646. doi: 10.1002/ejoc.201700487
[61]	Li, J.; Wang, S.-Y.; Ji, S.-J. J. Org. Chem. 2019, 84, 16147. doi: 10.1021/acs.joc.9b02431
[62]	Huo, J. P.; Lu, M. X.; Wang, Z. Y.; Li, Y. Z. Chin. J. Chem. 2012, 30, 2411. doi: 10.1002/cjoc.201200638
[63]	Kanemoto, K.; Yoshida, S.; Hosoya, T. Org. Lett. 2019, 21, 3172. doi: 10.1021/acs.orglett.9b00875 pmid: 31002255
[64]	Li, H. Y.; Cheng, Z. R.; Tung, C.-H.; Xu, Z. H. ACS Catal. 2018, 8, 8237. doi: 10.1021/acscatal.8b02194
[65]	Xue, F.-L.; Peng, P.; Shi, J.; Zhong, M.-L.; Wang, Z.-Y. Synth. Commun. 2014, 44, 1944. doi: 10.1080/00397911.2013.879899
[66]	Song, T. T.; Li, H. Y.; Wei, F.; Tung, C.-H.; Xu, Z. H. Tetrahedron Lett. 2019, 60, 916. doi: 10.1016/j.tetlet.2019.02.039
[67]	Peng, Z. Y.; Yin, H. L.; Zhang, H.; Jia, T. Z. Org. Lett. 2020, 22, 5885. doi: 10.1021/acs.orglett.0c01982
[68]	Qi, J. L.; Wei, F.; Huang, S.; Tung, C.-H.; Xu, Z. H. Angew. Chem., Int. Ed. 2021, 60, 4561. doi: 10.1002/anie.202013450
[69]	Yuan, B. X.; Jiang, Y.; Qi, Z. J.; Guan, X.; Wang, T.; Yan, R. L. Adv. Synth. Catal. 2019, 361, 5112. doi: 10.1002/adsc.201900620
[70]	Huo, J.-P.; Deng, G.-H.; Wu, W.; Xiong, J.-F.; Zhong, M.-L.; Wang, Z.-Y. Macromol. Rapid Commun. 2013, 34, 1779. doi: 10.1002/marc.201300637
[71]	Wang, X.-X.; Sun, B.-X.; Zhao, Z.-W.; Chen, X.; Xia, W.-J.; Shen, Y. A.; Li, Y.-M. Adv. Synth. Catal. 2022, 364, 165. doi: 10.1002/adsc.202100938
[72]	Reddy, R. J.; Waheed, M.; Kumari, A. H.; Krishna, G. R. Adv. Synth. Catal. 2022, 364, 319. doi: 10.1002/adsc.202101256
[73]	Wang, W. G.; Huang, S.; Yan, S. K.; Sun, X. J.; Tung, C.-H.; Xu, Z. H. Chin. J. Chem. 2020, 38, 445. doi: 10.1002/cjoc.201900556
[74]	Wang, B.-W.; Jiang, K.; Li, J.-X.; Luo, S.-H.; Wang, Z.-Y.; Jiang, H.-F. Angew. Chem., Int. Ed. 2020, 59, 2338. doi: 10.1002/anie.201914333
[75]	Reddy, R. J.; Kumar, J. J.; Kumari, A. H. Eur. J. Org. Chem. 2019, 2019, 3771. doi: 10.1002/ejoc.201900676
[76]	Cao, L. D.; Jimeno, C.; Renaud, P. Adv. Synth. Catal. 2020, 362, 3644. doi: 10.1002/adsc.202000657
[77]	Zhang, D.-R.; Hu, L.-P.; Yang, C.-Y.; Li, X.; Teng, M.-Y.; Liu, B.; Huang, G.-L. Asian J. Org. Chem. 2022, 11, e202100694.
[78]	Son, S.; Shyam, P. K.; Park, H.; Jeong, I.; Jang, H.-Y. Eur. J. Org. Chem. 2018, 2018, 3365. doi: 10.1002/ejoc.201800778
[79]	Mao, K. M.; Bian, M. W.; Dai, L.; Zhang, J. H.; Yu, Q. Y.; Wang, C.; Rong, L. L. Org. Lett. 2021, 23, 218. doi: 10.1021/acs.orglett.0c03946
[80]	Liang, Q. J.; Walsh, P. J.; Jia, T. Z. ACS Catal. 2020, 10, 2633. doi: 10.1021/acscatal.9b04887
[81]	Huang, S.; Li, H. Y.; Xie, T.; Wei, F.; Tung, C.-H.; Xu, Z. H. Org. Chem. Front. 2019, 6, 1663. doi: 10.1039/C9QO00138G
[82]	Liu, Y.; Zhang, N. N.; Xu, Y. Y.; Chen, Y. Y. J. Org. Chem. 2021, 86, 16882. doi: 10.1021/acs.joc.1c02082
[83]	Liu, X.-Y.; Tian, S.-Y.; Jiang, Y.-F.; Rao, W. D.; Wang, S.-Y. Org. Lett. 2021, 23, 8246. doi: 10.1021/acs.orglett.1c02981
[84]	Huang, S.; Thirupathi, N.; Tung, C.-H.; Xu, Z. H. J. Org. Chem. 2018, 83, 9449. doi: 10.1021/acs.joc.8b01161
[85]	Gadde, K.; Mampuys, P.; Guidetti, A.; Ching, H. Y. V.; Herrebout, W. A.; Van Doorslaer, S.; Tehrani, K. A.; Maes, B. U. W. ACS Catal. 2020, 10, 8765. doi: 10.1021/acscatal.0c02159
[86]	Zhou, X.; Peng, Z. Y.; Wang, P. G.; Liu, Q. C.; Jia, T. Z. Org. Lett. 2021, 23, 1054. doi: 10.1021/acs.orglett.0c04254 pmid: 33428413
[87]	Shankar, A.; Waheed, M.; Reddy, R. J. SynOpen 2021, 5, 91. doi: 10.1055/a-1422-9411
[88]	Fang, Y., Rogge, T., Ackermann, L., Wang, S.-Y.; Ji, S.-J. Nat. Commun. 2018, 9, 2240. doi: 10.1038/s41467-018-04646-2 pmid: 29884782
[89]	Ang, N. W. J.; Ackermann, L. Chem.-Eur. J. 2021, 27, 4883. doi: 10.1002/chem.202005449
