Recent Advances on the Photocatalytic and Electrocatalytic Thiocyanation Reactions
- Corresponding author: Wen Jiangwei, wenjy@qfnu.edu.cn Wang Hua, huawang@qfnu.edu.cn
Citation:
Zhang Longfei, Niu Cong, Yang Xiaoting, Qin Hongyun, Yang Jianjing, Wen Jiangwei, Wang Hua. Recent Advances on the Photocatalytic and Electrocatalytic Thiocyanation Reactions[J]. Chinese Journal of Organic Chemistry,
;2020, 40(5): 1117-1128.
doi:
10.6023/cjoc201912011
(a) Capon, R. J.; Skene, C.; Liu, E. H.-T.; Lacey, E.; Gill, J. H.; Heiland, K.; Friedel, T. J. Org. Chem. 2001, 66, 7765.
(b) Dutta, S.; Abe, H.; Aoyagi, S.; Kibayashi, C.; Gates, K. S. J. Am. Chem. Soc. 2005, 127, 15004.
(c) Elhalem, E.; Bailey, B. N.; Docampo, R.; Ujváry, I.; Szajnman, S. H.; Rodriguez, J. B. J. Med. Chem. 2002, 45, 3984.
(d) Kokorekin, V.; Terent'ev, A.; Ramenskaya, G.; Grammatikova, N.; Rodionova, G.; Ilovaiskii, A. Pharm. Chem. J. 2013, 47, 422.
(e) Yasman, Y.; Edrada, R. A.; Wray, V.; Proksch, P. J. Nat. Prod. 2003, 66, 1512.
(a) Khalili, D. Chin. Chem. Lett. 2015, 26, 547.
(b) Zeng, Y.-F.; Tan, D.-H.; Chen, Y.; Lv, W.-X.; Liu, X.-G.; Li, Q.; Wang, H. Org. Chem. Front. 2015, 2, 1511.
(c) Guo, L.-N.; Gu, Y.-R.; Yang, H.; Hu, J. Org. Biomol. Chem. 2016, 14, 3098.
(d) Khalili, D. New J. Chem. 2016, 40, 2547.
(e) Chen, Q.; Lei, Y.; Wang, Y.; Wang, C.; Wang, Y.; Xu, Z.; Wang, H.; Wang, R. Org. Chem. Front. 2017, 4, 369.
(f) Ji, F.; Fan, Y.; Yang, R.; Yang, Y.; Yu, D.; Wang, M.; Li, Z. Asian J. Org. Chem. 2017, 6, 682.
(g) Jiang, G.; Zhu, C.; Li, J.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2017, 359, 1208.
(h) Prieto, A.; Uzel, A.; Bouyssi, D.; Monteiro, N. Eur. J. Org. Chem. 2017, 2017, 4201.
(i) Chen, Y.; Wang, S.; Jiang, Q.; Cheng, C.; Xiao, X.; Zhu, G. J. Org. Chem. 2018, 83, 716.
(j) Khaikate, O.; Meesin, J.; Pohmakotr, M.; Reutrakul, V.; Leowanawat, P.; Soorukram, D.; Kuhakarn, C. Org. Biomol. Chem. 2018, 16, 8553.
(k) Qiu, J.; Wu, D.; Karmaker, P. G.; Yin, H.; Chen, F.-X. Org. Lett. 2018, 20, 1600.
(l) Wu, C.; Lu, L.-H.; Peng, A.-Z.; Jia, G.-K.; Peng, C.; Cao, Z.; Tang, Z.; He, W.-M.; Xu, X. Green Chem. 2018, 20, 3683.
(m) Dey, A.; Hajra, A. Adv. Synth. Catal. 2019, 361, 842.
(n) Noikham, M.; Yotphan, S. Eur. J. Org. Chem. 2019, 2019, 2759.
