Advances in Asymmetric Organotransition Metal-Catalyzed Electrochemistry
- Corresponding author: Fang Ping, pfang@sioc.ac.cn Mei Tiansheng, mei7900@sioc.ac.cn
Citation:
Wang Xiangyang, Xu Xuetao, Wang Zhenhua, Fang Ping, Mei Tiansheng. Advances in Asymmetric Organotransition Metal-Catalyzed Electrochemistry[J]. Chinese Journal of Organic Chemistry,
;2020, 40(11): 3738-3747.
doi:
10.6023/cjoc202003022
Kolbe, H. J. Prakt. Chem. 1847, 41, 137.
doi: 10.1002/prac.18470410118
Baizer, M. M. J. Electrochem. Soc. 1964, 111, 215.
doi: 10.1149/1.2426086
(a) Wang, F.; Stahl, S. S. Acc. Chem. Res. 2020, 53, 561.
(b) Siu, J. C.; Fu, N.; Lin, S. Acc. Chem. Res. 2020, 53, 547.
(c) Fuchigami, T.; Inagi, S. Acc. Chem. Res. 2020, 53, 322.
(d) Flexer, V.; Jourdin, L. Acc. Chem. Res. 2020, 53, 311.
(e) Jiao, K.-J.; Xing, Y.-K.; Yang, Q.-L.; Qiu, H.; Mei, T.-S. Acc. Chem. Res. 2020, 53, 300.
(f) Robinson, S.; Sigman, M. S. Acc. Chem. Res. 2020, 53, 289.
(g) Jing, Q.; Moeller, K. D. Acc. Chem. Res. 2020, 53, 135.
(h) Leech, M. C.; Lam, K. Acc. Chem. Res. 2020, 53, 121.
(i) Yamamoto, K.; Kuriyama, M.; Onomura, O. Acc. Chem. Res. 2020, 53, 105.
(j) Ackermann, L. Acc. Chem. Res. 2020, 53, 84.
(k) Kingston, C.; Palkowitz, M. D.; Takahira, Y.; Vantourout, J. C.; Peters, B. K.; Kawamata, Y.; Baran, P. S. Acc. Chem. Soc. 2020, 53, 72.
(l) Röckl, J. L.; Pollok, D.; Franke, R.; Waldvogel, S. R. Acc. Chem. Res. 2020, 53, 45.
(m) Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52, 3339.
(n) Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52, 3309.
(o) Jiang, Y.; Xu, K.; Zeng, C. Chem. Rev. 2018, 118, 4485.
(p) Yang, Q.-L.; Fang, P.; Mei, T.-S. Chin. J. Chem. 2018, 36, 338.
(q) Ma, C.; Fang, P.; Mei, T.-S. ACS Catal. 2018, 8, 7179.
(r) Karkas, M. D. Chem. Soc. Rev. 2018, 47, 5786.
(s) Horn, E. J.; Rosen, B. R.; Baran, P. S. ACS Cent. Sci. 2016, 2, 302.
(a) Hou, Z.-W.; Xu, H.-C. Chin. J. Chem. 2020, 38, 394.
(b) Ye, Z.; Zhang, F. Chin. J. Org. Chem. 2020, 40, 241 (in Chinese).
(叶增辉, 张逢质, 有机化学, 2020, 40, 241.)
(c) Qian, X.-Y.; Xiong, P.; Xu, H.-C. Acta Chim. Sinica 2019, 77, 879 (in Chinese).
(钱向阳, 熊鹏, 徐海超, 化学学报, 2019, 77, 879.)
(d) Yang, Q.-L.; Wang, X.-Y.; Weng, X.-J.; Yang, X.; Xu, X.-T.; Tong, X.; Fang, P.; Wu, X.-Y.; Mei, T.-S. Acta Chim. Sinica 2019, 77, 866 (in Chinese).
(杨启亮, 王向阳, 翁信军, 杨祥, 徐学涛, 童晓峰, 方萍, 伍新燕, 梅天胜, 化学学报, 2019, 77, 866.)
(e) Zhang, H. Tang, R.; Shi, X.; Xie, L.; Wu, J. Chin. J. Org. Chem. 2019, 39, 1837 (in Chinese).
(张怀远, 唐蓉萍, 石星丽, 颉林, 伍家卫, 有机化学, 2019, 39, 1837.)
(f) Feng, E.-Q.; Hou, Z.-W.; Xu, H.-C. Chin. J. Org. Chem. 2019, 39, 1424 (in Chinese).
