TY - JOUR
T1 - Specific Enhancement of Catalytic Activity by a Dicopper Core
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
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research (B) JSPS KAKENHI Grant Number 26288027, and CREST, JST.
Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
PY - 2017/6/26
Y1 - 2017/6/26
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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U2 - 10.1002/anie.201702291
DO - 10.1002/anie.201702291
M3 - Article
C2 - 28561921
AN - SCOPUS:85020000852
SN - 1433-7851
VL - 56
SP - 7779
EP - 7782
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 27
ER -