Cu-Catalyzed Direct Arylation of Benzothiazoles with Diaryliodonium Salts
- Corresponding author: Du Zhengyin, clinton_du@126.com Fu Ying, fu_yingmail@126.com
Citation:
Li Huaigui, Yang Peng, Xu Zheng, Du Zhengyin, Fu Ying. Cu-Catalyzed Direct Arylation of Benzothiazoles with Diaryliodonium Salts[J]. Chinese Journal of Organic Chemistry,
;2020, 40(8): 2476-2482.
doi:
10.6023/cjoc202002042
Matysiak, J.; Skrzypek, A.; Głaszcz, U.; Matwijczuk, A.; Senczyna, B.; Wietrzyk, J.; Krajewska-Kułak, E.; Niewiadomy, A. Res. Chem. Intermed. 2018, 44, 6169.
doi: 10.1007/s11164-018-3483-0
Choi, S.; Park, H.; Lee, S.; Kim, S.; Hanc G.; Choo, H. Bioorg. Med. Chem. 2006, 14, 1229.
doi: 10.1016/j.bmc.2005.09.051
Guo, H.; Li, J.; Shang, Y. Chin. Chem. Lett. 2009, 20, 1408.
doi: 10.1016/j.cclet.2009.06.037
Benazzouz, A.; Boraud, T.; Dubédat, P.; Boireau, A.; Stutzmann, J.; Gross, C. Eur. J. Pharmacol. 1995, 284, 299.
doi: 10.1016/0014-2999(95)00362-O
Bheeter, C. B.; Chen, L.; Soulé, J.-F.; Doucet, H. Catal. Sci. Technol. 2016, 6, 2005.
doi: 10.1039/C5CY02095F
(a) Hu, R.; Li, X.; Tong, Y.; Miao, D.; Pan, Q.; Jiang, Z.; Gan, H.; Han, S. Synlett 2016, 27, 1387.
(b) Yuen, O. Y.; So, C. M.; Wong, W. T.; Kwong, F. Y. Synlett 2013, 1549.
(c) Nagao, I.; Ishizaka T.; Kawanami, H. Green Chem. 2016, 18, 3494.
(a) Zhang, G.; Liu, C.; Yi, H.; Meng, Q.; Bian, C.; Chen, H.; Jian, J.; Wu, L.; Lei, A. J. Am. Chem. Soc. 2015, 137, 9273.
(b) Inamoto, K.; Nozawa, K.; Kondo, Y. Synlett 2012, 1678.
(c) Inamoto, K.; Hasegawa, C.; Kawasaki, J.; Hiroya, K.; Dohi, T. Adv. Synth. Catal. 2010, 352, 2643.
(d) Urzua, J. I.; Contreras, R.; Salas, C. O.; Tapia, R. A. RSC Adv. 2016, 6, 82401.
(e) Wang, P.; Tang, S. Green Chem. 2017, 19, 2092.
(f) Xu, Z.; Li, H.; Li, D. H.; Lang. J. Org. Lett. 2019, 21, 237.
(a) Huang, C.; Wu, J.; Song, C.; Ding, R.; Qiao, Y.; Hou, H.; Chang, J.; Fan, Y. Chem. Commun. 2015, 51, 10353.
(b) Kirchberg, S.; Tani, S.; Ueda, K.; Yamaguchi, J.; Studer, A.; Itami, K. Angew. Chem., Int. Ed. 2011, 50, 2387.
(c) Zhang, F.; Greaney. M. Angew. Chem., Int. Ed. 2010, 49, 2768.
(d) Khake, S. M.; Soni, V.; Gonnade, B. R.; Punji, B. Dalton Trans. 2014, 43, 16084.
(e) Yang, J. Tetrahedron 2019, 75, 2182.
(f) Liu, C.; Yang, F. Chin. J. Chem. 2016, 34, 1213.
(g) Feng, J.; Li, B.; Jiang, J. Chin. J. Chem. 2018, 36, 11.
(a) Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656.
(b) Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052.
(a) Wirth, T. Angew. Chem., Int Ed. 2001, 40, 2812.
(b) Cai, Q.; Ma, H. Acta Chim. Sinica 2019, 77, 213(in Chinese). (蔡倩, 马浩文, 化学学报, 2019, 77, 213.)
(c) Wang, M.; Jiang, X. Acta Chim. Sinica 2018, 76, 377(in Chinese). (王明, 姜雪峰, 化学学报, 2018, 76, 377.)
