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

[31] Palladium(II)-Catalyzed Intramolecular C-H Alkenylation for the Synthesis of Chromanes [J].

Carral-Menoyo, Asier ;

Misol, Alexander ;

Gomez-Redondo, Marcos ;

Sotomayor, Nuria ;

Lete, Esther .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04) :2048-2060

[32] Palladium-Catalyzed intramolecular C-H Activation/C-C Bond Formation: A Straightforward Synthesis of Phenanthridines [J].

Peng, Jinsong ;

Chen, Tonghui ;

Chen, Chunxia ;

Li, Bin .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22) :9507-9513

[33] Amine directed Pd(II)-catalyzed C-H bond functionalization under ambient conditions [J].

Haffemayer, Benjamin ;

Gulias, Moises ;

Gaunt, Matthew J. .

CHEMICAL SCIENCE, 2011, 2 (02) :312-315

[34] Pd-Catalyzed C-H Bond Functionalization on the Indole and Pyrrole Nucleus [J].

Beck, Elizabeth M. ;

Gaunt, Matthew J. .

C-H ACTIVATION, 2010, 292 :85-121

[35] Palladium-catalyzed alkenation of thiophenes and furans by regioselective C-H bond functionalization [J].

Zhao, Jinlong ;

Huang, Lehao ;

Cheng, Kai ;

Zhang, Yuhong .

TETRAHEDRON LETTERS, 2009, 50 (23) :2758-2761

[36] Functionalization of [60]Fullerene via Palladium-Catalyzed C-H Bond Activation [J].

Wang, Guan-Wu .

C-H BOND ACTIVATION AND CATALYTIC FUNCTIONALIZATION I, 2016, 55 :119-136

[37] Isocanthine Synthesis via Rh(III)-Catalyzed Intramolecular C-H Functionalization [J].

Chen, Anthony Y. ;

Lu, Qianqian ;

Fu, Yao ;

Sarpong, Richmond ;

Stoltz, Brian M. ;

Zhang, Haiming .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01) :330-337

[38] Synthesis of Oxindoles by Palladium-catalyzed C-H Bond Amidation [J].

Miura, Tomoya ;

Ito, Yoshiteru ;

Murakami, Masahiro .

CHEMISTRY LETTERS, 2009, 38 (04) :328-329

[39] Iron-catalyzed intramolecular C-H amination for the synthesis of N-H carbazoles and indoles [J].

Wang, Zheng-Lin ;

Zhang, Yun-Hao ;

Huang, Jun-Yu ;

Zhou, Jian ;

Yu, Ya-Qin ;

Feng, Dexin ;

Xu, Da-Zhen .

GREEN CHEMISTRY, 2023, 25 (11) :4463-4468

[40] Progress in the Synthesis of Primary Anilines via C-H Bond Functionalization [J].

Xu, Linlin ;

Xu, Hui ;

Lin, Haixia ;

Dai, Huixiong .

CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (08) :1940-1948

← 1 2 3 4 5 →