Electrochemical Oxidative Cross-coupling with Hydrogen Evolution: A Green and Sustainable Way for Bond Formation

被引：670

作者：

Tang, Shan ^{[1
]}

Liu, Yichang ^{[1
]}

Lei, Aiwen ^{[1
,2
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Inst Adv Studies, Wuhan 430072, Hubei, Peoples R China

[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China

来源：

CHEM | 2018年 / 4卷 / 01期

基金：

中国国家自然科学基金;

关键词：

ORGANOCATALYZED ANODIC-OXIDATION; C-H THIOLATION; ORGANIC ELECTROSYNTHESIS; AROMATIC-COMPOUNDS; CYCLIZATION; AMINATION; FUNCTIONALIZATION; ACCESS; ARENES; DIFUNCTIONALIZATION;

D O I：

10.1016/j.chempr.2017.10.001

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxidative R-1-H/R-2-H cross-coupling represents an ideal way for the construction of new chemical bonds. However, the bond formation with loss of H-2 is typically thermodynamically unfavorable and thus usually requires an external driving force, namely, an appropriate sacrificial oxidant. Recent advances have revealed that oxidative R-1-H/R-2-H cross-coupling with hydrogen gas evolution can be achieved through electrochemical anodic oxidation and concomitant cathodic proton reduction. Electrochemistry provides new opportunities for the construction of carbon-carbon and carbon-heteroatom bonds in an environmentally friendly manner. This review article gives an overview of the recent developments in this emerging field.

引用

页码：27 / 45

页数：19

共 93 条

[1] Electrochemical recycling of benzoquinone in the Pd/benzoquinone-catalyzed Heck-type reactions from arenes [J].

Amatore, Christian ;

Cammoun, Chama ;

Jutand, Anny .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (03) :292-296

[2]

Anastas P., 1998, GREEN CHEM THEORY PR

[3] An anodic aromatic C,C cross-coupling reaction using parallel laminar flow mode in a flow microreactor [J].

Arai, Toshihiro ;

Tateno, Hiroyuki ;

Nakabayashi, Koji ;

Kashiwagi, Tsuneo ;

Atobe, Mahito .

CHEMICAL COMMUNICATIONS, 2015, 51 (23) :4891-4894

[4] Cooperative electrocatalytic alcohol oxidation with electron-proton-transfer mediators [J].

Badalyan, Artavazd ;

Stahl, Shannon S. .

NATURE, 2016, 535 (7612) :406-410

[5] Diversity-Oriented Synthesis of Polycyclic Scaffolds by Modification of an Anodic Product Derived from 2,4-Dimethylphenol [J].

Barjau, Joaquin ;

Schnakenburg, Gregor ;

Waldvogel, Siegfried R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (06) :1415-1419

[6] Electrocatalytic Aziridination of Alkenes Mediated by n-Bu4NI: A Radical Pathway [J].

Chen, Jie ;

Yan, Wei-Qing ;

Lam, Chiu Marco ;

Zeng, Cheng-Chu ;

Hu, Li-Ming ;

Little, R. Daniel .

ORGANIC LETTERS, 2015, 17 (04) :986-989

[7] Palladium-Catalyzed Aerobic Oxidative Cross-Coupling Reactions of Terminal Alkynes with Alkylzinc Reagents [J].

Chen, Mao ;

Zheng, Xiaolong ;

Li, Wenqing ;

He, Jun ;

Lei, Aiwen .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (12) :4101-+

[8] Dihydrobenzofuran synthesis by an anodic [3+2] cycloaddition of phenols and unactivated alkenes [J].

Chiba, K ;

Fukuda, M ;

Kim, S ;

Kitano, Y ;

Tada, M .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) :7654-7656

[9] Electrolytic Macrocyclizations: Scalable Synthesis of a Diazonamide-Based Drug Development Candidate [J].

Ding, Hui ;

DeRoy, Patrick L. ;

Perreault, Christian ;

Larivee, Alexandre ;

Siddiqui, Arshad ;

Caldwell, Charles G. ;

Harran, Susan ;

Harran, Patrick G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (16) :4818-4822

[10] DETECTION AND REACTIONS OF RADICAL CATIONS GENERATED BY PHOTOLYSIS OF AROMATIC-COMPOUNDS WITH TETRANITROMETHANE IN 1,1,1,3,3,3-HEXAFLUORO-2-PROPANOL AT ROOM-TEMPERATURE [J].

EBERSON, L ;

HARTSHORN, MP ;

PERSSON, O .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (20) :2268-2269

← 1 2 3 4 5 6 7 8 9 10 →