直接二氟甲硫基化与一氟甲硫基化反应研究进展

doi:10.6023/cjoc201907028

有机化学 ›› 2020, Vol. 40 ›› Issue (1): 1-14.DOI: 10.6023/cjoc201907028 上一篇下一篇

综述与进展

直接二氟甲硫基化与一氟甲硫基化反应研究进展

闫强, 蒋绿齐, 易文斌

南京理工大学化工学院南京 210094

收稿日期:2019-07-20 修回日期:2019-08-29 发布日期:2019-09-12
通讯作者: 蒋绿齐, 易文斌 E-mail:lvqi.jiang@njust.edu.cn;yiwb@njust.edu.cn
基金资助:
国家自然科学基金（No.21476116）、中央高校基本科研业务费专项资金（No.30918011314）、江苏省自然科学基金（No.BK20141394）和江苏省青蓝计划和六大高峰人才资助项目.

Recent Progress on Direct Difluoromethylthiolation and Monofluoromethylthiolation

Yan Qiang, Jiang Lüqi, Yi Wenbin

Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094

Received:2019-07-20 Revised:2019-08-29 Published:2019-09-12
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21476116), the Fundamental Research Funds for the Central Universities (No. 30918011314), the Natural Science Foundation of Jiangsu Province (No. BK20141394) and the Qing Lan and Six Talent Peaks in Jiangsu Province.

文章分享

摘要/Abstract

含有二氟甲硫基基团（SCF₂H）与含有一氟甲硫基基团（SCFH₂）的有机化合物具有独特的物理和化学性质，在医药及农药等领域具有潜在的应用价值.这两类化合物的传统制备方法是巯基底物的二氟甲基化与一氟甲基化，但含巯基底物本身种类有限，极大地限制了该类化合物的应用与开发，因此开发新的直接二氟/一氟甲硫基化方法和开拓新型直接二氟/一氟甲硫基化试剂具有重要的意义.综述了直接二氟甲硫基化反应和一氟甲硫基化反应的最新研究进展，并对反应的相关机理进行了论述.

关键词: 二氟甲硫基化, 一氟甲硫基化, 直接法

Compounds bearing difluoromethylthio (SCF₂H) and monofluoromethylthio (SCFH₂) groups are potentially important targets in the pharmaceutical and agrochemical fields due to their unique physical and chemical properties. The traditional methods of synthesizing these two kinds of compounds are difluoromethylation and monofluoromethylation of sulfhydryl substrates. However, the limitation of sulfhydryl substrates also limited the application and development of such compounds. Thus, it is still highly desirable to develop new methods for difluoromethylthiolation and monofluoromethylthiolation as well as new types of difluoromethylthiolation and monofluoromethylthiolation reagents. The recent development of direct difluoromethylthiolation and monofluoromethylthiolation reactions is summarized, and the related mechanism are also discussed.

Key words: difluoromethylthiolation, monofluoromethylthiolation, direct method

引用此文

闫强, 蒋绿齐, 易文斌. 直接二氟甲硫基化与一氟甲硫基化反应研究进展[J]. 有机化学, 2020, 40(1): 1-14.

Yan Qiang, Jiang Lüqi, Yi Wenbin. Recent Progress on Direct Difluoromethylthiolation and Monofluoromethylthiolation[J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 1-14.