[90]	Kumari, A. H.; Kumar, J. J.; Krishna, G. R.; Reddy, R. J. Synthesis 2021, 53, 2850. doi: 10.1055/a-1482-2486
[91]	Reddy, R. J.; Kumari, A. H.; Kumar, J. J.; Nanubolu, J. B. Adv. Synth. Catal. 2019, 361, 1587. doi: 10.1002/adsc.201801620
[92]	Li, J.; Rao, W. D.; Wang, S.-Y.; Ji, S.-J. J. Org. Chem. 2019, 84, 11542. doi: 10.1021/acs.joc.9b01387
[93]	Yang, K.; Chen, Z.-X.; Zhou, Y.-J.; Chen, Q., Yu, S.-W.; Luo, S.-H.; Wang, Z.-Y. Org. Chem. Front. 2022, 9, 1127. doi: 10.1039/D1QO01753E
[94]	Wang, D. G.; He, Q.; Shi, K. Q.; Xiong, M. T.; Zhou, Y. F.; Pan, Y. J. Adv. Synth. Catal. 2021, 363, 2767. doi: 10.1002/adsc.202100165
[95]	Cai, W. Q.; Gu, Z. H. Org. Lett. 2019, 21, 3204. doi: 10.1021/acs.orglett.9b00923
[96]	Rao, C. Q.; Mai, S. Y.; Song, Q. L. Chem. Commun. 2018, 54, 5964. doi: 10.1039/C8CC01656A
[97]	Yuan, H. R.; Nuligonda, T.; Gao, H. Y.; Tung, C.-H.; Xu, Z. H. Org. Chem. Front. 2018, 5, 1371. doi: 10.1039/C7QO01131H
[98]	Zhao, X.; Zheng, X. C.; Tian, M. M.; Tong, Y. F.; Yang, B.; Wei, X. F.; Qiu, D.; Lu, K. Org. Chem. Front. 2018, 5, 2636. doi: 10.1039/C8QO00401C
[99]	Wang, W. G.; Zhang, S. X.; Zhao, H. Q.; Wang, S. F. Org. Biomol. Chem. 2018, 16, 8565. doi: 10.1039/C8OB02431F
[100]	Huang, C. M.; Li, J.; Ai, J. J.; Liu, X. Y.; Rao, W. D.; Wang, S.-Y. Org. Lett. 2020, 22, 9128. doi: 10.1021/acs.orglett.0c03562
[101]	Li, A. K.; Li, Y. X.; Liu, J. J.; Chen, J. Q.; Lu, K.; Qiu, D.; Fagnoni, M.; Protti, S.; Zhao, X. J. Org. Chem. 2021, 86, 1292. doi: 10.1021/acs.joc.0c02669
[102]	Shyam, P. K.; Jang, H. Y. J. Org. Chem. 2017, 82, 1761. doi: 10.1021/acs.joc.6b03016
[103]	Tong, J. W.; Li, H.; Zhu, Y.; Liu, P.; Sun, P. P. Green Chem. 2022, 24, 1995. doi: 10.1039/D1GC04703E
[104]	Bi, W.-Z.; Zhang, W.-J.; Li, Z.-J.; He, Y.-H.; Feng, S.-X.; Geng, Y.; Chen, X.-L.; Qu, L.-B. Org. Biomol. Chem. 2021, 19, 8701. doi: 10.1039/D1OB01592C
[105]	Wei, L. D.; Wu, C. J.; Tung, C.-H., Wang, W. G.; Xu, Z. H. Org. Chem. Front. 2019, 6, 3224. doi: 10.1039/C9QO00817A
[106]	Chen, Y.; Wang, F.; Liu, B.-X.; Rao, W.-D. Wang, S.-Y. Org. Chem. Front. 2022, 9, 731. doi: 10.1039/D1QO01614H
[107]	Zhang, Y. T.; Ji, P.; Hu, W. B.; Wei, Y. Y.; Huang, H.; Wang, W. Chem. Eur. J. 2019, 25, 8225. doi: 10.1002/chem.201900932
[108]	Guo, S.-H.; Zhang, X.-L.; Pan, G.-F.; Zhu, X.-Q.; Gao, Y.-R.; Wang, Y.-Q. Angew. Chem., Int. Ed. 2018, 57, 1663. doi: 10.1002/anie.201710731
[109]	Guo, S.-H.; Wang, M.-Y.; Pan, G.-F.; Zhu, X.-Q.; Gao, Y.-R.; Wang, Y.-Q. Adv. Synth. Catal. 2018, 360, 1861. doi: 10.1002/adsc.201800136
[110]	Xu, B.; Li, D. Z.; Lu, L.; Wang, D. C.; Hu, Y. H.; Shen, Q. L. Org. Chem. Front. 2018, 5, 2163. doi: 10.1039/C8QO00327K
[111]	Yan, J. M; Tang, H. D.; Kuek, E. J. R.; Shi, X. C.; Liu, C. G.; Zhang, M. L.; Piper, J. L.; Duan, S. Q.; Wu, J. Nat. Commun. 2021, 12, 7214. doi: 10.1038/s41467-021-27550-8
[112]	Bizzini, L. D.; Zwick, P.; Mayor, M. Eur. J. Org. Chem. 2019, 2019, 6956. doi: 10.1002/ejoc.201901283
[113]	Reddy, R. J.; Waheed, M.; Kumar, J. J. RSC Adv. 2018, 8, 40446. doi: 10.1039/C8RA06938G
[114]	Reddy, R. J.; Waheed, M.; Krishna, G. R. Org. Biomol. Chem. 2020, 18, 3243. doi: 10.1039/D0OB00442A
[115]	Wang, F.; Wang, S.-Y. Org. Chem. Front. 2021, 8, 1976. doi: 10.1039/D1QO00085C
[116]	Kanemoto, K.; Sakata, Y.; Hosoya, T.; Yoshida, S. Chem. Lett. 2020, 49, 593. doi: 10.1246/cl.200132
[117]	Luo, Z. W.; Yang, X. K.; Tsui, G. C. Org. Lett. 2020, 22, 6155. doi: 10.1021/acs.orglett.0c02235
[118]	Luo, J. Y.; Lin, M. Z.; Wu, L. F.; Cai, Z. H.; He, L.; Du, G. F. Org. Biomol. Chem. 2021, 19, 9237. doi: 10.1039/D1OB01350E

