A Visible-Light-Mediated Synthesis of Carbazoles

被引：175

作者：

Hernandez-Perez, Augusto C. ^{[1
,2
]}

Collins, Shawn K. ^{[1
,2
]}

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

[2] Univ Montreal, Ctr Green Chem & Catalysis, Montreal, PQ H3C 3J7, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 48期

基金：

加拿大自然科学与工程研究理事会;

关键词：

carbazoles; copper; heterocycles; photochemistry; PALLADIUM-CATALYZED SYNTHESIS; PHOTOREDOX CATALYSIS; PHOTOPHYSICAL PROPERTIES; PHOTOCHEMISTRY; DERIVATIVES; COMPLEXES; DEVICES; GREEN; PHOTOCYCLIZATION; DIPHENYLAMINES;

D O I：

10.1002/anie.201306920

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The photosynthetic preparation of N-aryl- and N-alkyl-bearing carbazoles utilizes continuous flow, visible light, and an in situ formed Cu-based sensitizer (see picture). The method is mild and efficient, and allows the straightforward synthesis of a variety of carbazoles with different substituents, heterocycles, and complex carbon architectures. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12696 / 12700

页数：5

共 81 条

[11]

CAUQUIS G, 1971, TETRAHEDRON LETT, P4645

[12] Microporous Polycarbazole with High Specific Surface Area for Gas Storage and Separation [J].

Chen, Qi ;

Luo, Min ;

Hammershoj, Peter ;

Zhou, Ding ;

Han, Ying ;

Laursen, Bo Wegge ;

Yan, Chao-Guo ;

Han, Bao-Hang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (14) :6084-6087

[13] 1,8-diamino-3,6-dichlorocarbazole: A promising building block for anion receptors [J].

Chmielewski, MJ ;

Charon, M ;

Jurczak, J .

ORGANIC LETTERS, 2004, 6 (20) :3501-3504

[14] Intramolecular Oxidative C-N Bond Formation for the Synthesis of Carbazoles: Comparison of Reactivity between the Copper-Catalyzed and Metal-Free Conditions [J].

Cho, Seung Hwan ;

Yoon, Jungho ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5996-6005

[15] PHOTOCYCLISATION OF ANILINO-PYRIDINES TO CARBOLINES [J].

CLARK, VM ;

COX, A ;

HERBERT, EJ .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (07) :831-&

[16] RUTHENIUM(II) TRIS(BIPYRAZYL) DICATION - A NEW PHOTOCATALYST [J].

CRUTCHLEY, RJ ;

LEVER, ABP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (23) :7128-7129

[17] Reductive quenching of photoexcited Cu(dipp)2+ and Cu(tptap)2+ by ferrocenes (dipp = 2,9-diisopropyl-1,10-phenanthroline and tptap = 2,3,6,7-tetraphenyl-1,4,5,8-tetraazaphenanthrene) [J].

Cunningham, KL ;

McMillin, DR .

INORGANIC CHEMISTRY, 1998, 37 (16) :4114-4119

[18]

CUPPEN JHM, 1972, J AM CHEM SOC, V94, P5914

[19] Simple Cu(I) complexes with unprecedented excited-state lifetimes [J].

Cuttell, DG ;

Kuang, SM ;

Fanwick, PE ;

McMillin, DR ;

Walton, RA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (01) :6-7

[20] Theoretical studies of symmetric five-membered heterocycle derivatives of carbazole and fluorene: Precursors of conducting polymers [J].

Doskocz, Jacek ;

Doskocz, Marek ;

Roszak, Szczepan ;

Soloducho, Jadwiga ;

Leszczynski, Jerzy .

JOURNAL OF PHYSICAL CHEMISTRY A, 2006, 110 (51) :13989-13994

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