Photoredox radical C-H oxygenation of aromatics with aroyloxylutidinium salts

被引：21

作者：

Miyazawa, Kazuki ^{[1
]}

Ochi, Rika ^{[1
]}

Koike, Takashi ^{[1
]}

Akita, Munetaka ^{[1
]}

机构：

[1] Tokyo Inst Technol, Inst Innovat Res, Lab Chem & Life Sci, Midori Ku, R1-27,4259 Nagatsuta Cho, Yokohama, Kanagawa, Japan

来源：

ORGANIC CHEMISTRY FRONTIERS | 2018年 / 5卷 / 09期

关键词：

CARBOXYLIC-ACIDS; PHTHALOYL PEROXIDE; CATALYSIS; HYDROXYLATION; AMINOHYDROXYLATION; FUNCTIONALIZATION; PHOTOCHEMISTRY; PHOTOPHYSICS; OLEFINS; MILD;

D O I：

10.1039/c8qo00089a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The photoredox-catalyzed aroyloxylation of aromatic C-H bonds with N-aroyloxylutidinium salts giving phenol derivatives has been developed. The present peroxide-free photocatalytic system is a convenient protocol for the generation of O-centered aroyloxy radicals under mild reaction conditions. In particular, N-3,5-bis(trifluoromethyl) phenylcarbonyloxylutidinium salt serves as an efficient aroyloxylating reagent by the action of Ir photocatalysts.

引用

收藏

页码：1406 / 1410

页数：5

相关论文

共 44 条

[1]

BARTON DHR, 1987, TETRAHEDRON, V43, P4321

[2] A scalable and operationally simple radical trifluoromethylation [J].

Beatty, Joel W. ;

Douglas, James J. ;

Cole, Kevin P. ;

Stephenson, Corey R. J. .

NATURE COMMUNICATIONS, 2015, 6

[3] Computational and Experimental Studies of Phthaloyl Peroxide-Mediated Hydroxylation of Arenes Yield a More Reactive Derivative, 4,5-Dichlorophthaloyl Peroxide [J].

Camelio, Andrew M. ;

Liang, Yong ;

Eliasen, Anders M. ;

Johnson, Trevor C. ;

Yuan, Changxia ;

Schuppe, Alex W. ;

Houk, K. N. ;

Siegel, Dionicio .

JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (16) :8084-8095

[4] Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals [J].

Candish, L. ;

Freitag, M. ;

Gensch, T. ;

Glorius, F. .

CHEMICAL SCIENCE, 2017, 8 (05) :3618-3622

[5] Photocatalytic Decarboxylative Reduction of Carboxylic Acids and Its Application in Asymmetric Synthesis [J].

Cassani, Carlo ;

Bergonzini, Giulia ;

Wallentin, Carl-Johan .

ORGANIC LETTERS, 2014, 16 (16) :4228-4231

[6] Visible light photoredox-controlled reactions of N-radicals and radical ions [J].

Chen, Jia-Rong ;

Hu, Xiao-Qiang ;

Lu, Liang-Qiu ;

Xiao, Wen-Jing .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) :2044-2056

[7] Redox-economical radical generation from organoborates and carboxylic acids by organic photoredox catalysis [J].

Chinzei, Tatsuya ;

Miyazawa, Kazuki ;

Yasu, Yusuke ;

Koike, Takashi ;

Akita, Munetaka .

RSC ADVANCES, 2015, 5 (27) :21297-21300

[8] A highly selective catalytic method for the oxidative functionalization of C-H bonds [J].

Dick, AR ;

Hull, KL ;

Sanford, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2300-2301

[9] Arene Oxidation with Malonoyl Peroxides [J].

Dragan, Andrei ;

Kubczyk, Tomasz M. ;

Rowley, Julian H. ;

Sproules, Stephen ;

Tomkinson, Nicholas C. O. .

ORGANIC LETTERS, 2015, 17 (11) :2618-2621

[10] A Protocol To Generate Phthaloyl Peroxide in Flow for the Hydroxylation of Arenes [J].

Eliasen, Anders M. ;

Thedford, Randal P. ;

Claussen, Karin R. ;

Yuan, Changxia ;

Siegel, Dionicio .

ORGANIC LETTERS, 2014, 16 (14) :3628-3631

← 1 2 3 4 5 →