Electrocatalysis as an enabling technology for organic synthesis

被引:864
作者
Novaes, Luiz F. T. [1 ]
Liu, Jinjian [1 ]
Shen, Yifan [1 ]
Lu, Lingxiang [1 ]
Meinhardt, Jonathan M. [1 ]
Lin, Song [1 ]
机构
[1] Cornell Univ, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
关键词
RECYCLABLE ELECTROCHEMICAL ALLYLATION; TEMPO-MEDIATED ELECTROOXIDATION; ANODIC-OXIDATION PATHWAYS; ONE-POT SIMPLE; ARYL HALIDES; N-OXYL; H FUNCTIONALIZATION; CARBONYL-COMPOUNDS; COUPLING REACTIONS; ALCOHOL OXIDATION;
D O I
10.1039/d1cs00223f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Electrochemistry has recently gained increased attention as a versatile strategy for achieving challenging transformations at the forefront of synthetic organic chemistry. Electrochemistry's unique ability to generate highly reactive radical and radical ion intermediates in a controlled fashion under mild conditions has inspired the development of a number of new electrochemical methodologies for the preparation of valuable chemical motifs. Particularly, recent developments in electrosynthesis have featured an increased use of redox-active electrocatalysts to further enhance control over the selective formation and downstream reactivity of these reactive intermediates. Furthermore, electrocatalytic mediators enable synthetic transformations to proceed in a manner that is mechanistically distinct from purely chemical methods, allowing for the subversion of kinetic and thermodynamic obstacles encountered in conventional organic synthesis. This review highlights key innovations within the past decade in the area of synthetic electrocatalysis, with emphasis on the mechanisms and catalyst design principles underpinning these advancements. A host of oxidative and reductive electrocatalytic methodologies are discussed and are grouped according to the classification of the synthetic transformation and the nature of the electrocatalyst.
引用
收藏
页码:7941 / +
页数:63
相关论文
共 367 条
[81]   3d metallaelectrocatalysis for resource economical syntheses [J].
Gandeepan, Parthasarathy ;
Finger, Lars H. ;
Meyer, Tjark H. ;
Ackermann, Lutz .
CHEMICAL SOCIETY REVIEWS, 2020, 49 (13) :4254-4272
[82]   A simple and efficient approach to realize difunctionalization of arylketones with malonate esters via electrochemical oxidation [J].
Gao, Huihui ;
Zha, Zhenggen ;
Zhang, Zhenlei ;
Ma, Huanyue ;
Wang, Zhiyong .
CHEMICAL COMMUNICATIONS, 2014, 50 (39) :5034-5036
[83]  
Gao P.S., 2020, Angew. Chem, V132, P15366
[84]   Selective electrochemical C-O bond cleavage of β-O-4 lignin model compounds mediated by iodide ion [J].
Gao, Wei-Jing ;
Lam, Chiu Marco ;
Sun, Bao-Guo ;
Little, R. Daniel ;
Zeng, Cheng-Chu .
TETRAHEDRON, 2017, 73 (17) :2447-2454
[85]   Electrochemically Initiated Oxidative Amination of Benzoxazoles Using Tetraalkylammonium Halides As Redox Catalysts [J].
Gao, Wei-Jing ;
Li, Wei-Cui ;
Zeng, Cheng-Chu ;
Tian, Hong-Yu ;
Hu, Li-Ming ;
Little, R. Daniel .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (20) :9613-9618
[86]   Cobalt(II)-Catalyzed Electrooxidative C-H Amination of Arenes with Alkylamines [J].
Gao, Xinlong ;
Wang, Pan ;
Zeng, Li ;
Tang, Shan ;
Lei, Aiwen .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (12) :4195-4199
[87]   Deriving the Turnover Frequency of Aminoxyl-Catalyzed Alcohol Oxidation by Chronoamperometry: An Introduction to Organic Electrocatalysis [J].
Goes, Shannon L. ;
Mayer, Mikayla N. ;
Nutting, Jordan E. ;
Hoober-Burkhardt, Lena E. ;
Stahl, Shannon S. ;
Rafiee, Mohammad .
JOURNAL OF CHEMICAL EDUCATION, 2021, 98 (02) :600-606
[88]   Synthesis of unsymmetrical biaryls by electroreductive cobalt-catalyzed cross-coupling of aryl halides [J].
Gomes, P ;
Fillon, H ;
Gosmini, C ;
Labbé, E ;
Périchon, J .
TETRAHEDRON, 2002, 58 (42) :8417-8424
[89]   Electrochemical cross-coupling between 2-halopyridines and aryl or heteroaryl halides catalysed by nickel-2,2′-bipyridine complexes. [J].
Gosmini, C ;
Lasry, S ;
Nedelec, JY ;
Perichon, J .
TETRAHEDRON, 1998, 54 (07) :1289-1298
[90]   Electrochemical cross-coupling between functionalized aryl halides and 2-chloropyrimidine or 2-chloropyrazine catalyzed by nickel 2,2′-bipyridine complex [J].
Gosmini, C ;
Nédélec, JY ;
Périchon, J .
TETRAHEDRON LETTERS, 2000, 41 (02) :201-203