Supported palladium hydroxide-catalyzed intramolecular double C-H bond functionalization for synthesis of carbazoles and dibenzofurans

被引：40

作者：

Ishida, Tamao ^{[1
]}

Tsunoda, Ryosuke ^{[1
]}

Zhang, Zhenzhong ^{[1
]}

Hamasaki, Akiyuki ^{[1
]}

Honma, Tetsuo ^{[2
]}

Ohashi, Hironori ^{[3
]}

Yokoyama, Takushi ^{[1
]}

Tokunaga, Makoto ^{[1
,4
]}

机构：

[1] Kyushu Univ, Grad Sch Sci, Dept Chem, Higashi Ku, Fukuoka 8128581, Japan

[2] SPring 8, Japan Synchrotron Radiat Res Inst JASRI, Sayo, Hyogo 6795198, Japan

[3] Kyushu Univ, Fac Arts & Sci, Nishi Ku, Fukuoka 8190395, Japan

[4] Kyushu Univ, IRCMS, Nishi Ku, Fukuoka 8190395, Japan

来源：

APPLIED CATALYSIS B-ENVIRONMENTAL | 2014年 / 150卷

关键词：

C-H functionalization; Carbazole; Dibenzofuran; Palladium hydroxide; Heterogeneous catalyst; XAFS MEASUREMENT SYSTEM; DIRECT ARYLATION; ROOM-TEMPERATURE; N-ARYLATION; ACTIVATION; COMBUSTION; AMINATION; ARENES; ANILIDES; SPRING-8;

D O I：

10.1016/j.apcatb.2013.12.051

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Metal oxide-supported palladium hydroxide (Pd(OH)(2)/MOx) catalysts enabled the oxidative intramolecular couplings of diarylamines to carbazoles and diarylethers to dibenzofurans via double aryl C-H bond functionalizations with molecular oxygen as the sole oxidant. While supported PdO, Pd, and palladium acetate catalysts showed poor catalytic activities, supported Pd(OH)(2) exhibited remarkably high catalytic activity. Among supported Pd(OH)(2) catalysts, Pd(OH)(2)/ZrO2 was found to be an efficient catalyst in terms of catalytic activities and selectivities for the synthesis of carbazoles and dibenzofurans. (C) 2014 Elsevier B.V. All rights reserved.

引用

页码：523 / 531

页数：9

共 50 条

[41] Synthesis of Phenolic Compounds via Palladium Catalyzed C-H Functionalization of Arenes
Saha, Debajyoti
Das, Prasenjit
Biswas, Promita
Guin, Joyram
CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (24) : 4534 - 4548
[42] Metal-Catalyzed C-H Bond Functionalization
Baudoin, Olivier
TETRAHEDRON, 2013, 69 (22) : 4370 - 4370
[43] Palladium(II) Catalyzed C-H Functionalization Cascades for the Diastereoselective Synthesis of Polyheterocycles
Watt, Michael S.
Booker-Milburn, Kevin I.
ORGANIC LETTERS, 2016, 18 (21) : 5716 - 5719
[44] Dibenzo[a,c]carbazoles from 2-(2-bromoaryl)-3-arylindoles via a palladium-catalyzed intramolecular C-H functionalization/C-C bond formation process
Cacchi, Sandro
Fabrizi, Giancarlo
Goggiamani, Antonella
Iazzetti, Antonia
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (46) : 9142 - 9147
[45] Gold nanoparticle catalyzed intramolecular C-S bond formation/C-H bond functionalization/cyclization cascades
Gogoi, Prasanta
Paul, Bappi
Hazarika, Sukanya
Barman, Pranjit
RSC ADVANCES, 2015, 5 (71) : 57433 - 57436
[46] C-H bond functionalization in organic synthesis
Sanford, Melanie S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
[47] Intramolecular benzylic C-H activation: palladium-catalyzed synthesis of hexahydromethanofluorenes
Catellani, M
Motti, E
Ghelli, S
CHEMICAL COMMUNICATIONS, 2000, (20) : 2003 - 2004
[48] Combined C-H functionalization/C-N bond formation route to carbazoles
Tsang, WCP
Zheng, N
Buchwald, SL
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (42) : 14560 - 14561
[49] Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy
Beck, Elizabeth M.
Hatley, Richard
Gaunt, Matthew J.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (16) : 3004 - 3007
[50] Palladium on Carbon-Catalyzed C-H Amination for Synthesis of Carbazoles and its Mechanistic Study
Monguchi, Yasunari
Okami, Hiroki
Ichikawa, Tomohiro
Nozaki, Kei
Maejima, Toshihide
Oumi, Yasunori
Sawama, Yoshinari
Sajiki, Hironao
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (19) : 3145 - 3151

← 1 2 3 4 5 →