Castanheiro, T.; Suffert, J.; Donnard, M.; Gulea, M. Chem. Soc. Rev. 2016, 45, 494.
doi: 10.1039/C5CS00532A
Vekariya, R. H.; Patel, H. D. Synth. Commun. 2017, 47, 87.
doi: 10.1080/00397911.2016.1255973
Yadav, A. K.; Yadav, L. D. S. Tetrahedron Lett. 2015, 56, 6696.
doi: 10.1016/j.tetlet.2015.10.048
Yuan, P.-F.; Zhang, Q.-B.; Jin, X.-L.; Lei, W.-L.; Wu, L.-Z.; Liu, Q. Green Chem. 2018, 20, 5464.
doi: 10.1039/C8GC02720J
Guy, R. G.; Thompson, J. J. Tetrahedron 1978, 34, 541.
doi: 10.1016/0040-4020(78)80049-0
Chen, Y.-J.; He, Y.-H.; Guan, Z. Tetrahedron 2019, 75, 3053.
doi: 10.1016/j.tet.2019.04.053
Zhang, D.; Wang, H.; Bolm, C. Chem. Commun. 2018, 54, 5772.
doi: 10.1039/C8CC03178A
Gao, Y.; Liu, Y.; Wan, J.-P. J. Org. Chem. 2019, 84, 2243.
doi: 10.1021/acs.joc.8b02981
Fan, W.; Yang, Q.; Xu, F.; Li, P. J. Org. Chem. 2014, 79, 10588.
doi: 10.1021/jo5015799
Wang, L.; Wang, C.; Liu, W.; Chen, Q.; He, M. Tetrahedron Lett. 2016, 57, 1771.
doi: 10.1016/j.tetlet.2016.03.028
Hosseini-Sarvari, M.; Hosseinpour, Z.; Koohgard, M. New J. Chem. 2018, 42, 19237.
doi: 10.1039/C8NJ03128B
Yang, D.; Yan, K.; Wei, W.; Li, G.; Lu, S.; Zhao, C.; Tian, L.; Wang, H. J. Org. Chem. 2015, 80, 11073.
doi: 10.1021/acs.joc.5b01637
Mitra, S.; Ghosh, M.; Mishra, S.; Hajra, A. J. Org. Chem. 2016, 47, 8275.
Singh, M.; Yadav, A. K.; Yadav, L. D. S.; Singh, R. Synlett 2018, 29, 176.
doi: 10.1055/s-0036-1590921
Chauhan, P.; Ritu, R.; Preeti, P.; Kumar, S.; Jain, N. Eur. J. Org. Chem. 2019, 2019, 4334.
Tambe, S. D.; Jadhav, M. S.; Rohokale, R. S.; Kshirsagar, U. A. Eur. J. Org. Chem. 2018, 2018, 4867.
Gullapalli, K.; Vijaykumar, S. Org. Biomol. Chem. 2019, 17, 2232.
doi: 10.1039/C9OB00054B
(a) Zhao, Y.; Wang, H.; Hou, X.; Hu, Y.; Lei, A.; Zhang, H.; Zhu, L. J. Am. Chem. Soc. 2006, 128, 15048.
(b) Li, C.-J. Acc. Chem. Res. 2009, 42, 335.
(c) Chen, M.; Zheng, X.; Li, W.; He, J.; Lei, A. J. Am. Chem. Soc. 2010, 132, 4101.
(d) Le Bras, J.; Muzart, J. Chem. Rev. 2011, 111, 1170.
(e) Liu, C.; Zhang, H.; Shi, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
(f) Shi, W.; Liu, C.; Lei, A. Chem. Soc. Rev. 2011, 40, 2761.
(g) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
(h) He, C.; Guo, S.; Ke, J.; Hao, J.; Xu, H.; Chen, H.; Lei, A. J. Am. Chem. Soc. 2012, 134, 5766.
(i) Girard, S. A.; Knauber, T.; Li, C. J. Angew. Chem., Int. Ed. 2014, 53, 74.
(j) Liu, C.; Liu, D.; Lei, A. Acc. Chem. Res. 2014, 47, 3459.
(k) Liu, C.; Yuan, J.; Gao, M.; Tang, S.; Li, W.; Shi, R.; Lei, A. Chem. Rev. 2015, 115, 12138.
(l) Zhang, G.; Liu, C.; Yi, H.; Meng, Q.; Bian, C.; Chen, H.; Jian, J.-X.; Wu, L.-Z.; Lei, A. J. Am. Chem. Soc. 2015, 137, 9273.
(m) Song, C.; Yi, H.; Dou, B.; Li, Y.; Singh, A. K.; Lei, A. Chem. Commun. 2017, 53, 3689.
(n) Song, C.; Dong, X.; Yi, H.; Chiang, C.-W.; Lei, A. ACS Catal. 2018, 8, 2195.
(o) Song, C.; Liu, K.; Dong, X.; Chiang, C.-W.; Lei, A. Synlett 2019, 30, 1149.
