Chinese Journal of Organic Chemistry >
Progress in the Synthesis of Pyrrole-2-carboxylate Catalyzed by Transition Metals
Received date: 2020-06-23
Revised date: 2020-08-10
Online published: 2020-08-31
Supported by
the National Natural Science Foundation of China(21901124); the Natural Science Foundation of the Jiangsu Higher Education Institutions(19KJB150032)
Pyrrole-2-carboxylates exist widely in biologically active molecules and have many important applications in the field of medicine. Therefore, the synthesis of pyrrole-2-carboxylates has received extensive attention. The transition metal- catalyzed cycloaddition reactions are widely used in the synthesis of pyrrole skeletons and have the advantages of regio- selectivity. The formation methods of C—N bonds directed by transition metal ligand have some advantages, such as milder reaction conditions, higher atomic step economy, efficiency and selectivity. The reactions of [3+2], [4+1] and [2+2+1] cycloaddition are reviewed, and the reaction mechanism and application of pyrrole-2-carboxylate compounds are introduced under various transition-metal conditions. The prospects of the synthesis of pyrrole-2-carboxylates are also discussed.
Ci Li , Mingrui Li , Yuxing Xie , Yang Yu , Fei Huang . Progress in the Synthesis of Pyrrole-2-carboxylate Catalyzed by Transition Metals[J]. Chinese Journal of Organic Chemistry, 2021 , 41(2) : 594 -610 . DOI: 10.6023/cjoc202006048
| [1] | Xu W. M.S. Thesis, Wenzhou University, Wenzhou, 2017. (in Chinese) |
| [1] | 徐薇, 硕士论文, 温州大学, 温州, 2017.). |
| [2] | Walsh C.T.; Garneau-Tsodikova S.; Howard-Jones A.R. Nat. Prod. Rep. 2006, 23, 517. |
| [3] | Zhao K.; Wang S.; Zhan X.P.; Liu Z.L.; Mao Z.M. Chin. J. Org. Chem. 2017, 37, 945. (in Chinese) |
| [3] | 赵凯, 王帅, 詹晓平, 刘增路, 毛振民, 有机化学, 2017, 37, 945.). |
| [4] | Young I.S.; Thornton P.D.; Thompson A. Nat. Prod. Rep. 2010, 27, 1801. |
| [5] | Fr?de R.; Hinze C.; Josten I.; Schmidt B.; Steffan B.; Steglich W. Tetrahedron Lett. 1994, 35, 1689. |
| [6] | Cong W.; Wang L.; Yu F.; Li J. Chin. J. Org. Chem. 2018, 38, 2866. (in Chinese) |
| [6] | 丛文霞, 王莉, 于福强, 李纪兴, 有机化学, 2018, 38, 2866.). |
| [7] | Shao C.W. Ph.D. Dissertation, Tsinghua University, Beijing, 2010. (in Chinese) |
| [7] | 韶长伟, 博士论文, 清华大学, 北京, 2010.). |
| [8] | Chen X. Ph.D. Dissertation, South China University of Technology, Guangzhou, 2017. (in Chinese) |
| [8] | 陈训, 博士论文, 华南理工大学, 广州, 2017.). |
| [9] | Jiang B. Ph.D. Dissertation, University of Science and Technology of China, Hefei, 2018. (in Chinese) |
| [9] | 姜兵, 博士论文, 中国科学技术大学, 合肥, 2018.). |
| [10] | Hynes J.; Dychman A.J.; Lin S.; Wrobleski S.T.; Wu H.; Cillooly K.M.; Kanner S.B.; Lonial H.; Loo D.; McIntyre K.W.; Pitt S.; Shen D.R.; Shuster D.J.; Yang X.X.; Zhang R.; Behnia K.; Zhang H.J.; Marathe P.H.; Doweyko A.M.; Tokarski J.S.; Sack J.S.; Pokross M.; Kiefer S.E.; Newitt J.A.; Barrish J.C.; Dodd J.; Schieven G.L.; Leftheris K. J. Med. Chem. 2008, 51, 6. |
| [11] | Paal C. Chem. Ber. 1885, 18, 367. |
| [12] | Banik B.K.; Banik I.; Renteria M.; Dasgupta S.K. Tetrahedron Lett. 2005, 46, 2643. |
| [13] | Hantzsch A. Ber. Dtsch. Chem. Ges. 1890, 23, 1474. |
| [14] | Zhang J.G.; Wu Z.X.; Xie F.; Zhang W.B. Chin. J. Org. Chem. 2018, 38, 1319. (in Chinese) |
| [14] | 张金刚, 吴正兴, 谢芳, 张万斌, 有机化学, 2018, 38, 1319.). |
| [15] | (a) Fogg D.E.; dos Santos, E.N.Coord. Chem. Rev. 2004, 248, 2365. |
| [15] | (b) Ajamian A.; Gleason J.L. Angew. Chem., Int. Ed. 2004, 116, 3842. |