(冯恩祺, 侯中伟, 徐海超, 有机化学, 2019, 39, 1424.)
(g) Zhou, Z.; Yuan, Y.; Cao, Y.; Qiao, J.; Yao, A.; Zhao, J.; Zou, W. Chen, W.; Lei, A. Chin. J. Chem. 2019, 37, 611.
(h) Lu, F.; Yang, Z.; Wang, T.; Wang, T.; Zhang, Y.; Yuan, Y.; Lei, A. Chin. J. Chem. 2019, 37, 547.
(i) Hou, Z.-W.; Yan, H.; Song, J.; Xu, H.-C. Chin. J. Chem. 2018, 36, 909.
(j) Wu, Y.; Xi, Y.; Zhao, M.; Wang, S. Chin. J. Org. Chem. 2018, 38, 2590 (in Chinese).
(吴亚星, 席亚超, 赵明, 王思懿, 有机化学, 2018, 38, 2590.)
(a) Chang, X.; Zhang, Q.; Guo, C. Angew. Chem., Int. Ed. 2020, 59, 12612.
(b) Ghosh, M.; Shinde, V. S.; Rueping, M. Beilstein J. Org. Chem. 2019, 15, 2710.
(c) Lin, Q.; Li, L.; Luo, S. Chem. Eur. J. 2019, 25, 10033.
Seebach, D.; Oei, H. A. Angew. Chem., Int. Ed. 1975, 14, 634.
(a) Louafi, F.; Moreau, J.; Shahane, S.; Golhen, S.; Roisnel, T.; Sinbandhit, S.; Hurvois, J.-P. J. Org. Chem. 2011, 76, 9720.
(b) Feroci, M.; Inesi, A.; Orsini, M.; Palombi, L. Org. Lett. 2002, 4, 2617.
(a) Kodama, Y.; Fujiwara, A.; Kawamoto, H.; Ohta, N.; Kitani, A.; lto, S. Chem. Lett. 2001, 30, 240.
(b) Horner, L.; Degner, D. Tetrahedron Lett. 1971, 12, 1241.
(a) Shiigi, H.; Mori, H.; Tanaka, T.; Demizu, Y.; Onomura, O. Tetrahedron Lett. 2008, 49, 5247.
(b) Kuroboshi, M.; Yoshihisa, H.; Cortona, M. N.; Kawakami, Y.; Gao, Z.; Tanaka, H. Tetrahedron Lett. 2000, 41, 8131.
(c) Kashiwagi, Y.; Kurashima, F.; Kikuchi, C.; Anzai, J.; Osa, T.; Bobbitt, J. M. Chem. Commun. 1999, 1983.
(a) Kashiwagi, Y.; Kurashima, F.; Chiba, S.; Anzai, J.; Osa, T.; Bobbitt, J. M. Chem. Commun. 2003, 114.
(b) Moutet, J. C.; Duboc-Toia, C.; Ménage, S.; Tingry, S. Adv. Mater. 1998, 10, 665.
(c) Komori, T.; Nonaka, T. J. Am. Chem. Soc. 1984, 106, 2656.
(d) Firth, B. E.; Miller, L. L. J. Am. Chem. Soc. 1976, 98, 8272.
(e) Watkins, B. F.; Behling, J. R.; Kariv, E.; Miller, L. L. J. Am. Chem. Soc. 1975, 97, 3549.
Gourley, R. N.; Grimshaw, J.; Millar, P. G. Chem. Commun. 1967, 1278.
(a) Kobayashi, S.; Sugiura, M. Adv. Synth. Catal. 2006, 348, 1496.
(b) Lohray, B. B. Tetrahedron: Asymmetry 1992, 3, 1317.
(a) Sugimoto, H.; Kitayama, K.; Mori, S.; Itoh, S. J. Am. Chem. Soc. 2012, 134, 19270.
(b) Metin, O.; Alp, N. A.; Akbayrak, S.; Bicer, A.; Gultekin, M. S.; Ozkar, S.; Bozkaya, U. Green Chem. 2012, 14, 1488.
(c) Sugimoto, H.; Kitayama, K.; Mori, S.; Itoh, S. J. Am. Chem. Soc. 2012, 134, 19270.
(a) Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2024.
(b) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
(c) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974.
