Progress on the Synthesis and Applications of Thiocyanates

doi:10.6023/cjoc201807016

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (2): 287-300.DOI: 10.6023/cjoc201807016 Previous Articles Next Articles

REVIEW

硫氰酸酯类化合物的合成及其应用研究进展

徐庆^a, 张连阳^b, 冯高峰^a, 金城安^a

a 绍兴文理学院化学化工学院绍兴 312000;
b 绍兴文理学院纺织服装学院绍兴 312000

收稿日期:2018-07-08 修回日期:2018-08-27 发布日期:2018-09-18
通讯作者: 金城安 E-mail:jca@usx.edu.cn
基金资助:
绍兴文理学院校级科研（No.2017LG1001）资助项目.

Progress on the Synthesis and Applications of Thiocyanates

Xu Qing^a, Zhang Lianyang^b, Feng Gaofeng^a, Jin Chengan^a

a College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing 312000;
b College of Textile and Garment, Shaoxing University, Shaoxing 312000

Received:2018-07-08 Revised:2018-08-27 Published:2018-09-18
Contact: 10.6023/cjoc201807016 E-mail:jca@usx.edu.cn
Supported by:
Project supported by the Research Project of Shaoxing University (No. 2017LG1001).

Thiocyanates (RSCN) are important synthetic intermediates, which have been widely used for the synthesis of pesticides, medicines and materials. In recent years, great advances in the synthesis and transformations of this class of compounds have been made, and many synthetic applications of those compounds have been emerged. In this review, the synthetic methods and transformations of thiocyanates are introduced systematically, which may provide assistance for the studies of thiocyanates in this area.

Key words: thiocyanates, synthetic methods, application

Cite this article

Xu Qing, Zhang Lianyang, Feng Gaofeng, Jin Chengan. Progress on the Synthesis and Applications of Thiocyanates[J]. Chin. J. Org. Chem., 2019, 39(2): 287-300.

