Synthesis of Vinyl-Substituted Dihydroisoquinolone via Ru(Ⅱ)-Catalyzed C—H Functionalization/Annulation of Imidates
- Corresponding author: Lin Cong, conglin0127@jxstnu.com.cn Shen Liang, liangshen@jxstnu.com.cn
Citation:
Lin Cong, Gao Zhenbo, Teng Qiuxun, Xue Bowen, Li Xiaohua, Gao Fei, Shen Liang. Synthesis of Vinyl-Substituted Dihydroisoquinolone via Ru(Ⅱ)-Catalyzed C—H Functionalization/Annulation of Imidates[J]. Chinese Journal of Organic Chemistry,
;2020, 40(9): 2863-2870.
doi:
10.6023/cjoc202004048
(a) Danishefsky, S.; Lee, J. Y. J. Am. Chem. Soc. 1989, 111, 4829.
(b) Baxendale, I. R.; Ley, S. V.; Piutti, C. Angew. Chem., Int. Ed. 2002, 41, 219.
(c) Moser, W. H.; Zhang, J.; Lecher, C. S.; Frazier, T. L.; Pink, M. Org. Lett. 2002, 4, 1981.
(a) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
(b) Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
(c) Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147.
(d) Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215.
(e) Liu, C.; Zhang, H.; Sui, W.; Lei, A. Chem. Rev. 2011, 111, 1780.
(f) Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Commun. 2010, 46, 677.
(g) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726.
(h) Castro, L. C. M.; Chatani, N. Chem. Lett. 2015, 44, 410.
(i) Petrone, D. A.; Ye, J.; Lautens, M. Chem. Rev. 2016, 116, 8003.
(j) Gensch, T.; Hopkinson, M. N.; Glorius, F.; Wencel-Delord, J. Chem. Soc. Rev. 2016, 45, 2900.
(k) Kim, D.-S.; Park, W.-J.; Jun, C.-H. Chem. Rev. 2017, 117, 8977.
(l) Park, Y.; Kim, Y.; Chang, S. Chem. Rev. 2017, 117, 9247.
(m) Santhoshkumar, R.; Cheng, C.-H. Chem.-Eur. J. 2019, 25, 9366.
(n) Rej, S.; Chatani, N. Angew. Chem., Int. Ed. 2019, 58, 8304.
(o) Luo, F. Chin. J. Org. Chem. 2019, 39, 3084(in Chinese). (罗飞华, 有机化学, 2019, 39, 3084).
(p) Wang, S.; Yan, F.; Wang, L.; Zhu, L. Chin. J. Org. Chem. 2018, 38, 291(in Chinese). (汪珊, 严沣, 汪连生, 朱磊, 有机化学, 2018, 38, 291.)
(q) Liao, G.; Wu, Y.-J.; Shi, B.-F. Acta Chim. Sinica 2020, 78, 289(in Chinese). (廖港, 吴勇杰, 史炳锋, 化学学报, 2020, 78, 289.)
(r) Yuan, Y.; Liang, Y.; Shi, S.; Liang, Y.-F.; Jiao, N. Chin. J. Chem. 2020, 38, 1245.
(s) Li, X.; Liang, G.; Shi, Z.-J. Chin. J. Chem. 2020, 38, 929.
For reviews, see: (a) Wang, F.; Yu, S.; Li, X. Chem. Soc. Rev. 2016, 45, 6462.
(b) Shah, T. A.; De, P. B.; Pradhan, S.; Banerjee, S.; Punniyamurthy, T. Chem.-Asian J. 2019, 14, 4520.
(a) Wang, H.; Lorion, M. M.; Ackermann, L. Angew. Chem., Int. Ed. 2017, 56, 6339.
(b) Lu, Q.; Klauck, F. J. R.; Glorius, F. Chem. Sci. 2017, 8, 3379.
Zhang, S.-S.; Wu, J.-Q.; Liu, X.; Wang, H. ACS Catal. 2015, 5, 210.
doi: 10.1021/cs501601c
For selected examples, see: (a) Yu, D.-G.; Suri, M.; Glorius, F. J. Am. Chem. Soc. 2013, 135, 8802.