Amundsen, R.; Balko, E. N. Appl. J. Electrochem. 1992, 22, 810.
doi: 10.1007/BF01023722
Torii, S.; Liu, P.; Tanaka, H. Chem. Lett. 1995, 24, 319.
doi: 10.1246/cl.1995.319
Torii, S.; Liu, P.; Bhuvaneswari, N.; Amatore, C.; Jutand, A. J. Org. Chem. 1996, 61, 3055.
doi: 10.1021/jo952137r
Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
Guo, P.; Wong, K.-Y. Electrochem. Commun. 1999, 1, 559.
doi: 10.1016/S1388-2481(99)00110-1
Tanaka, H.; Kuroboshi, M.; Takeda, H.; Kanda, H.; Torii, S. J. Electroanal. Chem. 2001, 507, 75.
doi: 10.1016/S0022-0728(01)00387-4
Fu, N.; Song, L.; Liu, J.; Shen, Y.; Siu, J. C.; Lin, S. J. Am. Chem. Soc. 2019, 141, 14480.
doi: 10.1021/jacs.9b03296
Minato, D.; Arimoto, H.; Nagasue, Y.; Demizu, Y.; Onomura, O. Tetrahedron. 2008, 64, 6675.
doi: 10.1016/j.tet.2008.05.015
Onomura, O.; Arimoto, H.; Matsumura, Y.; Demizu, Y. Tetrahedron Lett. 2007, 48, 8668.
doi: 10.1016/j.tetlet.2007.10.014
Shono, T.; Hamaguchi, H.; Matsumura, Y. J. Am. Chem. Soc. 1975, 97, 4264.
doi: 10.1021/ja00848a020
(a) Jones, A. M.; Banks, C. E. Beilstein J. Org. Chem. 2014, 10, 3056.
(b) Onomura, O. Heterocycles 2012, 85, 2111.
(c) Shono, T. Top. Curr. Chem. 1988, 148, 1.
Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.
doi: 10.1021/acs.chemrev.7b00397
(a) D'Oca, M. G. M.; Pilli, R. A.; Pardini, V. L.; Curi, D.; Comni- nos, F. C. M. J. Braz. Chem. Soc. 2001, 12, 507.
(b) Sierecki, E.; Errasti, G.; Martens, T.; Royer, J. Tetrahedron 2010, 66, 10002.
(c) Lee, D.-S. Tetrahedron: Asymmetry 2009, 20, 2014.
(d) Shankaraiah, N.; Pilli, R. A.; Santos, L. S. Tetrahedron Lett. 2008, 5098.
(e) Zelgert, M.; Nieger, M.; Lennartz, M.; Steckhan, E. Tetrahedron 2002, 58, 2641.
(f) Matsumura, Y.; Kanda, Y.; Shirai, K.; Onomura, O.; Maki, T. Tetrahedron 2000, 56, 7411.
Fu, N.; Li, L.; Yang, Q.; Luo, S. Org. Lett. 2017, 19, 2122.
doi: 10.1021/acs.orglett.7b00746
Gao, P.-S.; Weng, X.-J.; Wang, Z.-H.; Zheng, C.; Sun, B.; Chen, Z.-H.; You, S.-L.; Mei, T.-S. Angew. Chem., Int. Ed. 2020, 59, 15254.
doi: 10.1002/anie.202005099
(a) Lennox, A. J. J.; Geos, S. L.; Webster, M. P.; Koolman, H. F.; Djuric, S. W.; Stahl, S. S. J. Am. Chem. Soc. 2018, 140, 11227.
(b) Wang, F.; Rafiee, M.; Stahl, S. S. Angew. Chem., Int. Ed. 2018, 57, 6686.
(c) Wu, Y.; Yi, H.; Lei, A. ACS Catal. 2018, 8, 1192.
(d) Li, C.; Zeng, C.-C.; Hu, L.-M.; Yang, F.-L.; Yoo, S. J.; Little, R. D. Electrochim. Acta 2013, 114, 560.
(e) Cao, Y.; Suzuki, K.; Tajima, T.; Fuchigami, T. Tetrahedron 2005, 6854.
