Palladium on Carbon-Catalyzed C-H Amination for Synthesis of Carbazoles and its Mechanistic Study

被引：33

作者：

Monguchi, Yasunari ^{[1
]}

Okami, Hiroki ^{[1
]}

Ichikawa, Tomohiro ^{[1
]}

Nozaki, Kei ^{[1
]}

Maejima, Toshihide ^{[1
]}

Oumi, Yasunori ^{[2
]}

Sawama, Yoshinari ^{[1
]}

Sajiki, Hironao ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Organ Chem Lab, 1-25-4 Daigaku Nishi, Gifu 5011196, Japan

[2] Gifu Univ, Life Sci Res Ctr, Instrumental Anal, 1-1 Yanagido, Gifu 5011193, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 19期

关键词：

C-H amination; heterogeneous catalysis; nitrogen heterocycles; nitrogen oxides; palladium; MIYAURA COUPLING REACTION; BENZYL PROTECTIVE GROUP; LIGAND-FREE; HETEROGENEOUS PD/C; DIRECT ARYLATION; BOND FORMATION; FUNCTIONALIZATION; HYDROGENOLYSIS; INHIBITION; ROUTE;

D O I：

10.1002/adsc.201600299

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

10% Palladium on carbon (10% Pd/C) successfully catalyzed the intramolecular C-H amination of various N-mesylated 2-aminobiphenyls in the presence of a catalytic amount of pyridine N-oxide in heated dimethyl sulfoxide (DMSO) under an oxygen atmosphere to afford the corresponding N-mesylcarbazoles. The reaction would proceed via a single-electron transfer process based on its significant suppression by the addition of a single-electron scavenger, tetracyanoquinodimethane (TCNQ), and the substituents on the aromatic rings of the substrate have an insignificant effect on the reaction progress.

引用

页码：3145 / 3151

页数：7

共 69 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].