Visible-Light Photocatalytic Remote Thiolation of Aldehydes Triggered by Sulfonylation of Alkenes With Thiosulfonates
- Corresponding author: Zhu Gangguo, gangguo@zjnu.cn
Citation: Yang Junhang, Fu Xiaobo, Lu Zenghui, Zhu Gangguo. Visible-Light Photocatalytic Remote Thiolation of Aldehydes Triggered by Sulfonylation of Alkenes With Thiosulfonates[J]. Acta Chimica Sinica, ;2019, 77(9): 901-905. doi: 10.6023/A19050161
Madasu, S. B.; Vekariya, N. A.; Kiran, M. N. V. D. H.; Gupta, B.; Islam, A.; Douglas, P. S.; Babu, K. R. Beilstein J. Org. Chem. 2012, 8, 1400.
doi: 10.3762/bjoc.8.162
Fromtling, R. A. Drugs Future 1989, 14, 1165.
doi: 10.1358/dof.1989.014.12.109647
Calverley, P. M. A.; Anderson, J. A.; Celli, B.; Ferguson, G. T.; Jenkins, C.; Jones, P. W.; Yates, J. C.; Vestbo, J. N. Engl. J. Med. 2007, 356, 775.
doi: 10.1056/NEJMoa063070
Julia, M.; Paris, J. M. Tetrahedron Lett. 1973, 14, 4833.
doi: 10.1016/S0040-4039(01)87348-2
Olah, G. A.; Mathew, T.; Prakash, G. K. S. Chem. Commun. 2001, 1696.
(a) Deeming, A. S.; Russell, C. J.; Hennessy, A. J.; Willis, M. C. Org. Lett. 2014, 16, 150. (b) Wan, Y.; Zhang, J.; Chen, Y.; Kong, L.; Luo, F.; Zhu, G. Org. Biomol. Chem. 2017, 15, 7204.
(a) Zhou, Q.; Gui, J.; Pan, C.-M.; Albone, E.; Cheng, X.; Suh, E. M.; Grasso, L.; Ishihara, Y.; Baran, P. S. J. Am. Chem. Soc. 2013, 135, 12994. (b) Miao, W.; Zhao, Y.; Ni, C.; Gao, B.; Zhang, W.; Hu, J. J. Am. Chem. Soc. 2018, 140, 880. (c) Griffiths, R. J.; Kong, W. C.; Richards, S. A.; Burley, G. A.; Willis, M. C.; Talbot, E. P. A. Chem. Sci. 2018, 9, 2295.
(a) Liu, T.; Li, Y.; Lai, L.; Cheng, J.; Sun, J.; Wu, J. Org. Lett. 2018, 20, 3605. (b) Ye, S.; Zheng, D.; Wu, J.; Qiu, G. Chem. Commun. 2019, 55, 2214.
(a) Meyer, A. U.; J ger, S.; Hari, D. P.; K nig, B. Adv. Synth. Catal. 2015, 357, 2050. (b) Zhang, G.; Zhang, L.; Yi, H. Luo, Y.; Qi, X.; Tung, C.-H.; Wu, L.-Z.; Lei, A. Chem. Commun. 2016, 52, 10407. (c) Ratushnyy, M.; Kamenova, M.; Gevorgyan, V. Chem. Sci. 2018, 9, 7193. (d) Sun, D.; Zhang, R. Org. Chem. Front. 2018, 5, 92. (e) Cai, S.; Xu, Y.; Chen, D.; Li, L.; Chen, Q.; Huang, M.; Weng, W. Org. Lett. 2016, 18, 2990.
(a) Quebatte, L.; Thommes, K.; Severin, K. J. Am. Chem. Soc. 2006, 128, 7440. (b) Hossain, A.; Engl, S.; Lutsker, E.; Reiser, O. ACS Catal. 2019, 9, 1103. (c) Taniguchi, T.; Idota, A.; Ishibashi, H. Org. Biomol. Chem. 2011, 9, 3151. (d) Pagire, S. K.; Paria, S.; Reiser, O. Org. Lett. 2016, 18, 2106. (e) Xiong, Y.; Sun, Y.; Zhang, G. Org. Lett. 2018, 20, 6250. (f) Rao, W.-H.; Jiang, L.-L.; Liu, X.-M.; Chen, M.-J.; Chen, F.-Y.; Jiang, X.; Zhao, J.-X.; Zou, G.-D.; Zhou, Y.-Q.; Tang, L. Org. Lett. 2019, 21, 2890. (g) Wang, H.; Wang, G.; Lu, Q.; Chiang, C.-W.; Peng, P.; Zhou, J.; Lei, A. Chem. Eur. J. 2016, 22, 14489. (h) Yuan, Y.; Cao, Y.; Lin, Y.; Li, Y.; Huang, Z.; Lei, A. ACS Catal. 2018, 8, 10871.