Kang, L.-S.; Luo, M.-H.; Lam, C. M.; Hu, L.-M.; Little, R. D.; Zeng, C.-C. Green Chem. 2016, 18, 3767.
doi: 10.1039/C6GC00666C
Liang, S.; Zeng, C. C.; Tian, H.; Sun, B.; Ren, F. Adv. Synth. Catal. 2018, 360, 1444.
doi: 10.1002/adsc.201701401
De Klein, W. J. Electrochim. Acta 1973, 18, 413.
doi: 10.1016/0013-4686(73)80044-1
Levy, A.; Becker, J. Y. Electrochim. Acta 2015, 178, 294.
doi: 10.1016/j.electacta.2015.07.127
Gitkis, A.; Becker, J. Y. Electroanalysis 2016, 28, 2802.
doi: 10.1002/elan.201600197
Wen, J.; Zhang, L.; Yang, X.; Niu, C.; Wang, S.; Wei, W.; Sun, X.; Yang, J.; Wang, H. Green Chem. 2019, 21, 3597.
doi: 10.1039/C9GC01351B
Krishnan, P.; Gurjar, V. G. Synth. Commun. 1992, 22, 2741.
doi: 10.1080/00397919208021538
Krishnan P., Gurjar V. G.. J.[J]. Appl. Electrochem., 1995,25(792).
Gitkis, A.; Becker, J. Y. J. Electroanal. Chem. 2006, 593, 29.
Gitkis, A.; Becker, J. Y. Electrochim. Acta 2010, 55, 5854.
doi: 10.1016/j.electacta.2010.05.035
(a) Nair, V.; George, T. G.; Nair, L. G.; Panicker, S. B. Tetrahedron Lett. 1999, 40, 1195.
(b) Chakrabarty, M.; Sarkar, S. Tetrahedron Lett. 2003, 44, 8131.
(c) Yadav, J.; Reddy, B.; Shubashree, S.; Sadashiv, K. Tetrahedron Lett. 2004, 45, 2951.
(d) Yadav, J.; Reddy, B.; Krishna, A.; Reddy, C. S.; Narsaiah, A. Synthesis 2005, 2005, 961.
(e) Pan, X.-Q.; Lei, M.-Y.; Zou, J.-P.; Zhang, W. Tetrahedron Lett. 2009, 50, 347.
(f) Akhlaghinia, B.; Pourali, A.-R.; Rahmani, M. Synth. Commun. 2012, 42, 1184.
(g) Khazaei, A.; Zolfigol, M. A.; Mokhlesi, M.; Panah, F. D.; Sajjadifar, S. Helv. Chim. Acta 2012, 95, 106.
Fotouhi, L.; Nikoofar, K. Tetrahedron Lett. 2013, 54, 2903.
doi: 10.1016/j.tetlet.2013.02.106
Kokorekin, V. A.; Sigacheva, V. L.; Petrosyan, V. A. Tetrahedron Lett. 2014, 55, 4306.
doi: 10.1016/j.tetlet.2014.06.028
Zhang, X.; Wang, C.; Jiang, H.; Sun, L. RSC Adv. 2018, 8, 22042.
doi: 10.1039/C8RA04407D
Yaubasarova, R. R.; Kokorekin, V. A.; Ramenskaya, G. V.; Petrosyan, V. A. Mendeleev Commun. 2019, 29, 334.
doi: 10.1016/j.mencom.2019.05.032
Sun, L.; Zhang, X.; Li, Z.; Ma, J.; Zeng, Z.; Jiang, H. Eur. J. Org. Chem. 2018, 2018, 4949.
doi: 10.1002/ejoc.201800267
Kokorekin, V. A.; Yaubasarova, R. R.; Neverov, S. V.; Petrosyan, V. A. Mendeleev Commun. 2016, 5, 413.