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References

[1] Elhalem, E.; Bailey, B. N.; Docampo, R.; Ujvary, I.; Szajnman, S. H.; Rodriguez, J. B. J. Med. Chem. 2002, 45, 3984.
[2] Kokorekin, V. A.; Terent'ev, A. O.; Ramenskaya, G. V.; Gram-matikova, N. E.; Rodionava, G. M.; llovaiskii, A. I. Pharm. Chem. J. 2013, 47, 422.
[3] Dutta, S.; Abe, H.; Aoyagi, S.; Kibayashi, C.; Gates, K. S. J. Am. Chem. Soc. 2005, 127, 15004.
[4] Capon, R. J.; Skene, C.; Liu, E. H.-T.; Lacey, E.; Gill, J. H.; Heiland, K.; Friedel, T. J. Org. Chem. 2001, 66, 7765.
[5] Yasmana, Y.; Edrada, R. A.; Wray, V.; Proksch, P. J. Nat. Prod. 2003, 66, 1512.
[6] Billard, T.; Large, S.; Langlois, B. R. Tetrahedron Lett. 1997, 38, 65.
[7] Johnson, T. B.; Douglass, I. B. J. Am. Chem. Soc. 1939, 61, 2548.
[8] Sabacky, M. J.; Johnson, S. M.; Martin, J. C.; Paul, I. C. J. Am. Chem. Soc. 1969, 91, 7542.
[9] Aureggi, V.; Sedelmeier, G. Angew. Chem. Int. Ed. 2007, 46, 8440.
[10] Ciszek, J. W.; Stewart, M. P.; Tour, J. M. J. Am. Chem. Soc. 2004, 126, 13172.
[11] Still, I. W. J.; Toste, F. D. J. Org. Chem. 1996, 61, 7677.
[12] Castanheiro, T.; Suffert, J.; Donnard, M.; Gulea, M. Chem. Soc. Rev. 2016, 45, 494.
[13] Sun, N.; Che, L.-S.; Mo, W.-M.; Hu, B.-X.; Shen, Z.-L.; Hu, X.-Q. Org. Biomol. Chem. 2015, 13, 691.
[14] Zhu, N.; Wang, F.; Chen, P.-H.; Ye, J.-X.; Liu, G.-S. Org. Lett. 2015, 17, 3580.
[15] Jiang, H.-F.; Yu, W.-T.; Tang, X.-D.; Li, J.-X.; Wu, W.-Q. J. Org. Chem. 2017, 82, 9312.
[16] Chen, Y.-T.; Wang, S.-F.; Jiang, Q.-W.; Cheng, C.-G.; Xiao, X.-H.; Zhu, G.-G. J. Org. Chem. 2018, 83, 716.
[17] Rad, M. N. S. J. Chem. Res. 2016, 40, 583.
[18] Dwivedi, V.; Rajesh, M.; Kumar, R.; Kantc, R.; Reddy, M. S. Chem. Commun. 2017, 53, 11060.
[19] Palsuledesai, C. C.; Murru, S.; Sahoo, S. K.; Patel, B. K. Org. Lett. 2009, 11, 3382.
[20] Modi, A.; Ali, W.; Patel, B. K. Org. Lett. 2017, 19, 432.
[21] Yadav, A. K.; Yadav, L. D. S. Tetrahedron Lett. 2015, 56, 6696.
[22] Zhang, D.; Wang, H.; Bolm, C. Chem. Commun. 2018, 54, 5772.
[23] Liang, S.; Zeng, C.-C.; Tian, H.-Y.; Sun, B.-G.; Luo, X.-G.; Ren, F.-Z. Adv. Synth. Catal. 2018, 360, 1444.
[24] Xiong, H.-Y.; Pannecoucke, X.; Besset, T. Org. Chem. Front. 2016, 3, 620.
[25] Zhang, H.-L.; Wei, Q.; Wei, S.-Q.; Qu, J.-P.; Wang, B.-M. Eur. J. Org. Chem. 2016, 20, 3373.
[26] Chen, Q.; Lei, Y.-J.; Wang, Y.-F.; Wang, C.; Wang, Y.-N.; Xu, Z.-Q.; Wang, H.; Wang, R. Org. Chem. Front. 2017, 4, 369.
[27] Wang, Z.-H.; Wang, L.; Chen, Q.; He, M.-Y. Synth. Commun. 2018, 40, 76.
[28] Venkanna, P.; Rajanna, K. C.; Kumar, M. S.; Venkateswarlu, M.; Ali, M. M. Synlett 2016, 27, 237.
[29] Qiu, J.-S.; Wu, D.; Karmaker, P. G.; Yin, H.-Q.; Chen, F.-X. Org. Lett. 2018, 20, 1600.
[30] Wu, D.; Qiu, J.-S.; Karmaker, P. G.; Yin, H.-Q.; Chen, F.-X. J. Org. Chem. 2018, 83, 1576.
[31] Yang, H.; Duan, X.-H.; Zhao, J.-F.; Guo, L.-N. Org. Lett. 2015, 17, 1998.
[32] Yang, D.-S.; Yan, K.-L.; Wei, W.; Li, G.-Q.; Lu, S.-L.; Zhao, C.-X.; Tian, L.-J.; Wang, H. J. Org. Chem. 2015, 80, 11073.
[33] Zhang, X.-Z.; Ge, D.-L.; Chen, S.-Y.; Yu, X.-Q. RSC Adv. 2016, 6, 66320.
[34] Guo, L.-N.; Gu, Y.-R.; Yang, H.; Hu, J. Org. Biomol. Chem. 2016, 14, 3098.
[35] Chen, J.-C.; Wang, T.-Y.; Wang, T.; Lin, A.-J.; Yao, H.-Q.; Xu, J.-Y. Org. Chem. Front. 2017, 4, 130.
[36] Mete, T. B.; Khopade, T. M.; Bhat, R. G. Tetrahedron Lett. 2017, 58, 415.
[37] Ji, F.; Fan, Y.; Yang, R.; Yang, Y.-Y.; Yu, D.-W.; Wang, M.-Y.; Li, Z.-Y. Asian J. Org. Chem. 2017, 6, 682.
[38] Karmaker, P. G.; Qiu, J.; Wu, D.; Yin, H.; Chen, F. X. Synlett 2018, 29, 954.
