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

Tamao Ishida; Ryosuke Tsunoda; Zhenzhong Zhang; Akiyuki Hamasaki; Tetsuo Honma; Hironori Ohashi; Takushi Yokoyama; Makoto Tokunaga

doi:10.1016/j.apcatb.2013.12.051

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

Tamao Ishida, Ryosuke Tsunoda, Zhenzhong Zhang, Akiyuki Hamasaki, Tetsuo Honma, Hironori Ohashi, Takushi Yokoyama, Makoto Tokunaga

Research output: Contribution to journal › Article › peer-review

37 Citations (Scopus)

Abstract

Metal oxide-supported palladium hydroxide (Pd(OH)₂/MO_x) catalysts enabled the oxidative intramolecular couplings of diarylamines to carbazoles and diarylethers to dibenzofurans via double aryl CH 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.

Original language	English
Pages (from-to)	523-531
Number of pages	9
Journal	Applied Catalysis B: Environmental
Volume	150-151
DOIs	https://doi.org/10.1016/j.apcatb.2013.12.051
Publication status	Published - May 5 2014

All Science Journal Classification (ASJC) codes

Catalysis
Environmental Science(all)
Process Chemistry and Technology

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10.1016/j.apcatb.2013.12.051

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title = "Supported palladium hydroxide-catalyzed intramolecular double CH bond functionalization for synthesis of carbazoles and dibenzofurans",

abstract = "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 CH 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.",

author = "Tamao Ishida and Ryosuke Tsunoda and Zhenzhong Zhang and Akiyuki Hamasaki and Tetsuo Honma and Hironori Ohashi and Takushi Yokoyama and Makoto Tokunaga",

note = "Funding Information: This work was financially supported by JST-ALCA (FS Stage). The synchrotron radiation experiments were performed at the BL14B2 in SPring-8 with the approval of JASRI (2011B1001, 2012A1454, and 2012B1075). ",

year = "2014",

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doi = "10.1016/j.apcatb.2013.12.051",

language = "English",

volume = "150-151",

pages = "523--531",

journal = "Applied Catalysis B: Environmental",

issn = "0926-3373",

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TY - JOUR

T1 - Supported palladium hydroxide-catalyzed intramolecular double CH bond functionalization for synthesis of carbazoles and dibenzofurans

AU - Ishida, Tamao

AU - Tsunoda, Ryosuke

AU - Zhang, Zhenzhong

AU - Hamasaki, Akiyuki

AU - Honma, Tetsuo

AU - Ohashi, Hironori

AU - Yokoyama, Takushi

AU - Tokunaga, Makoto

N1 - Funding Information: This work was financially supported by JST-ALCA (FS Stage). The synchrotron radiation experiments were performed at the BL14B2 in SPring-8 with the approval of JASRI (2011B1001, 2012A1454, and 2012B1075).

PY - 2014/5/5

Y1 - 2014/5/5

N2 - 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 CH 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.

AB - 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 CH 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.

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DO - 10.1016/j.apcatb.2013.12.051

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SN - 0926-3373

VL - 150-151

SP - 523

EP - 531

JO - Applied Catalysis B: Environmental

JF - Applied Catalysis B: Environmental

ER -

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

Abstract

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