Kalyani, D.; Deprez, N. R.; Desai, N. R.; Sanford, L. V.; Kalyani, D.; Deprez, N. R.; Desai, L.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
doi: 10.1021/ja051402f
Wu, X.; Yang, Y.; Han, J.; Wang, L. Org. Lett. 2015, 17, 5654.
doi: 10.1021/acs.orglett.5b02938
Suero, M. G.; Bayle, E. D.; Collins, B. L.; Gaunt, M. J. Am. Chem. Soc. 2013, 135, 5332.
doi: 10.1021/ja401840j
Margraf, N.; Manolikakes, G. J. Org. Chem. 2015, 80, 2582.
doi: 10.1021/jo5027518
Antonchick, A. P.; Samanta, R.; Kulikov, K.; Lategahn, J. Angew. Chem., Int. Ed. 2011, 50, 8605.
doi: 10.1002/anie.201102984
Phipps, R. J.; Grimster, N. P.; Gaunt, M. J. J. Am. Chem. Soc. 2008, 130, 8172.
doi: 10.1021/ja801767s
Qian, X.; Han, J.; Wang, L. Tetrahedron Lett. 2016, 57, 607.
doi: 10.1016/j.tetlet.2015.12.100
Zhu, D.; Liu, P.; Lu, W.; Wang, H.; Luo, B.; Hu, Y.; Huang, P.; Wen, S. Chem.-Eur. J. 2015, 21, 18915.
doi: 10.1002/chem.201503791
Yang, P.; Wang, R.; Wu, H.; Du, Z.; Fu, Y. Asian J. Org. Chem. 2017, 6, 184.
doi: 10.1002/ajoc.201600514
Gang, F.; Che, Y.; Du, Z.; Feng, H.; Fu, Y. Synlett 2017, 28, 1624.
doi: 10.1055/s-0036-1588815
(a) Zhang, W.; Dong, T.; Wang, T.; Du, Z. J. Liaocheng Univ. (Nat. Sci. Ed.) 2019, 32, 35(in Chinese).
(张文莹, 董涛生, 王天昀, 杜正银, 聊城大学学报(自然科学版), 2019, 32, 35.)
(b) Hu, B.; Zhang, Y.; Wang, T.; Du, Z. J. Liaocheng Univ. (Nat. Sci. Ed.) 2020, 33, 67(in Chinese).
(胡贝, 张源民, 王天昀, 杜正银, 聊城大学学报(自然科学版), 2020, 33, 67.)
(c) Gang, F.; Xu, G.; Dong, T.; Yang, L.; Du, Z. Chin. J. Org. Chem. 2015, 35, 1428(in Chinese).
(刚芳莉, 徐光利, 董涛生, 杨丽, 杜正银, 有机化学, 2015, 35, 1428.)
(a) Kumar, D.; Pilania, M.; Arun, V.; Pooniya, S. Org. Biomol. Chem. 2014, 12, 6340.
(b) Zhou, B.; Hou, W.; Yang, Y.; Feng, H.; Li, Y. Org. Lett. 2014, 16, 1322.
Deng, H.; Li, Z.; Ke, F.; Zhou, X. Chem.-Eur. J. 2012, 18, 4840.
doi: 10.1002/chem.201103525
Yang, Z.; Chen, X.; Wang, S.; Liu, J.; Xie, K.; Wang, A.; Tan, Z. J. Org. Chem. 2012, 77, 7086.
doi: 10.1021/jo300740j
Duan, Z.; Ranjit, S.; Liu, X. Org. Lett. 2010, 12, 2430.
doi: 10.1021/ol100816g
Song, Q.; Feng, Q.; Zhou, M. Org. Lett. 2013, 15, 5990.
doi: 10.1021/ol402871f
Pratap, U. R.; Mali, J. R.; Jawale, D. W.; Mane, R. A. Tetrahedron Lett. 2009, 50, 1352.
doi: 10.1016/j.tetlet.2009.01.032
Prasad, D.; Sekar, G. Org. Lett. 2011, 13, 1008.
doi: 10.1021/ol103041s
Inamoto, K.; Hasegawa, C.; Hiroya, K.; Doi, T. Org. Lett. 2008, 10, 5147.
doi: 10.1021/ol802033p
Alla, S. K.; Sadhu, P.; Punniyamurthy, T. J. Org. Chem. 2014, 79, 7502.
doi: 10.1021/jo501216h
Liu, S.; Chen, R.; Guo, X.; Yang, H.; Deng, G.; Li. C. Green Chem. 2012, 14, 1577.