导出引用 EndNote|Reference Manager|ProCite|BibTeX|RefWorks

分享此文

参考文献

[1] Erickson, J. A.; McLoughlin, J. I. J. Org. Chem. 1995, 60, 1626
[2] Bayarmagnai, B.; Matheis, C.; Jouvin, K.; Goossen, L. J. Angew. Chem., Int. Ed. 2015, 54, 5753
[3] Fourie, J. J.; Horak, I. G.; Redondo, P. V. Vet. Rec. 2010, 167, 442
[4] Morita, K.; Ide, K.; Hayase, Y.; Takahashi, T.; Hayashi, Y. Agric. Biol. Chem. 1987, 51, 1339.
[5] Yagupolskii, L. M.; Maletina, I. I.; Petko, K. I.; Fedyuk, D. V.; Handrock, R.; Shavaran, S. S.; Klebanov, B. M.; Herzig, S. J. Fluorine Chem. 2001, 109, 87.
[6] Shimizu, K. Jpn. J. Antibiot. 1988, 12, 1809
[7] Kettner, M.; Krčmery, V.; Bonini, P.; Cichero, P.; Ossi, C.; Grazioli, V. Infection 1991, 19, 253
[8] Burkholder, C. R.; Dolbier, W. R.; Medebielle, M. J. Fluorine Chem. 2000, 102, 369
[9] Boiko, V. N. Beilstein J. Org. Chem. 2010, 6, 880
[10] 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.
[11] Howland, W. C. Clin. Exp. Allergy 1996, 26, 18.
[12] Jung, M.; Wahl, A. F.; Neupert, W.; Geisslinger, G.; Senter, P. D. Pharm. Pharmacol. Commun. 2000, 6, 217.
[13] Hine, J.; Porter, J. J. J. Am. Chem. Soc. 1957, 79, 5493.
[14] Prakash, G. K. S.; Ni, C. F.; Wang, F.; Hu, J. B.; Olah, G. A. Angew. Chem., Int. Ed. 2011, 50, 2559.
[15] Zhao, Y. C.; Huang, W. Z.; Zhu, L. G.; Hu, J. B. Org. Lett. 2010, 12, 1444.
[16] Kudo, N.; Yondea, A.; Sato, K.; Honma, T.; Sugai, S. Chem. Pharm. Bull. 2000, 48, 509.
[17] Wang, W. Q.; Yu, Q. W.; Zhang, Q.; Li, J. W.; Hui, F.; Yang, J. M.; Lü, J. Chin. J. Org. Chem. 2018, 38, 1569(in Chinese). (王为强, 余秦伟, 张前, 李江伟, 惠丰, 杨建明, 吕剑, 有机化学, 2018, 38, 1569.)
[18] Fuchibe, K.; Bando, M.; Takayama, R.; Ichikawa, J. J. Fluorine Chem. 2015, 171, 133.
[19] Zafrani, Y.; Sod-Moriah, G.; Segall, Y. Tetrahedron 2009, 65, 5278.
[20] Zhang, W.; Wang, F.; Hu, J. B. Org. Lett. 2009, 11, 2109.
[21] Wang, F.; Huang, W. Z.; Hu, J. B. Chin. J. Chem. 2011, 29, 2717.
[22] Prakash, G. K. S.; Zhang, Z.; Wang, F.; Ni, C. F.; Olah, G. A. J. Fluorine Chem. 2011, 132, 792.
[23] Fier, P. S.; Hartwig, J. F. Angew. Chem., Int. Ed. 2013, 52, 2092.
[24] Li, L. C.; Wang, F.; Ni, C. F.; Hu, J. B. Angew. Chem., Int. Ed. 2013, 52, 12390.
[25] Han, J. B.; Qin, H. L.; Ye, S. H.; Zhu, L; Zhang, C. P. J. Org. Chem. 2016, 81, 2506.
[26] Howard, J. L.; Schotten, C.; Alston, S. T.; Browne, D. L. Chem. Commun. 2016, 52, 8448.
[27] Thomoson, C. S.; Dolbier, Jr. W. R. J. Org. Chem. 2013, 78, 8904.
[28] Mehta, V. P.; Greaney, M. F. Org. Lett. 2013, 15, 5036.
[29] Deng, X. Y.; Lin, J. H.; Zheng, J.; Xiao, J. C. Chem. Commun. 2015, 51, 8805.
[30] Fujiwara, Y.; Dixon, J. A.; Rodrigue, R. A.; Baxter, R. D.; Dixon, D. D.; Collins, M. R.; Blackmond, D. G.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 1494.
