Advances on the Merger of Electrochemistry and Transition Metal Catalysis for Organic Synthesis

被引:294
作者
Malapit, Christian A. [1 ]
Prater, Matthew B. [1 ]
Cabrera-Pardo, Jaime R. [1 ]
Li, Min [1 ]
Pham, Tammy D. [1 ]
McFadden, Timothy Patrick [1 ]
Blank, Skylar [1 ]
Minteer, Shelley D. [1 ]
机构
[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
C-H BONDS; CROSS-COUPLING REACTIONS; ANNULATIVE PI-EXTENSION; CARBON-CARBON BONDS; ARYL HALIDES; ANODIC-OXIDATION; ELECTROORGANIC CHEMISTRY; COBALT CATALYSIS; REDUCTIVE ELECTROCARBOXYLATION; ELECTROCATALYTIC OXIDATION;
D O I
10.1021/acs.chemrev.1c00614
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthetic organic electrosynthesis has grown in the past few decades by achieving many valuable transformations for synthetic chemists. Although electrocatalysis has been popular for improving selectivity and efficiency in a wide variety of energy-related applications, in the last two decades, there has been much interest in electrocatalysis to develop conceptually novel transformations, selective functionalization, and sustainable reactions. This review discusses recent advances in the combination of electrochemistry and homogeneous transition-metal catalysis for organic synthesis. The enabling transformations, synthetic applications, and mechanistic studies are presented alongside advantages as well as future directions to address the challenges of metal-catalyzed electrosynthesis.
引用
收藏
页码:3180 / 3218
页数:39
相关论文
共 353 条
[1]   Arene C-H bond activation and arene oxidative coupling by cationic palladium(II) complexes [J].
Ackerman, LJ ;
Sadighi, JP ;
Kurtz, DM ;
Labinger, JA ;
Bercaw, JE .
ORGANOMETALLICS, 2003, 22 (19) :3884-3890
[2]   Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations [J].
Ackermann, Lutz .
SYNLETT, 2007, (04) :507-526
[3]   Metalla-electrocatalyzed C-H Activation by Earth-Abundant 3d Metals and Beyond [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (01) :84-104
[4]   Cobalt-Catalyzed C-H Arylations, Benzylations, and Alkylations with Organic Electrophiles and Beyond [J].
Ackermann, Lutz .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19) :8948-8954
[5]   Cationic Ruthenium(II) Catalysts for Oxidative C-H/N-H Bond Functionalizations of Anilines with Removable Directing Group: Synthesis of Indoles in Water [J].
Ackermann, Lutz ;
Lygin, Alexander V. .
ORGANIC LETTERS, 2012, 14 (03) :764-767
[6]   Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].
Ackermann, Lutz .
CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345
[7]   Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage [J].
Ackermann, Lutz ;
Novak, Petr ;
Vicente, Ruben ;
Hofmann, Nora .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6045-6048
[8]   Catalytic Electrochemical C-H Iodination and One-Pot Arylation by ON/OFF Switching of Electric Current [J].
Aiso, Hiroko ;
Kochi, Takuya ;
Mutsutani, Hitoshi ;
Tanabe, Takamasa ;
Nishiyama, Shigeru ;
Kakiuchi, Fumitoshi .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17) :7718-7724
[9]   Enantioselective N-Alkylation of Indoles via an Intermolecular Aza-Wacker-Type Reaction [J].
Allen, Jamie R. ;
Bahamonde, Ana ;
Furukawa, Yukino ;
Sigman, Matthew S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (22) :8670-8674
[10]   CARBON-DIOXIDE AS A C1 BUILDING BLOCK - MECHANISM OF PALLADIUM-CATALYZED CARBOXYLATION OF AROMATIC HALIDES [J].
AMATORE, C ;
JUTAND, A ;
KHALIL, F ;
NIELSEN, MF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) :7076-7085