(b) Wang, X.; Lerchen, A.; Glorius, F. Org. Lett. 2016, 18, 2090.
(c) Li, L.; Wang, H.; Yu, S.; Yang, X.; Li, X. Org. Lett. 2016, 18, 3662.
(d) Yang, X.; Jin, X.; Wang, C. Adv. Synth. Catal. 2016, 358, 2436.
(e) Gong, S.; Xi, W.; Ding, Z.; Sun, H. J. Org. Chem. 2017, 82, 7643.
(f) Wu, X.; Xiong, H.; Sun, S.; Cheng, J. Org. Lett. 2018, 20, 1396.
Wang, H.; Lorion, M. M.; Ackermann, L. ACS Catal. 2017, 7, 3430.
doi: 10.1021/acscatal.7b00756
(a) Lin, C.; Shen, L. ChemCatChem 2019, 11, 961.
(b) Lin, C.; Gao, F.; Shen, L. Adv. Synth. Catal. 2019, 361, 391.
(c) Lin, C.; Shen, L. RSC Adv. 2019, 9, 30650.
(d) Lin, J.; Guo, Z.; Lin, C.; Gao, F.; Shen, L. Chemistryselect 2020, 5, 1925.
(e) Lin, C.; Xu, Y.; Teng, Q.; Lin, J.; Gao, F.; Shen, L. Synlett 2020, 52, 889.
For selected examples of Ru(II)-catalyzed C-H activation, see: (a) Zheng, Q.-Z.; Liang, Y.-F.; Qin, C.; Jiao, N. Chem. Commun. 2013, 49, 5654.
(b) Kim, J.; Chang, S. Chem.-Eur. J. 2013, 19, 732.
(c) Mishra, A.; Vats, T. K.; Deb, I. J. Org. Chem. 2016, 81, 6525.
(d) Okada, T.; Nobushige, K.; Satoh, T.; Miura, M. Org. Lett. 2016, 18, 1150.
(e) Manikandana, R.; Jeganmohan, M. Chem. Commun. 2017, 53, 8931.
(f) More, N. Y.; Padala, K.; Jeganmohan, M. J. Org. Chem. 2017, 82, 12691.
(g) Kong, L.; Han, X.; Li, X. Chem. Commun. 2019, 55, 7339.
(h) Xu, W.; Wang, N.; Zhang, M.; Shi, D. Chin. J. Org. Chem. 2019, 39, 173(in Chinese). (徐文韬, 王宁, 张梦烨, 史达清, 有机化学, 2019, 39, 173.)
Yadav, V. K.; Babu, K. G. Eur. J. Org. Chem. 2005, 2005, 452.
doi: 10.1002/ejoc.200400591
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
Wenling Yuan , Fengli Li , Zhe Chen , Qiaoxin Xu , Zhenhua Guan , Nanyu Yao , Zhengxi Hu , Junjun Liu , Yuan Zhou , Ying Ye , Yonghui Zhang . AbnI: An α-ketoglutarate-dependent dioxygenase involved in brassicicene CH functionalization and ring system rearrangement. Chinese Chemical Letters, 2024, 35(5): 108788-. doi: 10.1016/j.cclet.2023.108788
Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp3)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
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
Yi Luo , Lin Dong . Multicomponent remote C(sp2)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp3)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647
Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C3N4/AgI.x.y heterojunction photocatalyst for simultaneous and stoichiometric production of H2 and H2O2 from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H2O2 Production and Cr(VI) Reduction over a Hierarchical Ti3C2/In4SnS8 Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
Peng Wang , Jianjun Wang , Ni Song , Xin Zhou , Ming Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF3·OEt2-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748
Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C3N4光催化剂及其高效H2O2光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C3N4纳米片用于高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp3)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
Jinpeng Du , Junlin Chen , Yulong Shan , Tongliang Zhang , Yu Sun , Zhongqi Liu , Xiaoyan Shi , Wenpo Shan , Yunbo Yu , Hong He . Insight into the effects of C3H6 on fresh and hydrothermally aged Cu-SSZ-39 catalysts. Chinese Chemical Letters, 2025, 36(3): 110019-. doi: 10.1016/j.cclet.2024.110019
Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C3N4纳米片及其高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019