Specific Enhancement of Catalytic Activity by a Dicopper Core: Selective Hydroxylation of Benzene to Phenol with Hydrogen Peroxide

Tomokazu Tsuji, Antonius Andre Zaoputra, Yutaka Hitomi, Kaoru Mieda, Takashi Ogura, Yoshihito Shiota, Kazunari Yoshizawa, Hiroyasu Sato, Masahito Kodera

研究成果: ジャーナルへの寄稿記事

21 引用 (Scopus)

抄録

A dicopper(II) complex, stabilized by the bis(tpa) ligand 1,2-bis[2-[bis(2-pyridylmethyl)aminomethyl]-6-pyridyl]ethane (6-hpa), [Cu2(μ-OH)(6-hpa)]3+, was synthesized and structurally characterized. This complex catalyzed selective hydroxylation of benzene to phenol using H2O2, thus attaining large turnover numbers (TONs) and high H2O2 efficiency. The TON after 40 hours for the phenol production exceeded 12000 in MeCN at 50 °C under N2, the highest value reported for benzene hydroxylation with H2O2 catalyzed by homogeneous complexes. At 22 % benzene conversion, phenol (95.2 %) and p-benzoquinone (4.8 %) were produced. The mechanism of H2O2 activation and benzene hydroxylation is proposed.

元の言語英語
ページ(範囲)7779-7782
ページ数4
ジャーナルAngewandte Chemie - International Edition
56
発行部数27
DOI
出版物ステータス出版済み - 1 1 2017

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Hydroxylation
Phenol
Benzene
Hydrogen peroxide
Hydrogen Peroxide
Phenols
Catalyst activity
Ethane
Chemical activation
Ligands

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

これを引用

Specific Enhancement of Catalytic Activity by a Dicopper Core : Selective Hydroxylation of Benzene to Phenol with Hydrogen Peroxide. / Tsuji, Tomokazu; Zaoputra, Antonius Andre; Hitomi, Yutaka; Mieda, Kaoru; Ogura, Takashi; Shiota, Yoshihito; Yoshizawa, Kazunari; Sato, Hiroyasu; Kodera, Masahito.

:: Angewandte Chemie - International Edition, 巻 56, 番号 27, 01.01.2017, p. 7779-7782.

研究成果: ジャーナルへの寄稿記事

Tsuji, Tomokazu ; Zaoputra, Antonius Andre ; Hitomi, Yutaka ; Mieda, Kaoru ; Ogura, Takashi ; Shiota, Yoshihito ; Yoshizawa, Kazunari ; Sato, Hiroyasu ; Kodera, Masahito. / Specific Enhancement of Catalytic Activity by a Dicopper Core : Selective Hydroxylation of Benzene to Phenol with Hydrogen Peroxide. :: Angewandte Chemie - International Edition. 2017 ; 巻 56, 番号 27. pp. 7779-7782.
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abstract = "A dicopper(II) complex, stabilized by the bis(tpa) ligand 1,2-bis[2-[bis(2-pyridylmethyl)aminomethyl]-6-pyridyl]ethane (6-hpa), [Cu2(μ-OH)(6-hpa)]3+, was synthesized and structurally characterized. This complex catalyzed selective hydroxylation of benzene to phenol using H2O2, thus attaining large turnover numbers (TONs) and high H2O2 efficiency. The TON after 40 hours for the phenol production exceeded 12000 in MeCN at 50 °C under N2, the highest value reported for benzene hydroxylation with H2O2 catalyzed by homogeneous complexes. At 22 {\%} benzene conversion, phenol (95.2 {\%}) and p-benzoquinone (4.8 {\%}) were produced. The mechanism of H2O2 activation and benzene hydroxylation is proposed.",
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T2 - Selective Hydroxylation of Benzene to Phenol with Hydrogen Peroxide

AU - Tsuji, Tomokazu

AU - Zaoputra, Antonius Andre

AU - Hitomi, Yutaka

AU - Mieda, Kaoru

AU - Ogura, Takashi

AU - Shiota, Yoshihito

AU - Yoshizawa, Kazunari

AU - Sato, Hiroyasu

AU - Kodera, Masahito

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N2 - A dicopper(II) complex, stabilized by the bis(tpa) ligand 1,2-bis[2-[bis(2-pyridylmethyl)aminomethyl]-6-pyridyl]ethane (6-hpa), [Cu2(μ-OH)(6-hpa)]3+, was synthesized and structurally characterized. This complex catalyzed selective hydroxylation of benzene to phenol using H2O2, thus attaining large turnover numbers (TONs) and high H2O2 efficiency. The TON after 40 hours for the phenol production exceeded 12000 in MeCN at 50 °C under N2, the highest value reported for benzene hydroxylation with H2O2 catalyzed by homogeneous complexes. At 22 % benzene conversion, phenol (95.2 %) and p-benzoquinone (4.8 %) were produced. The mechanism of H2O2 activation and benzene hydroxylation is proposed.

AB - A dicopper(II) complex, stabilized by the bis(tpa) ligand 1,2-bis[2-[bis(2-pyridylmethyl)aminomethyl]-6-pyridyl]ethane (6-hpa), [Cu2(μ-OH)(6-hpa)]3+, was synthesized and structurally characterized. This complex catalyzed selective hydroxylation of benzene to phenol using H2O2, thus attaining large turnover numbers (TONs) and high H2O2 efficiency. The TON after 40 hours for the phenol production exceeded 12000 in MeCN at 50 °C under N2, the highest value reported for benzene hydroxylation with H2O2 catalyzed by homogeneous complexes. At 22 % benzene conversion, phenol (95.2 %) and p-benzoquinone (4.8 %) were produced. The mechanism of H2O2 activation and benzene hydroxylation is proposed.

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