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

Figures(5)

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
1. [1]
  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]
  Xin-Juan Wang , Yao-Hang Cheng , Xin-Yan Lv , Li-Ye Liang , Guang-Hui An , Guang-Ming Li . Ruthenium-catalyzed alkylarylation of alkenes via para-selective C-H functionalization of unprotected anilines. Chinese Chemical Letters, 2026, 37(8): 112154-. doi: 10.1016/j.cclet.2025.112154
4. [4]
  Huai-Gui Li , Can-Ming Zhu , Weidong Yuan , Hongyi Chen , Zhengyuan Bo , Chao Deng , Yingguang Zhu , Kang Chen , Qing-Yuan Meng . Stereodivergent reductive C(sp²)-C(sp³) coupling between cycloketone oximes and vinyl halides enabled by tunable photoredox/Ti dual catalysis. Chinese Chemical Letters, 2026, 37(7): 111941-. doi: 10.1016/j.cclet.2025.111941
5. [5]
  Mengyao Yuan , Wansen Xie , Xiaoyu Yang . Enantioselective synthesis of inherently chiral calix[4]arenes via asymmetric C-H bromination of phenols. Chinese Chemical Letters, 2026, 37(9): 112157-. doi: 10.1016/j.cclet.2025.112157
6. [6]
  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
7. [7]
  Xiao-Hua Chen , Yifan Fan , Zitong Wu , Tao Tu . Non-canonical bio-inspired iron catalysis for aliphatic C–H functionalization. Chinese Chemical Letters, 2026, 37(3): 112132-. doi: 10.1016/j.cclet.2025.112132
8. [8]
  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
9. [9]
  Yongli Zhao , Dingsheng Cao , Jie-Ping Wan , Yunyun Liu . Synthesis of 3-phosphinyl chromones via in situ iodination mediated C-H phosphination and the tunable synthesis of 2-phosphoryl chromanones. Chinese Chemical Letters, 2026, 37(1): 111740-. doi: 10.1016/j.cclet.2025.111740
10. [10]
  Da-Qiu Cui , Quan-Xin Li , Jia-Bo Huang , Ying-Qi Zhang , Xuan Wang , Shao-Fei Ni , Long-Wu Ye , Bo Zhou . Atroposelective transformation of vinyl cations by chiral Brønsted acid catalysis. Chinese Chemical Letters, 2026, 37(6): 111738-. doi: 10.1016/j.cclet.2025.111738
11. [11]
  Dingding Xia , Chundong Huang , Zhimin Hu , Zhiyong Leng , Miaomiao Zhuo , Shoubhik Das , Shaofei Ni , Yu Zhang , Weidong Zhang . Tandem N–H insertion/C–H functionalization-S_N1 reaction to access unnatural amino esters and the concise synthesis of Streptindole and Arsindoline B. Chinese Chemical Letters, 2026, 37(10): 112224-. doi: 10.1016/j.cclet.2025.112224
12. [12]
  Junhua Li , Yu Fu , Yian Shi . A rapid access to fused polycyclic indolo[2,1-a]isoquinolins via Pd-catalyzed sequential Heck/C-H activation/amination reaction with diaziridinone. Chinese Chemical Letters, 2026, 37(3): 111376-. doi: 10.1016/j.cclet.2025.111376
13. [13]
  Weimei Zeng , Youai Qiu . Electrochemical C-H carboxylation of benzylamines. Chinese Chemical Letters, 2026, 37(1): 111679-. doi: 10.1016/j.cclet.2025.111679
14. [14]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  Xin-Han Wang , Ying Huang , Chun-Lin Zhang , Song Ye . γ-C(sp³)-H acylation of aliphatic amines enabled by cooperative photoredox NHC/Pd catalysis. Chinese Chemical Letters, 2026, 37(5): 111484-. doi: 10.1016/j.cclet.2025.111484
18. [18]
  Xinghao Cai , Chen Ma , Ying Kang , Yuqiang Ren , Xue Meng , Wei Lu , Shiming Fan , Shouxin Liu . Nickel-catalyzed C(sp²)–H alkynylation of free α-substituted benzylamines using a transient directing group. Chinese Chemical Letters, 2025, 36(10): 110901-. doi: 10.1016/j.cclet.2025.110901
19. [19]
  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
20. [20]
  Xin Zhou , Guangyao Liu , Meifang Yang , Mengyu Li , Xiaodi Yang , Weiliang Gu , Yitian Zhao , Houchao Tao . Glycosyl N-phenyl pentafluorobenzimidates as a new generation of imidate donors for catalytic glycosylation. Chinese Chemical Letters, 2025, 36(8): 110734-. doi: 10.1016/j.cclet.2024.110734

Get Citation

PDF

XML

Metrics

PDF Downloads(6)
Abstract views(1597)
HTML views(234)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142