Metal-Free Oxidative C-C Coupling of Arylamines Using a Quinone-Based Organic Oxidant

被引：33

作者：

Maddala, Sudhakar ^{[1
]}

Mallick, Sudesh ^{[1
]}

Venkatakrishnan, Parthasarathy ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 17期

关键词：

PALLADIUM-CATALYZED AMINATION; HOLE-TRANSPORT MATERIALS; AMORPHOUS MOLECULAR MATERIALS; AGGREGATION-INDUCED EMISSION; CATION-RADICALS; ARYL CHLORIDES; PERMANGANATE OXIDATION; AROMATIC AMINATION; CRYSTAL-STRUCTURES; SCHOLL REACTION;

D O I：

10.1021/acs.joc.7b01377

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of arylamines are shown to undergo oxidative C-C bond formation using quinone-based chloranil/H+ reagent as the recyclable organic (metal free) oxidant system to afford benzidines/naphthidines. Arylamines (3 degrees/2 degrees) designed with various substituents were employed to understand the steric as well as electronic preferences of oxidative dimerization, and a mechanism involving amine radical cation has been proposed. The tetraphenylbenzidine derivative obtained via oxidative C-C coupling has been further converted to blue-emissive hole-transporting material via a simple chemical transformation. This study highlights the preparation of novel HTMs in a simple, economic, and efficient manner.

引用

页码：8958 / 8972

页数：15

共 102 条

[1] MOLECULAR DESIGN OF HOLE TRANSPORT MATERIALS FOR OBTAINING HIGH DURABILITY IN ORGANIC ELECTROLUMINESCENT DIODES [J].

ADACHI, C ;

NAGAI, K ;

TAMOTO, N .

APPLIED PHYSICS LETTERS, 1995, 66 (20) :2679-2681

[2] A review on triphenylamine (TPA) based organic hole transport materials (HTMs) for dye sensitized solar cells (DSSCs) and perovskite solar cells (PSCs): evolution and molecular engineering [J].

Agarwala, Pooja ;

Kabra, Dinesh .

JOURNAL OF MATERIALS CHEMISTRY A, 2017, 5 (04) :1348-1373

[3]

[Anonymous], 2015, Organic Light-Emitting Materials and Devices

[4] Synthesis of conjugated multi-ynamides by copper-catalyzed reactions [J].

Betou, Marie ;

Sallustrau, Antoine ;

Toupet, Loic ;

Trolez, Yann .

TETRAHEDRON LETTERS, 2015, 56 (31) :4627-4630

[5] Oxidative Dimerization of Triarylamines Promoted by WCI6, Including the Solid State Isolation and the Crystallographic Characterization of a Triphenylammonium Salt [J].

Bortoluzzi, Marco ;

Marchetti, Fabio ;

Pampaloni, Guido ;

Pinzino, Calogero ;

Zacchini, Stefano .

INORGANIC CHEMISTRY, 2016, 55 (02) :887-893

[6] PERMANGANATE OXIDATION OF N-ARYL-2-NAPHTHYLAMINES [J].

BRIDGER, RF ;

LAW, DA ;

BOWMAN, DF ;

MIDDLETO.BS ;

INGOLD, KU .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (12) :4329-&

[7] RADICAL COUPLING PRODUCTS FROM PERMANGANATE OXIDATION OF N-PHENYL-2-NAPHTHYLAMINE [J].

BRIDGER, RF .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) :1746-+

[8] Effects of solvent and base on the palladium-catalyzed amination: PdCl2(Ph3P)2/Ph3P-catalyzed selective arylation of primary anilines with aryl bromides [J].

Cai, Liangzhen ;

Qian, Xuanying ;

Song, Wenjing ;

Liu, Taoping ;

Tao, Xiaochun ;

Li, Wanfang ;

Xie, Xiaomin .

TETRAHEDRON, 2014, 70 (32) :4754-4759

[9] Hole-Transport Materials for Perovskite Solar Cells [J].

Calio, Laura ;

Kazim, Samrana ;

Graetzel, Michael ;

Ahmad, Shahzada .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (47) :14522-14545

[10] Stille Polycondensation for Synthesis of Functional Materials [J].

Carsten, Bridget ;

He, Feng ;

Son, Hae Jung ;

Xu, Tao ;

Yu, Luping .

CHEMICAL REVIEWS, 2011, 111 (03) :1493-1528

← 1 2 3 4 5 6 7 8 9 10 →