[39] Zeng, Y.-F.; Tan, D.-H.; Chen, Y.-Y.; Lv, W.-X.; Liu, X.-G.; Li, Q.-J.; Wang, H.-G. Org. Chem. Front. 2015, 2, 1511.
[40] Lv, Y.-H.; Pu, W.-Y.; Cui, H.; He, J.-L.; Zhang, Q.-M. Synth. Commun. 2016, 46, 1223.
[41] Tao, Z.-K.; Li, C.-K.; Zhang, P.-Z.; Shoberu, A.; Zou, J.-P.; Zhang, W. J. Org. Chem. 2018, 83, 2418.
[42] Fan, W.-G.; Yang, Q.; Xu, F.-S.; Li, P.-X. J. Org. Chem. 2014, 79, 10588.
[43] Mitra, S.; Ghosh, M.; Mishra, S.; Hajra, A. J. Org. Chem. 2015, 80, 8275.
[44] Wang, L.; Wang, C.-C.; Liu, W.-J.; Chen, Q.; He, M.-Y. Tetrahedron Lett. 2016, 57, 1771.
[45] Singh, M.; Yadav, A. K.; Yadav, L. D. S.; Singh, R. K. P. Synlett 2018, 29, 176.
[46] Li, W.; Yang, C.; Gao, G.-L.; Xia, W.-J. Chin. J. Org. Chem. 2017, 37, 480(in Chinese). (李伟, 杨超, 高国林, 夏吾炯, 有机化学, 2017, 37, 480.)
[47] Castanheiro, T.; Gulea, M.; Donnard, M.; Suffert, J. Eur. J. Org. Chem. 2014, 7814.
[48] Guo, W.; Tan, W.; Zhao, M.; Zheng, L.; Tao, K.; Chen, D.; Fan, X. J. Org. Chem. 2018, 83, 6580.
[49] Frei, R.; Courant, T.; Wodrich, M. D.; Waser, J. Chem.-Eur. J. 2014, 20, 1.
[50] Zhu, D.; Chang, D.-H.; Shi, L. Chem. Commun. 2015, 51, 7180.
[51] Teng, F.; Yu, J.-T.; Yang, H.-T.; Jiang, Y.; Cheng, J. Chem. Commun. 2014, 50, 12139.
[52] Wang, Z.-H.; Ji, X.-M.; Hu, M.-L.; Tang, R.-Y. Tetrahedron Lett. 2015, 56, 5067.
[53] Linderoth, L.; Fristrup, P.; Hansen, M.; Melander, F.; Madsen, R.; Andresen, T. L.; Peters, G. H. J. Am. Chem. Soc. 2009, 131, 12193.
[54] Brown, S. P.; Smith, A. B. Ⅲ J. Am. Chem. Soc. 2015, 137, 4034.
[55] Ke, F.; Qu, Y.-Y.; Jiang, Z.-Q.; Li, Z.-K.; Wu, D.; Zhou, X.-G. Org. Lett. 2011, 13, 454.
[56] Hajipour, A. R.; Pourkaveh, R.; Karimi, H. Appl. Organomet. Chem. 2014, 28, 879.
[57] Pawliczek, M.; Garve, L. K. B.; Werz, D. B. Org. Lett. 2015, 17, 1716.
[58] Lu, X.-G.; Wang, H.-M.; Gao, R.-L.; Sun, D.-M.; Bi, X.-J. RSC Adv. 2014, 4, 28794.
[59] Bisogno, F. R.; Cuetos, A.; Lavandera, I.; Gotor, V. Green Chem. 2009, 11, 452.
[60] Sano, T.; Takagi, T.; Gama, Y.; Shibuya, I.; Shimizu, M. Syn-thesis 2004, 1585.
[61] Wang, F.; Chen, C.; Deng, G.; Xi, C.-J. J. Org. Chem. 2012, 77, 4148.
[62] Finnegan, W. G.; Henry, R. A.; Lofquist, R. J. Am. Chem. Soc. 1958, 80, 3908.
[63] Roh, J.; Artamonova, T. V.; Vavrova, K.; Koldobskii, G. I.; Hrabalek, A. Synthesis 2009, 2175.
[64] Roh, J.; Vavrova, K.; Hrabalek, A. Eur. J. Org. Chem. 2012, 31, 6101.
[65] Yoneyama, H.; Usami, Y.; Komeda, S.; Harusawa, S. Synthesis 2013, 45, 1051.
[66] Vorona, S.; Artamonova, T.; Zevatskii, Y.; Myznikov, L. Syn-thesis 2014, 46, 781.
[67] Marshall, W. S.; Caruthers, M. H. Science 1993, 259, 1564.
[68] Cieslak, J.; Jankowska, J.; Stawinski, J.; Kraszewski, A. J. Org. Chem. 2000, 65, 7049.
[69] Renard, P.-Y.; Schwebel, H.; Vayron, P.; Josien, L.; Valleix, A.; Mioskowski, C. Chem.-Eur. J. 2002, 8, 2910.
[70] Jansa, P.; Cechova, L.; Dracínsky, M.; Janeba, Z. RSC Adv. 2013, 3, 2650.
[71] Gonda, J.; Martinková, M.; Raschmanová, J.; Balentová, E. Tetrahedron:Asymmetry 2006, 17, 1875.
[72] Sundermeier, M.; Zapf, A.; Beller, M.; Sans, S. Tetrahedron Lett. 2001, 42, 6707.
[73] Zhang, Z.-H.; Liebeskind, L. S. Org. Lett. 2006, 8, 4331.
[74] Lee, Y. T.; Choi, S. Y.; Chung, Y. K. Tetrahedron Lett. 2007, 48, 5673.
[75] Potash, S.; Rozen, S. J. Fluorine Chem. 2014, 168, 173.
[76] Jouvin, K.; Matheis, C.; Goossen, L. J. Chem.-Eur. J. 2015, 21, 14324.

硫氰酸酯类化合物的合成及其应用研究进展

Progress on the Synthesis and Applications of Thiocyanates

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