Visible-light-mediated oxidative arylation of vinylarenes under aerobic conditions

被引：43

作者：

Bu, Meijie ^{[1
]}

Niu, Teng Fei ^{[1
]}

Cai, Chun ^{[1
]}

机构：

[1] Nanjing Univ Sci & Technol, Chem Engn Coll, Nanjing 210094, Jiangsu, Peoples R China

来源：

CATALYSIS SCIENCE & TECHNOLOGY | 2015年 / 5卷 / 02期

关键词：

CATALYZED ALPHA-ARYLATION; PHOTOREDOX CATALYSIS; KETONES; DIHYDROXYLATION; OXYALKYLATION; CONSTRUCTION; ALKYLATION; ALDEHYDES; CLEAVAGE; STYRENES;

D O I：

10.1039/c4cy01523a

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A mild and efficient method for the photocatalytic oxidative arylation of vinylarenes to generate 1,2-diarylated ethanones has been developed. The reaction was catalyzed by Ru(bpy)(3)Cl-2 at room temperature under aerobic conditions. This protocol realizes a controllable, regioselective 1,2-difunctionalization of carbon-carbon double bonds.

引用

页码：830 / 834

页数：5

共 52 条

[1] CuBr-Mediated Oxyalkylation of Vinylarenes under Aerobic Conditions via Cleavage of sp3 C-H Bonds α to Oxygen [J].

Cheng, Kai ;

Huang, Lehao ;

Zhang, Yuhong .

ORGANIC LETTERS, 2009, 11 (13) :2908-2911

[2] Oxidation of the Benzyl Radical: Mechanism, Thermochemistry, and Kinetics for the Reactions of Benzyl Hydroperoxide [J].

da Silva, Gabriel ;

Hamdan, M. Rafiq ;

Bozzelli, Joseph W. .

JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2009, 5 (12) :3185-3194

[3] Construction of tetrahydrofurans by PdII/PdIV-catalyzed aminooxygenation of alkenes [J].

Desai, Lopa V. ;

Sanford, Melanie S. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (30) :5737-5740

[4] Highly active and selective catalysts for the formation of α-aryl ketones [J].

Fox, JM ;

Huang, XH ;

Chieffi, A ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (07) :1360-1370

[5] Oxyarylation and Aminoarylation of Styrenes Using Photoredox Catalysis [J].

Fumagalli, Gabriela ;

Boyd, Scott ;

Greaney, Michael F. .

ORGANIC LETTERS, 2013, 15 (17) :4398-4401

[6]

Griesbeck AG, 1996, LIEBIGS ANN-RECL, P545

[7] Palladium-catalyzed direct α-arylation of ketones.: Rate acceleration by sterically hindered chelating ligands and reductive elimination from a transition metal enolate complex [J].

Hamann, BC ;

Hartwig, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12382-12383

[8] Synthetic applications of eosin Y in photoredox catalysis [J].

Hari, Durga Prasad ;

Koenig, Burkhard .

CHEMICAL COMMUNICATIONS, 2014, 50 (51) :6688-6699

[9] The Photoredox-Catalyzed Meerwein Addition Reaction: Intermolecular Amino-Arylation of Alkenes [J].

Hari, Durga Prasad ;

Hering, Thea ;

Koenig, Burkhard .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (03) :725-728

[10] Metal-Free, Visible-Light-Mediated Direct C-H Arylation of Heteroarenes with Aryl Diazonium Salts [J].

Hari, Durga Prasad ;

Schroll, Peter ;

Koenig, Burkhard .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (06) :2958-2961

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