Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate

被引：53

作者：

Chatterjee, Tanmay ^{[1
]}

Roh, Geum-bee ^{[1
]}

Shoaib, Mahbubul Alam ^{[2
]}

Suh, Chang-Heon ^{[3
]}

Kim, Jun Soo ^{[2
]}

Cho, Cheon-Gyu ^{[3
]}

Cho, Eun Jin ^{[1
]}

机构：

[1] Chung Ang Univ, Dept Chem, Seoul 06974, South Korea

[2] Ewha Womans Univ, Dept Chem Nanosci, Seoul 03760, South Korea

[3] Hanyang Univ, Dept Chem, Seoul 04763, South Korea

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 07期

基金：

新加坡国家研究基金会;

关键词：

MEDIATED SYNTHESIS; EMITTING-DIODES; HOST MATERIALS; PHOTOREDOX; DRIVEN; PHOTOCATALYSIS; IRRADIATION; ALKYLATION; ALDEHYDES; COMPLEX;

D O I：

10.1021/acs.orglett.7b00681

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A visible-light-induced synthesis of N-H carbazoles from easily accessible 2,2'-diaminobiaryls in the absence of any external photosensitizer is reported. The process only requires BuONO and natural resources, visible light, and molecular oxygen for the synthesis of N-H carbazoles. Experimental and computational studies support that the in situ formation of a visible-light-absorbing photosensitizing intermediate, benzocinnoline N-imide, is responsible for the activation of triplet molecular oxygen to singlet oxygen that, in turn, promotes the synthesis of carbazole.

引用

页码：1906 / 1909

页数：4

共 44 条

[1] Photochemical Perfluoroalkylation with Pyridine N-Oxides: Mechanistic Insights and Performance on a Kilogram Scale [J].

Beatty, Joel W. ;

Douglas, James J. ;

Miller, Richard ;

McAtee, Rory C. ;

Cole, Kevin P. ;

Stephenson, Corey R. J. .

CHEM, 2016, 1 (03) :456-472

[2] Carbazole compounds as host materials for triplet emitters in organic light-emitting diodes:: Tuning the HOMO level without influencing the triplet energy in small molecules [J].

Brunner, K ;

van Dijken, A ;

Börner, H ;

Bastiaansen, JJAM ;

Kiggen, NMM ;

Langeveld, BMW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) :6035-6042

[3] ARYNE CHEMISTRY .36. APPROACHES TO SYNTHESIS OF 5,6,7,8-TETRAHALOGENO-1,4-DIHYDRO-2-NITROSO-1,4-ETHENONAPHTHALENES (2-NITROSOTETRAHALOGENOBENZOBARRELENES) [J].

BUXTON, PC ;

HEANEY, H ;

MASON, KG ;

SKETCHLEY, JM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (23) :2695-2697

[4] Applications of Continuous-Flow Photochemistry in Organic Synthesis, Material Science, and Water Treatment [J].

Cambie, Dario ;

Bottecchia, Cecilia ;

Straathof, Natan J. W. ;

Hessel, Volker ;

Noel, Timothy .

CHEMICAL REVIEWS, 2016, 116 (17) :10276-10341

[5]

Chakraborty D. P., 1991, PROGR CHEM ORGANIC N, V57, P72

[6] Controlled Fluoroalkylation Reactions by Visible-Light Photoredox Catalysis [J].

Chatterjee, Tanmay ;

Iqbal, Naeem ;

You, Youngmin ;

Cho, Eun Jin .

ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) :2284-2294

[7] Visible-light-induced regioselective synthesis of polyheteroaromatic compounds [J].

Chatterjee, Tanmay ;

Choi, Myung Gil ;

Kim, Jun ;

Chang, Suk-Kyu ;

Cho, Eun Jin .

CHEMICAL COMMUNICATIONS, 2016, 52 (22) :4203-4206

[8] Synthesis of Carbazoles by a Merged Visible Light Photoredox and Palladium-Catalyzed Process [J].

Choi, Sungkyu ;

Chatterjee, Tanmay ;

Choi, Won Joon ;

You, Youngmin ;

Cho, Eun Jin .

ACS CATALYSIS, 2015, 5 (08) :4796-4802

[9] Visible-Light-Induced Arylthiofluoroalkylations of Unactivated Heteroaromatics and Alkenes [J].

Choi, Yeojin ;

Yu, Chunghyeon ;

Kim, Jun Soo ;

Cho, Eun Jin .

ORGANIC LETTERS, 2016, 18 (13) :3246-3249

[10] Visible-Light-Mediated Generation of Nitrogen-Centered Radicals: Metal-Free Hydroimination and Iminohydroxylation Cyclization Reactions [J].

Davies, Jacob ;

Booth, Samuel G. ;

Essafi, Stephanie ;

Dryfe, Robert A. W. ;

Leonori, Daniele .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (47) :14017-14021

← 1 2 3 4 5 →