硫代磺酸酯的合成与应用研究进展

Research Progress in Synthesis and Application of Thiosulfonates

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 8

References 118

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jing Huang, Yihua Yang, Zhanhui Zhang, Shouxin Liu. Recent Progress on Green Methods and Technologies for Efficient Formation of Amide Bonds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 409-420.
[2]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[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]	Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84.
[5]	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.
[6]	Yixin Jiang, Boxiao Tang, Haibo Mao, Xuexia Chen, Yangjie Yu, Cuiying Quan, Zhaoyang Xu, Jinhui Shi, Yilin Liu. A Green, Recyclable and Carrier-Free Study for the Coupling Reaction of Alkenes with Aryl Iodides in H₂O-Polyethylene Glycol (PEG-200) [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3210-3215.
[7]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[8]	Yingjie Liu, Gangqing Shi, Ge Chou, Xin Zhang, Dongxue Song, Ning Chen, Miao Yu, Ying Xu. Progress of α-Position Functionalization of Ethers under Photo/Electrocatalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2664-2681.
[9]	Lingna Wang, Xiaoqing Liu, Gang Lin, Hongying Jin, Minjun Jiao, Xuefen Liu, Shuping Luo. Photocatalytic Activation of C(sp³)—H Bonds to Form C—S Bonds Catalyzed by (Oxybis(4,1-phenylene))bis(phenylmethanone) [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2848-2854.
[10]	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.
[11]	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.
[12]	Jiaxia Pu, Xiaoying Jia, Lirong Han, Qinghan Li. Research Progress of Visible Light Promoted C—N Bond Fracture to Construct C—C Bond [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2591-2613.
[13]	Yaxin Liu, Yu Zhang, Shuping Luo. Design and Synthesis of Thermal Delayed Fluorescence (TADF) Photocatalyst and Its Photocatalytic Dehalogenation Performance [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2476-2483.
[14]	Ning Chen, Chengdong Zhang, Peng Li, Ge Qiu, Yinjie Liu, Tianlei Zhang. Research Progress in Synthesis of Spirocyclic Compounds Driven by Photo/Electrochemistry [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2293-2303.
[15]	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.