[31] Lin, Y. M.; Yi, W. B.; Shen, W. Z; Lu, G. P. Org. Lett. 2016, 18, 592.
[32] Zhu, D. H.; Gu, Y.; Lu, L.; Shen, Q. L. J. Am. Chem. Soc. 2015, 137, 10547.
[33] Zhu, D. H.; Hong, X.; Li, D. Z.; Lu, L.; Shen, Q. L. Org. Process Res. Dev. 2017, 21, 1383.
[34] Yang, Y. D.; Azuma, A.; Tokunaga, E.; Yamasaki, M.; Shiro, M.; Shibata, N. J. Am. Chem. Soc. 2013, 135, 8782.
[35] Arimori, S.; Matsubara, O.; Takada, M.; Shibata, N. R. Soc. Open Sci. 2016, 3, 1601021.
[36] Gondo, S.; Matsubara, O.; Chachignon, H.; Sumii, Y.; Cahard, D.; Shibata, N. Molecules 2019, 24, 221.
[37] Jiang, L. Q.; Yi, W. B.; Liu, Q. R. Adv. Synth. Catal. 2016, 358, 3700.
[38] Zhao, X.; Wei, A. Q.; Li, T. J.; Su, Z. Y.; Chen, J.; Lu, K. Org. Chem. Front. 2017, 4, 232.
[39] Zhao, X.; Li, T. J.; Yang, B.; Qiu, D.; Lu, K. Tetrahedron 2017, 73, 3112.
[40] Jiang, L. Q.; Ding, T. Q.; Yi, W. B.; Zhang, W. Org. Lett. 2018, 20, 2236.
[41] Jiang, L. Q.; Yan, Q.; Wang, R. K.; Ding, T. Q.; Yi, W. B.; Zhang, W. Chem.-Eur. J. 2018, 24, 18749.
[42] Yan, Q.; Jiang, L. Q.; Yi, W. B.; Liu, Q. R.; Zhang, W. Adv. Synth. Catal. 2017, 359, 2471.
[43] Huang, Z. Y.; Matsubara, O.; Jia, S. C.; Tokunag, E.; Shibata, N. Org. Lett. 2017, 19, 934.
[44] Zhang, P. P.; Lü, L.; Shen, Q. L. Acta Chim. Sinica 2017, 75, 744(in Chinese). (张盼盼, 吕龙, 沈其龙, 化学学报, 2017, 75, 744.)
[45] Hu, J. J.; Huang, Y. G.; Xu, X. H.; Qing, F. L. Chin. J. Org. Chem. 2018, 38, 177(in Chinese). (胡娟娟, 黄焰根, 徐修华, 卿凤翎, 有机化学, 2018, 38, 177.)
[46] Wu, J.; Gu, Y.; Leng, X. B.; Shen, Q. L. Angew. Chem., Int. Ed. 2015, 54, 7648.
[47] Wu, J.; Liu, Y. F.; Lu, C. H.; Shen, Q. L. Chem. Sci. 2016, 7, 3757.
[48] Wu, J.; Lu, C. H.; Lu, L.; Shen, Q. L. Chin. J. Chem. 2018, 36, 1031.
[49] Zhu, D. H.; Shao, X. X.; Hong, X.; Lu, L.; Shen, Q. L. Angew. Chem., Int. Ed. 2016, 55, 15807.
[50] Xu, B.; Wang, D. C.; Hu, Y. H.; Shen, Q. L. Org. Chem. Front. 2018, 5, 1462.
[51] Li, J. B.; Zhu, D. H.; Lv, L. Y.; Li, C. J. Chem. Sci. 2018, 9, 5781.
[52] 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.
[53] Li, H. Y.; Cheng, Z. R.; Tung, C. H.; Xu, Z. H. ACS Catal. 2018, 8, 8237.
[54] Xuan, J.; Zhang, Z. G.; Xiao, W. J. Angew. Chem., Int. Ed. 2015, 54, 15632.
[55] Prier, C. K.; Rankic, D. A.; MacMillan, W. C. Chem. Rev. 2013, 113, 5322.
[56] Candish, L.; Pitzer, L.; Gomez, S. A.; Glorius. F. Chem.-Eur. J. 2016, 22, 4753.
[57] Xu, W. T.; Ma, J. Y.; Yuan, X. A.; Dai, J.; Xie, J.; Zhu, C. J. Angew. Chem., Int. Ed. 2018, 57, 10357.
[58] Jouvin, K.; Matheis, C.; Goossen, L. J. Chem.-Eur. J. 2015, 21, 14324.
[59] Ding, T. Q.; Jiang, L. Q.; Yi, W. B. Org. Lett. 2018, 20, 170.
[60] Yu, J.; Lin, J. H.; Xiao, J. C. Angew. Chem., Int. Ed. 2017, 56, 16669.
[61] Yang, O.; Gooßen, L. J. Asian J. Org. Chem. 2018, 8, 650.
