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 shu

Synthesis of Vinyl-Substituted Dihydroisoquinolone via Ru(Ⅱ)-Catalyzed C—H Functionalization/Annulation of Imidates

College of Chemistry and Chemical Engineering, Jiangxi Science & Technology Normal University, Nanchang 330013

Corresponding author: Lin Cong, conglin0127@jxstnu.com.cn Shen Liang, liangshen@jxstnu.com.cn
Received Date: 29 April 2020
Revised Date: 4 June 2020
Available Online: 19 June 2020
Fund Project: the Natural Science Foundation of Jiangxi Province 20202BABL213005the National Natural Science Foundation of China 21704036Project supported by the National Natural Science Foundation of China (Nos. 51963010, 21704036) and the Natural Science Foundation of Jiangxi Province (No. 20202BABL213005)the National Natural Science Foundation of China 51963010

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An efficient and powerful approach for the construction of vinyl-substituted dihydroisoquinolone derivatives through ruthenium-catalyzed tandem C—H functionalization/annulation of imidates has been demonstrated. Various substituted functional groups of imidates could be well tolerated in this new transformation, delivering the corresponding products in moderate to good yields. This method represents the first successful example of Ru(Ⅱ)-catalyzed C—H functionalization/an-nulation of imidates with 4-vinyl-1, 3-dioxolan-2-one to the efficient synthesis of 3-vinyl-3, 4-dihydroisoquinolin-1(2H)-ones.
- vinyl-substituted dihydroisoquinolone,
- ruthenium-catalysis,
- C-H functionalization,
- imidate,
- 4-vinyl-1, 3-di-oxolan-2-one
1. [1]
  (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.
2. [2]
  (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.
3. [3]
  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.
4. [4]
  (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.
5. [5]
  Zhang, S.-S.; Wu, J.-Q.; Liu, X.; Wang, H. ACS Catal. 2015, 5, 210. doi: 10.1021/cs501601c
6. [6]
  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.
7. [7]
  Wang, H.; Lorion, M. M.; Ackermann, L. ACS Catal. 2017, 7, 3430. doi: 10.1021/acscatal.7b00756
8. [8]
  (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.
9. [9]
  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.)
10. [10]
  Yadav, V. K.; Babu, K. G. Eur. J. Org. Chem. 2005, 2005, 452. doi: 10.1002/ejoc.200400591
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  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
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15. [15]
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17. [17]
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19. [19]
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