(a) Gao, Y.; Mei, H.; Han, J.; Pan, Y. Chem. Eur. J. 2018, 24, 17205. (b) Sun, J.; Li, P.; Guo, L.; Yu, F.; He, Y.-P.; Chu, L. Chem. Commun. 2018, 54, 3162. (c) Pirenne, V.; Kurtay, G.; Voci, S.; Bouffier, L.; Sojic, N.; Robert, F.; Bassani, D. M.; Landais, Y. Org. Lett. 2018, 20, 4521.
(a) Chen, Z.-Z.; Liu, S.; Hao, W.-J.; Xu, G.; Wu, S.; Miao, J.-N.; Jiang, B.; Wang, S.-L.; Tu, S.-J.; Li, G. Chem. Sci. 2015, 6, 6654. (b) Huang, M.-H.; Zhu, C.-F.; He, C.-L.; Zhu, Y.-L.; Hao, W.-J.; Wang, D.-C.; Tu, S.-J.; Jiang, B. Org. Chem. Front. 2018, 5, 1643. (c) Wu, W.; Yi, S.; Yu, Y.; Huang, W.; Jiang, H. J. Org. Chem. 2017, 82, 1224. (d) Cao, X.; Cheng, X.; Xuan, J. Org. Lett. 2018, 20, 449.
(a) Zhu, D.; Shao, X.; Hong, X.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2016, 55, 15807. (b) Zhao, Q.; Lu, L.; Shen, Q. Angew. Chem., Int. Ed. 2017, 56, 11575.
(a) Li, H.; Shan, C.; Tung, C.-H.; Xu, Z. Chem. Sci. 2017, 8, 2610. (b) Huang, S.; Thirupathi, N.; Tung, C.-H.; Xu, Z. J. Org. Chem. 2018, 83, 9449.
He, F.-S.; Wu, Y.; Zhang, J.; Xia, H.; Wu, J. Org. Chem. Front. 2018, 5, 2940.
doi: 10.1039/C8QO00824H
(a) Cheng, C.; Liu, S.; Lu, D.; Zhu, G. Org. Lett. 2016, 18, 2852. (b) Nie, X.; Cheng, C.; Zhu, G. Angew. Chem., Int. Ed. 2017, 56, 1898. (c) Jin, W.; Zhou, Y.; Zhao, Y.; Ma, Q.; Kong, L.; Zhu, G. Org. Lett. 2018, 20, 1435. (d) Wan, Y.; Shang, T.; Lu, Z. Zhu, G. Org. Lett. 2019, 21, 4187.
For selected reviews on photocatalysis, see: (a) Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102. (b) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828. (c) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. (d) Xi, Y.; Yi, H.; Lei, A. Org. Biomol. Chem. 2013, 11, 2387. (e) Yu, S.; Zhang, Y.; Wang, R.; Jiang, H.; Cheng, Y.; Kadi, A.; Fun, H.-K. Synthesis 2014, 2711. (f) Xie, J.; Jin, H.; Xu, P.; Zhu, C. Tetrahedron Lett. 2014, 55, 36. (g) Wang, C.; Lu, Z. Org. Chem. Front. 2015, 2, 179. (h) Matsui, J. K.; Lang, S. B.; Heitz, D. R.; Molander, G. A. ACS Catal. 2017, 7, 2563.