[62] Xu, L. J.; Wang, H. Y.; Zheng, C. W.; Zhao, G. Tetrahedron 2017, 73, 6057.
[63] Shen, F.; Zhang, P. P.; Lu, L.; Shen, Q. L. Org. Lett. 2017, 19, 1032.
[64] Ismalaj, E.; Bars, D. L.; Billard T. Angew. Chem., Int. Ed. 2016, 55, 4790.
[65] Ismalaj, E.; Billard, T. J. Fluorine Chem. 2017, 203, 215.
[66] Ismalaj, E.; Glenadel, Q.; Billard T. Eur. J. Org. Chem. 2017, 14, 1911.
[67] Xiong, H. Y.; Bayle, A.; Pannecoucke, X.; Besset, T. Angew. Chem., Int. Ed. 2016, 55, 13490.
[68] Robins, M. J.; Wnuk, S. F. J. Org. Chem. 1993, 58, 3800.
[69] Shinichi, A.; Norihiko, Y.; Tsuyoshi, F.; Shoji, H. Bull. Chem. Soc. Jpn. 2002, 75, 1597.
[70] Lal, G. S.; Pez, G. P.; Pesaresi, R. J.; Prozonic, F. M.; Cheng, H. J. Org. Chem. 1999, 64, 7048.
[71] Matthews, D. P.; Persichetti, R. A.; McCarthy, J. R. Org. Prep. Proced. Int. 1994, 26, 605.
[72] Phillipps, G. H.; Bailey, E. J.; Bain, B. M.; Borella. R. A.; Buckton, J. B.; Clark, J. C.; Doherty, A. E.; English, A. F.; Fazakerley, H.; Laing, S. B.; Allman, E. L.; Robinson, J. D.; Sandford, P. E.; Sharratt, P. J.; Steeples, I. P.; Stonehouse, R. D.; Williamson, C. J. Med. Chem. 1994, 37, 3717.
[73] Aigbirhio, F. I.; Carr, R. M.; Pike, V. W.; Steel, C. J.; Sutherland, D. R. J. Labelled Compd. Radiopharm. 1997, 39, 567.
[74] Tanigawa, M.; Kuriyama, Y.; Inagi, S.; Fuchigami, T. Electrochim. Acta 2016, 199, 314.
[75] Boys, M. L.; Collington, E. W.; Finch, H.; Swanson, S.; Whitehead, J. F. Tetrahedron Lett. 1988, 29, 3365.
[76] McCarthy, J. R.; Peet, N. P.; LeTourneau, M. E.; Inbasekaran, M. J. Am. Chem. Soc. 1985, 107, 735.
[77] 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.
[78] Biggadike, K.; Bledsoe, R. K.; Hassell, A. M.; Kirk, B. E.; McLay, I. M.; Shewchuk, L. M.; Stewart, E. L. J. Med. Chem. 2008, 51, 3349.
[79] Zhang, W.; Zhu, L. G.; Hu, J. B. Tetrahedron 2007, 63, 10569.
[80] Prakash, G. K. S.; Ledneczki, I.; Chacko, S.; Olah, G. A. Org. Lett. 2008, 10, 557.
[81] Zhang, M. R.; Ogawa, M.; Furutsuka, K.; Yoshida, Y.; Suzuki, K. J. Fluorine Chem. 2004, 125, 1879.
[82] Boddy, I. K.; Briggs, G. G.; Harrison, R. P.; Jones, T. H.; O'Mahony, M. J.; Marlow, I. D.; Roberts, B. G.; Willis, R. J.; Bardsley, R.; Reid, R. Pestic. Sci. 1996, 48, 189.
[83] Machara, N. P.; Ault, B. S. J. Mol. Struct. 1988, 172, 129.
[84] Zhao, Q. C.; Lu, L.; Shen, Q. L. Angew. Chem., Int. Ed. 2017, 56, 11575.
[85] Guo, S. H.; Wang, M. Y.; Pan, G. F.; Zhu, X. Q.; Gao, Y. R.; Wang, Y. Q. Adv. Synth. Catal. 2018, 360, 1861.
[86] Liu, F. M.; Jiang, L. Q.; Qiu, H. Y.; Yi, W. B. Org. Lett. 2018, 20, 6270.

直接二氟甲硫基化与一氟甲硫基化反应研究进展

Recent Progress on Direct Difluoromethylthiolation and Monofluoromethylthiolation

PDF

可视化

摘要/Abstract

引用此文

分享此文

参考文献

相关文章 0

编辑推荐

相关统计

本文评价