Ryan, M. C.; Whitemire, L. D.; Mccann, S. D.; Stahl, S. S. Inorg. Chem. 2019, 58, 10194.
doi: 10.1021/acs.inorgchem.9b01326
Badalyan, A.; Stahl, S. S. Nature 2016, 535, 406.
doi: 10.1038/nature18008
Huang, X.; Zhang, Q.; Lin, J.; Harms, K.; Meggers, E. Nat. Catal. 2019, 2, 34.
doi: 10.1038/s41929-018-0198-y
Zhang, Q.; Chang, X.; Peng, L.; Guo, C. Angew. Chem., Int. Ed. 2019, 58, 6999.
doi: 10.1002/anie.201901801
Lu, P.; Jackson, J. J.; Eickhoff, J. A.; Zakarian, A. J. Am. Chem. Soc. 2015, 137, 656.
doi: 10.1021/ja512213c
Dhawa, U.; Tian, C.; Wdowik, T.; Oliveira, J. C. A.; Hao, J.; Ackermann, L. Angew. Chem., Int. Ed. 2020, 59, 13451.
doi: 10.1002/anie.202003826
Chen, B.-L.; Zhu, H.-W.; Xiao, Y.; Sun, Q.-L.; Wang, H.; Lu, J.-X. Electrochem. Commun. 2014, 42, 55.
doi: 10.1016/j.elecom.2014.02.009
Jiao, K.-J.; Li, Z.-M.; Xu, X.-T.; Zhang, L.-P.; Li, Y.-Q.; Zhang, K.; Mei, T.-S. Org. Chem. Front. 2018, 5, 2244.
doi: 10.1039/C8QO00507A
Franco, D.; Riahi, A.; Hénin, F.; Muzart, J.; Duñach, E. Eur. J. Org. Chem. 2002, 2257.
DeLano, T. J.; Reisman, S. E. ACS Catal. 2019, 9, 6751.
doi: 10.1021/acscatal.9b01785
Qiu, H.; Shuai, B.; Wang, Y.-Z.; Liu, D.; Chen, Y.-G.; Gao, P.-S.; Ma, H.-X.; Chen, S.; Mei, T.-S. J. Am. Chem. Soc. 2020, 142, 9872.
doi: 10.1021/jacs.9b13117
Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
Jieshuai Xiao , Yuan Zheng , Yue Zhao , Zhuangzhi Shi , Minyan Wang . Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis. Chinese Chemical Letters, 2025, 36(5): 110243-. doi: 10.1016/j.cclet.2024.110243
Ke QIAO , Yanlin LI , Shengli HUANG , Guoyu YANG . Advancements in asymmetric catalysis employing chiral iridium (ruthenium) complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2091-2104. doi: 10.11862/CJIC.20240265
Xiang Huang , Dongzhen Xu , Yang Liu , Xia Huang , Yangfan Wu , Dongmei Fang , Bing Xia , Wei Jiao , Jian Liao , Min Wang . Asymmetric synthesis of difluorinated α-quaternary amino acids (DFAAs) via Cu-catalyzed difluorobenzylation of aldimine esters. Chinese Chemical Letters, 2024, 35(12): 109665-. doi: 10.1016/j.cclet.2024.109665
Tengfei Xuan , Yuan Pan , Zhenyu Shi , Yang Wang . Organocatalytic asymmetric synthesis of oxazolines from N-acylimines. Chinese Chemical Letters, 2025, 36(6): 110352-. doi: 10.1016/j.cclet.2024.110352
Yanxin Jiang , Kwai Wun Cheng , Zhiping Yang , Jun (Joelle) Wang . Pd-catalyzed enantioselective and regioselective asymmetric hydrophosphorylation and hydrophosphinylation of enynes. Chinese Chemical Letters, 2025, 36(5): 110231-. doi: 10.1016/j.cclet.2024.110231
Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C6F5)3/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
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
Guang Xu , Cuiju Zhu , Xiang Li , Kexin Zhu , Hao Xu . Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones. Chinese Chemical Letters, 2025, 36(4): 110114-. doi: 10.1016/j.cclet.2024.110114
Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
Guoying Han , Qazi Mohammad Junaid , Xiao Feng . Topology-driven directed synthesis of metal-organic frameworks. Chinese Journal of Structural Chemistry, 2025, 44(3): 100447-100447. doi: 10.1016/j.cjsc.2024.100447
Zhirong Yang , Shan Wang , Ming Jiang , Gengchen Li , Long Li , Fangzhi Peng , Zhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518
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
Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
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
Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830
Ya-Ling Li , Jia-Wei Ke , Yue Liu , Dong-Mei Yao , Jing-Dong Zhang , You-Cai Xiao , Fen-Er Chen . Asymmetric conjugated addition of aryl Grignard reagents for the construction of chromanones bearing quaternary stereogenic centers in batch and flow. Chinese Chemical Letters, 2025, 36(6): 110377-. doi: 10.1016/j.cclet.2024.110377
Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301