Electrochemical dehydrogenative cyclization of 1,3-dicarbonyl compounds

被引：94

作者：

Wu, Zheng-Jian

Li, Shi-Rui

Long, Hao

Xu, Hai-Chao ^{[1
]}

机构：

[1] Xiamen Univ, Innovat Collaborat Ctr Chem Energy Mat, Key Lab Chem Biol Fujian Prov, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 36期

基金：

中国国家自然科学基金;

关键词：

C-H; METAL-FREE; MANGANESE(III) ACETATE; RADICAL REACTIONS; TETRACYCLIC CORE; OXINDOLES; CATALYSIS; REAGENT; FUNCTIONALIZATION; GENERATION;

D O I：

10.1039/c8cc02472c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The intramolecular C(sp(3))-H/C(sp(2))-H cross-coupling of 1,3-dicarbonyl compounds has been achieved through Cp2Fe-catalyzed electrochemical oxidation. The key to the success of these dehydrogenative cyclization reactions is the selective activation of the acidic -C-H bond of the 1,3-dicarbonyl moiety to generate a carbon-centered radical.

引用

页码：4601 / 4604

页数：4

共 53 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] RADICAL-BASED SYNTHESES OF 5-BENZOYL-1,2-DIHYDRO-3H-PYRROLO[1,2-A]PYRROLE-1-CARBOXYLIC ACID (KETOROLAC) [J].

ARTIS, DR ;

CHO, IS ;

MUCHOWSKI, JM .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (06) :1838-1842

[3] DDQ-mediated Direct Intramolecular-Dehydrogenative-Coupling (IDC): Expeditious Approach to the Tetracyclic Core of Ergot Alkaloids [J].

Bhunia, Subhajit ;

Ghosh, Santanu ;

Dey, Dhananjay ;

Bisai, Alakesh .

ORGANIC LETTERS, 2013, 15 (10) :2426-2429

[4] Total synthesis and absolute configuration determination of (+)-subincanadine F [J].

Chen, Pinhong ;

Cao, Lidong ;

Tian, Wenhai ;

Wang, Xinfeng ;

Li, Chaozhong .

CHEMICAL COMMUNICATIONS, 2010, 46 (44) :8436-8438

[5] Low-Temperature, Transition-Metal-Free Cross-Dehydrogenative Coupling Protocol for the Synthesis of 3,3-Disubstituted Oxindoles [J].

Donald, James R. ;

Taylor, Richard J. K. ;

Petersen, Wade F. .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (20) :11288-11294

[6]

FernandezReina D., 2017, ACS CATAL, V7, P4126

[7] Redox catalysis in organic electrosynthesis: basic principles and recent developments [J].

Francke, Robert ;

Little, R. Daniel .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (08) :2492-2521

[8] Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones [J].

Fu, Niankai ;

Li, Longji ;

Yang, Qi ;

Luo, Sanzhong .

ORGANIC LETTERS, 2017, 19 (08) :2122-2125

[9] Intramolecular Dehydrogenative Coupling of sp2 C-H and sp3 C-H Bonds: An Expeditious Route to 2-Oxindoles [J].

Ghosh, Santanu ;

De, Subhadip ;

Kakde, Badrinath N. ;

Bhunia, Subhajit ;

Adhikary, Amit ;

Bisai, Alakesh .

ORGANIC LETTERS, 2012, 14 (23) :5864-5867

[10] The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling [J].

Hayashi, Ryutaro ;

Shimizu, Akihiro ;

Yoshida, Jun-ichi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (27) :8400-8403

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