Recent advances in organic electrosynthesis employing transition metal complexes as electrocatalysts

被引:296
作者
Ma, Cong [1 ]
Fang, Ping [1 ]
Liu, Zhao-Ran [1 ]
Xu, Shi-Shuo [1 ]
Xu, Kun [2 ]
Cheng, Xu [3 ]
Lei, Aiwen [4 ]
Xu, Hai-Chao [5 ]
Zeng, Chengchu [2 ]
Mei, Tian-Sheng [1 ]
机构
[1] Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
[2] Beijing Univ Technol, Fac Environm & Life, Beijing 100124, Peoples R China
[3] Nanjing Univ, Sch Chem & Chem Engn, Jiangsu Key Lab Adv Organ Mat, Nanjing 210023, Peoples R China
[4] Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Stud, Wuhan 430072, Peoples R China
[5] Xiamen Univ, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China
基金
中国国家自然科学基金;
关键词
Organic electrosynthesis; Indirect electrolysis; Redox catalyst; Transition metal; Electrocatalyst; C-H FUNCTIONALIZATION; DEHYDROGENATIVE 3+2 ANNULATION; CROSS-COUPLING REACTIONS; ELECTROCHEMICAL SYNTHESIS; ANODIC-OXIDATION; NICKEL CATALYSIS; BOND ACTIVATION; PALLADIUM; ARYL; HALIDES;
D O I
10.1016/j.scib.2021.07.011
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Organic electrosynthesis has been widely used as an environmentally conscious alternative to conventional methods for redox reactions because it utilizes electric current as a traceless redox agent instead of chemical redox agents. Indirect electrolysis employing a redox catalyst has received tremendous attention, since it provides various advantages compared to direct electrolysis. With indirect electrolysis, overpotential of electron transfer can be avoided, which is inherently milder, thus wide functional group tolerance can be achieved. Additionally, chemoselectivity, regioselectivity, and stereoselectivity can be tuned by the redox catalysts used in indirect electrolysis. Furthermore, electrode passivation can be avoided by preventing the formation of polymer films on the electrode surface. Common redox catalysts include N-oxyl radicals, hypervalent iodine species, halides, amines, benzoquinones (such as DDQ and tetrachlorobenzoquinone), and transition metals. In recent years, great progress has been made in the field of indirect organic electrosynthesis using transition metals as redox catalysts for reaction classes including C-H functionalization, radical cyclization, and cross-coupling of aryl halides-each owing to the diverse reactivity and accessible oxidation states of transition metals. Although various reviews of organic electrosynthesis are available, there is a lack of articles that focus on recent research progress in the area of indirect electrolysis using transition metals, which is the impetus for this review. (c) 2021 Science China Press. Published by Elsevier B.V. and Science China Press. All rights reserved.
引用
收藏
页码:2412 / 2429
页数:18
相关论文
共 194 条
[11]   Nickel-Catalyzed Electrochemical Phosphorylation of Aryl Bromides [J].
Bai, Ya ;
Liu, Nian ;
Wang, Shutao ;
Wang, Siyu ;
Ning, Shulin ;
Shi, Lingling ;
Cui, Lili ;
Zhang, Zhuoqi ;
Xiang, Jinbao .
ORGANIC LETTERS, 2019, 21 (17) :6835-6838
[12]  
BAIZER MM, 1980, CHEMTECH, V10, P161
[13]   Recent advances in organometallic electrochemistry [J].
Battaglini, F ;
Calvo, EJ ;
Doctorovich, F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 547 (01) :1-21
[14]   C-H bond activation of benzene and methane by M(η2-O2CH)2 (M = Pd or Pt).: A theoretical study [J].
Biswas, B ;
Sugimoto, M ;
Sakaki, S .
ORGANOMETALLICS, 2000, 19 (19) :3895-3908
[15]   Coupling of Alternating Current to Transition-Metal Catalysis: Examples of Nickel-Catalyzed Cross-Coupling [J].
Bortnikov, Evgeniy O. ;
Semenov, Sergey N. .
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01) :782-793
[16]   Cobalt catalyzed electrochemical [4+2] annulation for the synthesis of sultams [J].
Cao, Yangmin ;
Yuan, Yong ;
Lin, Yueping ;
Jiang, Xiaomei ;
Weng, Yaqing ;
Wang, Tangwei ;
Bu, Faxiang ;
Zeng, Li ;
Lei, Aiwen .
GREEN CHEMISTRY, 2020, 22 (05) :1548-1552
[17]   Recent advances in transition metal-catalyzed asymmetric electrocatalysis [J].
Chakraborty, Priyanka ;
Mandal, Rajib ;
Garg, Nidhi ;
Sundararaju, Basker .
COORDINATION CHEMISTRY REVIEWS, 2021, 444
[18]   A molecular mediator for reductive concerted proton-electron transfers via electrocatalysis [J].
Chalkley, Matthew J. ;
Garrido-Barros, Pablo ;
Peters, Jonas C. .
SCIENCE, 2020, 369 (6505) :850-+
[19]   Asymmetric Electrochemical Transformations [J].
Chang, Xihao ;
Zhang, Qinglin ;
Guo, Chang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (31) :12612-12622
[20]   Asymmetric electrocarboxylation of 1-phenylethyl chloride catalyzed by electrogenerated chiral [COI(salen)]- complex [J].
Chen, Bao-Li ;
Zhu, Hong-Wei ;
Xiao, Yan ;
Sun, Qi-Long ;
Wang, Huan ;
Lu, Jia-Xing .
ELECTROCHEMISTRY COMMUNICATIONS, 2014, 42 :55-59