Auld, D. S.; Zhang, Y. Q.; Southal, N. T.; Rai, G.; Landsman, M.; MacLure, D.; Langevin, C. J.; Thomas, C. P.; Inglese, J. J. Med. Chem. 2009, 52, 1450.
doi: 10.1021/jm8014525
Weekes. A. A.; Bagley, M. C.; Westwell, A. D. Tetrahedron 2011, 67, 7743.
doi: 10.1016/j.tet.2011.08.004
Sayama, S. Heterocycles 2011, 83, 1267.
doi: 10.3987/COM-11-12178
Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543
Chao Chen , Wenwen Yu , Guangen Huang , Xuelian Ren , Xiangli Chen , Yixin Li , Shenggui Liang , Mengmeng Xu , Mingyue Zheng , Yaxi Yang , He Huang , Wei Tang , Bing Zhou . Asymmetric macrocyclization enabled by Rh(Ⅲ)-catalyzed CH activation: Enantioenriched macrocyclic inhibitor of Zika virus infection. Chinese Chemical Letters, 2024, 35(11): 109574-. doi: 10.1016/j.cclet.2024.109574
Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp3)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445
Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
Yuhan Liu , Jingyang Zhang , Gongming Yang , Jian Wang . Highly enantioselective carbene-catalyzed δ-lactonization via radical relay cross-coupling. Chinese Chemical Letters, 2025, 36(1): 109790-. doi: 10.1016/j.cclet.2024.109790
Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
Xin Li , Jia-Min Lu , Bo Li , Chen Zhao , Bei-Bei Yang , Li Li . Chiroptical sensing for remote chiral amines via a C–H activation reaction. Chinese Chemical Letters, 2025, 36(5): 110310-. doi: 10.1016/j.cclet.2024.110310
Peng Guo , Shicheng Dong , Xiang-Gui Zhang , Bing-Bin Yang , Jun Zhu , Ke-Yin Ye . Cobalt-catalyzed migratory carbon-carbon cross-coupling of borabicyclo[3.3.1]nonane (9-BBN) borates. Chinese Chemical Letters, 2025, 36(4): 110052-. doi: 10.1016/j.cclet.2024.110052
Yue Sun , Liming Yang , Yaohang Cheng , Guanghui An , Guangming Li . Pd(I)-catalyzed ring-opening arylation of cyclopropyl-α-aminoamides: Access to α-ketoamide peptidomimetics. Chinese Chemical Letters, 2024, 35(6): 109250-. doi: 10.1016/j.cclet.2023.109250
Rong-Nan Yi , Wei-Min He . Electron donor-acceptor complex enabled arylation of dithiocarbamate anions with thianthrenium salts under aqueous micellar conditions. Chinese Chemical Letters, 2024, 35(11): 110194-. doi: 10.1016/j.cclet.2024.110194
Qiao Song , Xue Peng , Zhouyu Wang , Leyong Wang . Iron-catalyzed C–H activation: A sustainable approach to efficient organic synthesis. Chinese Chemical Letters, 2025, 36(5): 110869-. doi: 10.1016/j.cclet.2025.110869
Shengkai Li , Yuqin Zou , Chen Chen , Shuangyin Wang , Zhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147
Xiangyang Ji , Yishuang Chen , Peng Zhang , Shaojia Song , Jian Liu , Weiyu Song . Boosting the first C–H bond activation of propane on rod-like V/CeO2 catalyst by photo-assisted thermal catalysis. Chinese Chemical Letters, 2025, 36(5): 110719-. doi: 10.1016/j.cclet.2024.110719
Yuhao Zhou , Siyuan Wu , Xiaozhe Ren , Hongjin Li , Shu Li , Tianying Yan . Effects of salt fraction on the Na+ transport in salt-in-ionic liquid electrolytes. Chinese Chemical Letters, 2025, 36(6): 110048-. doi: 10.1016/j.cclet.2024.110048
Shuai Tang , Zian Wang , Mengyi Zhu , Xinyun Zhao , Xiaoyun Hu , Hua Zhang . Synthesis of organoboron compounds via heterogeneous C–H and C–X borylation. Chinese Chemical Letters, 2025, 36(5): 110503-. doi: 10.1016/j.cclet.2024.110503
Qiangwei Wang , Huijiao Liu , Mengjie Wang , Haojie Zhang , Jianda Xie , Xuanwei Hu , Shiming Zhou , Weitai Wu . Observation of high ionic conductivity of polyelectrolyte microgels in salt-free solutions. Chinese Chemical Letters, 2024, 35(4): 108743-. doi: 10.1016/j.cclet.2023.108743
Kailong Zhang , Chao Zhang , Luanhui Wu , Qidong Yang , Jiadong Zhang , Guang Hu , Liang Song , Gaoran Li , Wenlong Cai . Chloride molten salt derived attapulgite with ground-breaking electrochemical performance. Chinese Chemical Letters, 2024, 35(10): 109618-. doi: 10.1016/j.cclet.2024.109618