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

被引：32

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 50 条

[41] Palladium-Catalyzed Sequential C-H Activation/Amination with Diaziridinone: An Approach to Indoles
Li, Jing
Chen, Jinhua
Wang, Luying
Shi, Yian
ORGANIC LETTERS, 2021, 23 (09) : 3646 - 3651
[42] Palladium-catalyzed intramolecular C-H amination using aluminum nitrate as the oxidant
Jia, Kai
Xue, Yuan
Tu, Daoquan
Luo, Jun
Jiang, Chao
ORGANIC CHEMISTRY FRONTIERS, 2022, 10 (01) : 109 - 114
[43] Palladium on Carbon-Catalyzed Benzylic Methoxylation for Synthesis of Mixed Acetals and Orthoesters
Yasukawa, Naoki
Kanie, Takafumi
Kuwata, Marina
Monguchi, Yasunari
Sajiki, Hironao
Sawama, Yoshinari
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (46) : 10974 - 10977
[44] Rhodium-Catalyzed C-H Amination: A Case Study of Selectivity in C-H Functionalization Reactions
Mack, James B. C.
Bedell, T. Aaron
DeLuca, Ryan J.
Hone, Graham A. B.
Roizen, Jennifer L.
Cox, Charles T.
Sorensen, Erik J.
Du Bois, J.
JOURNAL OF CHEMICAL EDUCATION, 2018, 95 (12) : 2243 - 2248
[45] Amination of benzylic C-H bonds by arylazides catalyzed by CoII-porphyrin complexes:: A synthetic and mechanistic study
Ragaini, F
Penoni, A
Gallo, E
Tollari, S
Gotti, CL
Lapadula, M
Mangioni, E
Cenini, S
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (01) : 249 - 259
[46] Synthesis of Carbazoles by Copper-Catalyzed Intramolecular C-H/N-H Coupling
Takamatsu, Kazutaka
Hirano, Koji
Satoh, Tetsuya
Miura, Masahiro
ORGANIC LETTERS, 2014, 16 (11) : 2892 - 2895
[47] Benzazetidine synthesis via palladium-catalysed intramolecular C-H amination
He, Gang
Lu, Gang
Guo, Zhengwei
Liu, Peng
Chen, Gong
NATURE CHEMISTRY, 2016, 8 (12) : 1131 - 1136
[48] A new copper catalyzed C-H bond amination protocol with unactivated amines: Mechanistic insights
Gephart, Raymond
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
[49] Iron-Catalyzed Primary C-H Amination of Sulfamate Esters and Its Application in Synthesis of Azetidines
Zhang, Yan
Zhong, Dayou
Usman, Muhammad
Xue, Peng
Liu, Wen-Bo
CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (12) : 1651 - 1655
[50] A novel catalytic one-pot synthesis of carbazoles via consecutive amination and C-H activation
Bedford, RB
Cazin, CSJ
CHEMICAL COMMUNICATIONS, 2002, (20) : 2310 - 2311

← 1 2 3 4 5 →