For selected reviews, see: (a) Hu, X.-Q.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2017, 56, 1960. (b) Li, W.; Xu, W.; Xie, J.; Yu, S.; Zhu, C. Chem. Soc. Rev. 2018, 47, 654. (c) Stateman, L. M.; Nakafuku, K. M.; Nagib, D. A. Synthesis 2018, 50, 1569. (d) Nechab, M.; Mondal, S.; Bertrand, M. P. Chem. Eur. J. 2014, 20, 16034. For selected reports involving 1, n-HAT since 2018, see: (e) Short, M. A.; Blackburn, J. M.; Roizen, J. L. Angew. Chem., Int. Ed. 2018, 57, 296. (f) Dauncey, E. M.; Morcillo, S. P.; Douglas, J. J.; Sheikh, N. S.; Leonori, D. Angew. Chem., Int. Ed. 2018, 57, 744. (g) Wu, X.; Wang, M.; Huan, L.; Wang, D.; Wang, J.; Zhu, C. Angew. Chem., Int. Ed. 2018, 57, 1640. (h) Wu, S.; Wu, X.; Wang, D.; Zhu, C. Angew. Chem., Int. Ed. 2019, 58, 1499. (i) Jiang, H.; Studer, A. Angew. Chem., Int. Ed. 2018, 57, 1692. (j) Xia, Y.; Wang, L.; Studer, A. Angew. Chem., Int. Ed. 2018, 57, 12940. (k) Ratushnyy, M.; Parasram, M.; Wang, Y.; Gevorgyan, V. Angew. Chem., Int. Ed. 2018, 57, 2712. (l) Chuentragool, P.; Yadagiri, D.; Morita, T.; Sarkar, S.; Parasram, M.; Wang, Y.; Gevorgyan, V. Angew. Chem., Int. Ed. 2019, 58, 1794. (m) Na, C. G.; Alexanian, E. J. Angew. Chem., Int. Ed. 2018, 57, 13106. (n) Li, Z.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2018, 57, 13288. (o) Bao, X.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2019, 58, 2139. (p) Kim, I.; Park, B.; Kang, G.; Kim, J.; Jung, H.; Lee, H.; Baik, M.-H.; Hong, S. Angew. Chem., Int. Ed. 2018, 57, 15517. (q) Guan, H.; Sun, S.; Mao, Y.; Chen, L.; Lu, R.; Huang, J.; Liu, L. Angew. Chem., Int. Ed. 2018, 57, 11413. (r) Hu, A.; Guo, J.-J.; Pan, H.; Tang, H.; Gao, Z.; Zuo, Z. J. Am. Chem. Soc. 2018, 140, 1612. (s) An, X.-D.; Jiao, Y.-Y.; Zhang, H.; Gao, Y.; Yu, S. Org. Lett. 2018, 20, 401. (t) Zhu, Y.; Huang, K.; Pan, J.; Qiu, X.; Luo, X.; Qin, Q.; Wei, J.; Wen, X.; Zhang, L.; Jiao, N. Nat. Commun. 2018, 9, 2625. (u) Li, G.-X.; Hu, X.; He, G.; Chen, G. Chem. Sci. 2019, 10, 688. (v) Zhang, Z.; Stateman, L. M.; Nagib, D. A. Chem. Sci. 2019, 10, 1207. (w) Wu, K.; Wang, L.; Colón-Rodríguez, S.; Flechsig, G.-U.; Wang, T. Angew. Chem., Int. Ed. 2019, 58, 1774. (x) Liu, Z.; Xiao, H.; Zhang, B.; Shen, H.; Zhu, L.; Li, C. Angew. Chem., Int. Ed. 2019, 58, 2510.
Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
Bo YANG , Gongxuan LÜ , Jiantai MA . Nickel phosphide modified phosphorus doped gallium oxide for visible light photocatalytic water splitting to hydrogen. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 736-750. doi: 10.11862/CJIC.20230346
Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
Jinyao Du , Xingchao Zang , Ningning Xu , Yongjun Liu , Weisi Guo . Electrochemical Thiocyanation of 4-Bromoethylbenzene. University Chemistry, 2024, 39(6): 312-317. doi: 10.3866/PKU.DXHX202310039
Bing LIU , Huang ZHANG , Hongliang HAN , Changwen HU , Yinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO2 mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398
Jie Li , Huida Qian , Deyang Pan , Wenjing Wang , Daliang Zhu , Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076
Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
Guangming YIN , Huaiyao WANG , Jianhua ZHENG , Xinyue DONG , Jian LI , Yi'nan SUN , Yiming GAO , Bingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C3N4 nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086
Peng GENG , Guangcan XIANG , Wen ZHANG , Haichuang LAN , Shuzhang XIAO . Hollow copper sulfide loaded protoporphyrin for photothermal-sonodynamic therapy of cancer cells. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1903-1910. doi: 10.11862/CJIC.20240155
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
Fengqiao Bi , Jun Wang , Dongmei Yang . Specialized Experimental Design for Chemistry Majors in the Context of “Dual Carbon”: Taking the Assembly and Performance Evaluation of Zinc-Air Fuel Batteries as an Example. University Chemistry, 2024, 39(4): 198-205. doi: 10.3866/PKU.DXHX202311069
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
Hongsheng Tang , Yonghe Zhang , Dexiang Wang , Xiaohui Ning , Tianlong Zhang , Yan Li , Hua Li . A Wonderful Journey through the Kingdom of Hazardous Chemicals. University Chemistry, 2024, 39(9): 196-202. doi: 10.12461/PKU.DXHX202403098
Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
Qin Hu , Liuyun Chen , Xinling Xie , Zuzeng Qin , Hongbing Ji , Tongming Su . Ni掺杂构建电子桥及激活MoS2惰性基面增强光催化分解水产氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2406024-. doi: 10.3866/PKU.WHXB202406024
Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024
Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002