Transition-Metal-Free Oxyarylation of Alkenes with Aryl Diazonium Salts and TEMPONa

被引：168

作者：

Hartmann, Marcel ^{[1
]}

Li, Yi ^{[1
]}

Studer, Armido ^{[1
]}

机构：

[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 40期

关键词：

PALLADIUM-CATALYZED REACTIONS; POLAR CROSSOVER REACTIONS; C-H FUNCTIONALIZATION; REDUCTIVE CARBODIAZENYLATION; OXIDATIVE OXYARYLATION; COUPLING REACTIONS; ARYLBORONIC ACIDS; FUSED-RING; CARBOETHERIFICATION; RADICALS;

D O I：

10.1021/ja307638u

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of readily available TEMPO-Na with aryl diazonium salts allows for clean generation of the corresponding aryl radicals along with TEMPO. Aryl radical addition to alkenes with subsequent TEMPO trapping provides the corresponding oxyarylation products in good to excellent yields. These experimentally easy to conduct transformations occur in the absence of any transition metal under mild conditions, and the process shows broad functional group compatibility.

引用

页码：16516 / 16519

页数：4

共 74 条

[1]

Baguley PA, 1998, ANGEW CHEM INT EDIT, V37, P3073, DOI 10.1002/(SICI)1521-3773(19981204)37:22<3072::AID-ANIE3072>3.0.CO

[2]

2-9

[3] Gold-Catalysed Oxyarylation of Styrenes and Mono- and gem-Disubstituted Olefins Facilitated by an Iodine(III) Oxidant [J].

Ball, Liam T. ;

Lloyd-Jones, Guy C. ;

Russell, Christopher A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (10) :2931-2937

[4] Arylsilanes: Application to Gold-Catalyzed Oxyarylation of Alkenes [J].

Ball, Liam T. ;

Green, Michael ;

Lloyd-Jones, Guy C. ;

Russell, Christopher A. .

ORGANIC LETTERS, 2010, 12 (21) :4724-4727

[5] The role of neighbouring group participation in TTF-mediated 'radical-polar crossover' reactions:: trapping of aliphatic radicals by TTF+• [J].

Bashir, N ;

Murphy, JA .

CHEMICAL COMMUNICATIONS, 2000, (07) :627-628

[6] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[7] Gold-Catalyzed Oxidative Coupling Reactions with Aryltrimethylsilanes [J].

Brenzovich, William E., Jr. ;

Brazeau, Jean-Francois ;

Toste, F. Dean .

ORGANIC LETTERS, 2010, 12 (21) :4728-4731

[8]

Chatgilialoglu C., 2012, Encyclopedia of Radicals in Chemistry Biology and Materials, V1

[9]

Chatgilialoglu C., 2012, ENCY RADICALS CHEM B, V2

[10] Recent Advances in Ligand Design for the Intermolecular Asymmetric Mizoroki-Heck Reaction [J].

Coeffard, Vincent ;

Guiry, Patrick J. .

CURRENT ORGANIC CHEMISTRY, 2010, 14 (03) :212-229

← 1 2 3 4 5 6 7 8 →