Catalyst-controlled site-selective N-H and C3-arylation of carbazole via carbene transfer reactions

被引:22
作者
Bera, Sourav Sekhar [1 ]
Bahukhandi, Srishti Ballabh [1 ]
Empel, Claire [1 ]
Koenigs, Rene M. [1 ]
机构
[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany
关键词
BOND FUNCTIONALIZATION; BLUE ELECTROLUMINESCENCE; DIAZO REAGENTS; GOLD; DERIVATIVES; INSERTION; LIGAND;
D O I
10.1039/d1cc01863a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A site-selective direct arylation reaction of carbazole and other N-heterocycles with diazo-naphthalen-2(1H)-ones has been developed. While Au(i)-NHC catalysts lead to selective C3-arylation, palladium acetate allows for selective N-H arylation, displaying complete site-selectivity each. To show the applicability of these arylation reactions, one-pot, two-fold diarylation reactions of carbazole were demonstrated.
引用
收藏
页码:6193 / 6196
页数:4
相关论文
共 56 条
[1]   Recent advances in the synthesis of carbazoles from indoles [J].
Aggarwal, Trapti ;
Sushmita ;
Verma, Akhilesh K. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (36) :8330-8342
[2]   Enantioselective Palladium-Catalyzed Carbene Insertion into the N-H Bonds of Aromatic Heterocycles [J].
Arredondo, Vanessa ;
Hiew, Stanley C. ;
Gutman, Eugene S. ;
Premachandra, Ilandari Dewage Udara Anulal ;
Van Vranken, David L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (15) :4156-4159
[3]   Studies on the Enantioselective Iminium Ion Trapping of Radicals Triggered by an Electron-Relay Mechanism [J].
Bahamonde, Ana ;
Murphy, John J. ;
Savarese, Marika ;
Bremond, Eric ;
Cavalli, Andrea ;
Melchiorre, Paolo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (12) :4559-4567
[4]   Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products [J].
Bringmann, Gerhard ;
Gulder, Tanja ;
Gulder, Tobias A. M. ;
Breuning, Matthias .
CHEMICAL REVIEWS, 2011, 111 (02) :563-639
[5]   Sequential Au(I)/chiral tertiary amine catalysis: a tandem C-H functionalization of anisoles or a thiophene/asymmetric Michael addition sequence to quaternary oxindoles [J].
Cao, Zhong-Yan ;
Zhao, Yu-Lei ;
Zhou, Jian .
CHEMICAL COMMUNICATIONS, 2016, 52 (12) :2537-2540
[6]   Aggregation-induced emission, mechanochromism and blue electroluminescence of carbazole and triphenylamine-substituted ethenes [J].
Chan, Carrie Y. K. ;
Lam, Jacky W. Y. ;
Zhao, Zujin ;
Chen, Shuming ;
Lu, Ping ;
Sung, Herman H. Y. ;
Kwok, Hoi Sing ;
Ma, Yuguang ;
Williams, Ian D. ;
Tang, Ben Zhong .
JOURNAL OF MATERIALS CHEMISTRY C, 2014, 2 (21) :4320-4327
[7]   Rh-Catalyzed Intermolecular Carbenoid Functionalization of Aromatic C-H Bonds by α-Diazomalonates [J].
Chan, Wai-Wing ;
Lo, Siu-Fung ;
Zhou, Zhongyuan ;
Yu, Wing-Yiu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (33) :13565-13568
[8]   Photocatalytic Alkylation of Pyrroles and Indoles with α-Diazo Esters [J].
Ciszewski, Lukasz W. ;
Durka, Jakub ;
Gryko, Dorota .
ORGANIC LETTERS, 2019, 21 (17) :7028-7032
[9]   Photoinduced Ullmann C-N Coupling: Demonstrating the Viability of a Radical Pathway [J].
Creutz, Sidney E. ;
Lotito, Kenneth J. ;
Fu, Gregory C. ;
Peters, Jonas C. .
SCIENCE, 2012, 338 (6107) :647-651
[10]   Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion [J].
Davies, Huw M. L. ;
Manning, James R. .
NATURE, 2008, 451 (7177) :417-424