| [15] | (c) Ajamian A.; Gleason J.L. Angew. Chem., Int. Ed. 2004, 43, 3754. |
| [16] | Yin H.; Wang L.; Chen J.; Li H.; Ma W.; Li Z.; Li Y. Modern. Chem. Res. 2018, 143. (in Chinese) |
| [16] | 尹浩, 王露露, 陈家威, 李呼努, 马威, 李志忠, 李怡, 当代化工研究, 2018, 143.). |
| [17] | Lopez-Perez A.; Robles-Machin R.; Adrio J.; Carretero J.C. Angew. Chem., Int. Ed. 2007, 46, 9261. |
| [18] | Robles-Machin R.; Gonzalez E.M.; Adrio J.; Carretero J.C. J. Org. Chem. 2010, 75, 233. |
| [19] | Zhou N.N.; Xie T.; Liu L.; Xie Z.X. J. Org. Chem. 2014, 79, 6061. |
| [20] | Zhu J.N.; Chen L.L.; Zhou R.X.; Li B.; Shao Z.Y.; Zhao S.Y. Org. Lett. 2017, 19, 6044. |
| [21] | Chiba S.; Wang Y.F.; Lapointe G.; Narasaka K. Org. Lett. 2008, 10, 313. |
| [22] | Zhang L.; Wang X.B.; Li S.Y.; Wu J. Tetrahedron 2013, 69, 3805. |
| [23] | Kamijo S.; Kanazawa C.; Yamamoto Y. J. Am. Chem. Soc. 2005, 127, 9260. |
| [24] | Li M.R.; Sun Y.M.; Xie Y.X.; Yu Y.; Huang F.; Huang H. Chem. Commun. 2020, 56, 11050. |
| [25] | Wu S.; Xiong X.D.; Wang S.G. Rare Met. 2007, 31, 237. (in Chinese) |
| [25] | 吴松, 熊晓东, 王胜国, 稀有金属, 2007, 31, 237.). |
| [26] | Zou Y.Q.; Lu L.Q.; Fu L.; Chang N.J.; Rong J.; Chen J.R.; Xiao W.J. Angew. Chem., Int. Ed. 2011, 50, 7171. |
| [27] | Padwa A.; Stengel T. Tetrahedron Lett. 2004, 45, 5991. |
| [28] | Shang Y.W.; Cheng R.J.; Liu W.Z.; Dou L.J. Mod. Salt Chem. Ind. 2019, 46, 51. (in Chinese) |
| [28] | 尚英伟, 程瑞姣, 刘文竹, 豆立娟, 现代盐化工, 2019, 46, 51.). |
| [29] | Sahani R.L.; Liu R.S. Angew. Chem., Int. Ed. 2016, 55, 1. |
| [30] | Du X.W.; Xie X.; Liu Y.H. J. Org. Chem. 2010, 75, 510. |
| [31] | Tro?mov B.A.; Mikhaleva A.I. Heterocycles 1994, 37, 1193. |
| [32] | Ngwerume S.; Camp J.E. Chem. Commun. 2011, 47, 1857. |
| [33] | Liu Y.; Hu H.Y.; Wang X.; Zhi S.J.; Kan Y.H.; Wang C. J. Org. Chem. 2017, 82, 4194. |
| [34] | Kudryavtsev K.V.; Ivantcova P.M.; Churakov A.V.; Vasin V.A. Tetrahedron Lett. 2012, 53, 4300. |
| [35] | Liu W.B.; Jiang H.F.; Huang L.B. Org. Lett. 2010, 12, 312. |
| [36] | Liao J.Y.; Shao P.L.; Zhao Y. J. Am. Chem. Soc. 2015, 137, 628. |
| [37] | Luo K.X.; Mao S.; He K.; Yu X.L.; Pan J.H.; Lin J.; Shao Z.H.; Jin Y. ACS Catal. 2020, 10, 3733. |
| [38] | Chen Y.Y.; Mao G.L.; Liu X.B.; Wu W. Chem. Reagents 2018, 40, 913. (in Chinese) |
| [38] | 陈莹莹, 毛国梁, 刘小兵, 吴韦, 化学试剂, 2018, 40, 913.). |
| [39] | Wang Y.L.; Zhu S.Z. Org. Lett. 2003, 5, 745. |
| [40] | Dong H.J.; Shen M.H.; Redford J.E.; Stokes B.J.; Pumphrey A.L.; Driver T.G. Org. Lett. 2007, 9, 5191. |
| [41] | Takaya H.; Kojima S.; Murahashi S.I. Org. Lett. 2001, 3, 421. |
| [42] | Zhang H.M.; Li L.Z.; Shen F, Q.; Cai, T.; Shen, R.B.Chin. J. Org. Chem. 2020, 40, 873. (in Chinese) |
| [42] | 张慧苗, 李灵芝, 沈方旗, 蔡涛, 沈润溥, 有机化学, 2020, 40, 873.). |
| [43] | Esteeves C. H. A.; Koyioni M.; Christensen K.E.; Smith P.D.; Donohoe T.J. Org. Lett. 2018, 20, 4048. |
| [44] | Crawley M.L.; Goljer I.; Jenkins D.J.; Mehlmann J.F.; Nogle L.; Dooley R.; Mahaney P.E. Org. Lett. 2006, 8, 5837. |
| [45] | Queiroz M.; Begouin A.; Pereira G.; Ferreira P. Tetrahedron 2008, 64, 10714. |
| [46] | Cheng G.; Yang D.Q. Chin. J. Org. Chem. 2015, 35, 2023. (in Chinese) |
| [46] | 程果, 杨定乔, 有机化学, 2015, 35, 2023.). |
| [47] | Hiroya K.; Matsumoto S.; Ashikawa M.; Ogiwara K.; Sakamoto T. Org. Lett. 2006, 8, 5349. |
| [48] | Chen Y. Ph.D. Dissertation, Zhejiang University of Technology, Hangzhou, 2015. (in Chinese) |
| [48] | 陈勇, 博士论文, 浙江工业大学, 杭州, 2015.). |
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