Kokorekin, V. A.; Yaubasarova, R. R.; Neverov, S. V.; Petrosyan, V. A. Eur. J. Org. Chem. 2019, 2019, 4233.
doi: 10.1002/ejoc.201900390
Dyga, M.; Hayrapetyan, D.; Rit, R. K.; Gooßen, L. J. Adv. Synth. Catal. 2019, 361, 3548.
doi: 10.1002/adsc.201900156
Yang, S.-M.; He, T.-J.; Lin, D.-Z.; Huang, J.-M. Org. Lett. 2019, 21, 1958.
doi: 10.1021/acs.orglett.8b04136
Tongtong Zhao , Yan Wang , Shiyue Qin , Liang Xu , Zhenhua Li . New Experiment Development: Upgrading and Regeneration of Discarded PET Plastic through Electrocatalysis. University Chemistry, 2024, 39(3): 308-315. doi: 10.3866/PKU.DXHX202309003
Xueting Cao , Shuangshuang Cha , Ming Gong . 电催化反应中的界面双电层:理论、表征与应用. Acta Physico-Chimica Sinica, 2025, 41(5): 100041-. doi: 10.1016/j.actphy.2024.100041
Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
Jianchun Wang , Ruyu Xie . The Fantastical Dance of Miss Electron: Contra-Thermodynamic Electrocatalytic Reactions. University Chemistry, 2025, 40(4): 331-339. doi: 10.12461/PKU.DXHX202406082
Fangfang WANG , Jiaqi CHEN , Weiyin SUN . CuBi@Cu-MOF composite catalysts for electrocatalytic CO2 reduction to HCOOH. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 97-104. doi: 10.11862/CJIC.20240350
Jinyi Sun , Lin Ma , Yanjie Xi , Jing Wang . Preparation and Electrocatalytic Nitrogen Reduction Performance Study of Vanadium Nitride@Nitrogen-Doped Carbon Composite Nanomaterials: A Recommended Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(4): 184-191. doi: 10.3866/PKU.DXHX202310094
Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . 碳修饰的铜催化剂实现安培级电流电化学还原CO2制C2+产物. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-. doi: 10.3866/PKU.WHXB202404012
Kun WANG , Wenrui LIU , Peng JIANG , Yuhang SONG , Lihua CHEN , Zhao DENG . Hierarchical hollow structured BiOBr-Pt catalysts for photocatalytic CO2 reduction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1270-1278. doi: 10.11862/CJIC.20240037
Zhuo WANG , Junshan ZHANG , Shaoyan YANG , Lingyan ZHOU , Yedi LI , Yuanpei LAN . Preparation and photocatalytic performance of CeO2-reduced graphene oxide by thermal decomposition. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1708-1718. doi: 10.11862/CJIC.20240067
Jianyin He , Liuyun Chen , Xinling Xie , Zuzeng Qin , Hongbing Ji , Tongming Su . ZnCoP/CdLa2S4肖特基异质结的构建促进光催化产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2404030-. doi: 10.3866/PKU.WHXB202404030
Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
Yuanyin Cui , Jinfeng Zhang , Hailiang Chu , Lixian Sun , Kai Dai . Rational Design of Bismuth Based Photocatalysts for Solar Energy Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2405016-. doi: 10.3866/PKU.WHXB202405016
Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO2 Reduction by Modified g-C3N4. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
Zijian Jiang , Yuang Liu , Yijian Zong , Yong Fan , Wanchun Zhu , Yupeng Guo . Preparation of Nano Zinc Oxide by Microemulsion Method and Study on Its Photocatalytic Activity. University Chemistry, 2024, 39(5): 266-273. doi: 10.3866/PKU.DXHX202311101
Xia ZHANG , Yushi BAI , Xi CHANG , Han ZHANG , Haoyu ZHANG , Liman PENG , Shushu HUANG . Preparation and photocatalytic degradation performance of rhodamine B of BiOCl/polyaniline. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 913-922. doi: 10.11862/CJIC.20240255
Ruolin CHENG , Haoran WANG , Jing REN , Yingying MA , Huagen LIANG . Efficient photocatalytic CO2 cycloaddition over W18O49/NH2-UiO-66 composite catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 523-532. doi: 10.11862/CJIC.20230349
Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO2 Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
Jingyu Cai , Xiaoyu Miao , Yulai Zhao , Longqiang Xiao . Exploratory Teaching Experiment Design of FeOOH-RGO Aerogel for Photocatalytic Benzene to Phenol. University Chemistry, 2024, 39(4): 169-177. doi: 10.3866/PKU.DXHX202311028
Yulian Hu , Xin Zhou , Xiaojun Han . A Virtual Simulation Experiment on the Design and Property Analysis of CO2 Reduction Photocatalyst. University Chemistry, 2025, 40(3): 30-35. doi: 10.12461/PKU.DXHX202403088
Ronghui LI . Photocatalysis performance of nitrogen-doped CeO2 thin films via ion beam-assisted deposition. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1123-1130. doi: 10.11862/CJIC.20240440