Selective activation of C-H bond into C=0 bond of phenols in para-position via aerobic oxidation

被引：9

作者：

Yang, Shilei ^{[1
]}

Xu, Guoqiang ^{[1
]}

Shi, Song ^{[2
]}

Xin, Hongchuan ^{[1
]}

Gao, Jin ^{[2
]}

An, Zengjian ^{[1
]}

机构：

[1] Chinese Acad Sci, Qingdao Inst Bioenergy & Bioproc Technol, Key Lab Biobased Mat, Qingdao 266101, Peoples R China

[2] Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian Natl Lab Clean Energy, Dalian 116023, Peoples R China

来源：

CATALYSIS COMMUNICATIONS | 2019年 / 123卷

关键词：

Selective activation; C-H bond; C=O bond; Phenols; Aerobic oxidation; AQUEOUS HYDROGEN-PEROXIDE; COPPER(II) CHLORIDE; H2O2-BASED OXIDATION; CATALYZED OXIDATION; 2,3,6-TRIMETHYLPHENOL; 2,3,5-TRIMETHYLBENZOQUINONE; TRIMETHYL-1,4-BENZOQUINONE; 2,3,5-TRIMETHYLPHENOL; BENZOQUINONES; ALKYLPHENOLS;

D O I：

10.1016/j.catcom.2019.02.017

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：

An efficient method for the oxidation of phenols to 1,4-benzoquinones catalyzed by cuprous(I) chloride was achieved in a solution of acetonitrile and water using molecular dioxygen as an oxidant. Particularly, the inert phenols, such as phenol and mono-alkyl substituted phenols, were effectively oxidized to 1,4-benzoquinones via the selective activation of C-H bond in para-position into C=O bond under mild conditions. The catalyst shows high activity for unsubstituted or alkyl substituted phenols, but no effect on substituted phenols with electron withdrawing groups. This study offers an aerobic method for the selective oxidation of aromatic phenols to 1,4-benzoquinones.

引用

页码：105 / 108

页数：4

共 50 条

[41] Pd/Norbornene: A Winning Combination for Selective Aromatic Functionalization via C-H Bond Activation
Della Ca, Nicola
Fontana, Marco
Motti, Elena
Catellani, Marta
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (07) : 1389 - 1400
[42] SELECTIVE ARYLATION OF A SI-H BOND IN O-BIS(DIMETHYLSILYL)BENZENE VIA C-H BOND ACTIVATION OF ARENES
UCHIMAU, Y
MOUNEER, A
ELSAYED, M
TANAKA, M
ORGANOMETALLICS, 1993, 12 (06) : 2065 - 2069
[43] Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation
Colby, Denise A.
Bergman, Robert G.
Ellman, Jonathan A.
CHEMICAL REVIEWS, 2010, 110 (02) : 624 - 655
[44] C-C bond formation via C-H bond activation: Synthesis of the core of teleocidin B4
Dangel, BD
Godula, K
Youn, SW
Sezen, B
Sames, D
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (40) : 11856 - 11857
[45] Oxidative ortho-amino-methylation of phenols via C-H and C-C bond cleavage
Sun, Wenbo
Lin, Huacan
Zhou, Wenyu
Li, Zigang
RSC ADVANCES, 2014, 4 (15) : 7491 - 7494
[46] C-P bond formation via selective electrocatalytic C-H phosphorylation
Khrizanforov, M. N.
Strekalova, S. O.
Grinenko, V. V.
Kononov, A. I.
Dolengovski, E. L.
Budnikova, Y. H.
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2019, 194 (4-6) : 384 - 385
[47] C-C Bond Formation via C-H Bond Activation Using an in Situ-Generated Ruthenium Catalyst
Martinez, Remi
Simon, Marc-Olivier
Chevalier, Reynald
Pautigny, Cyrielle
Genet, Jean-Pierre
Darses, Sylvain
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) : 7887 - 7895
[48] SYNTHESIS OF IRIDAOXACYCLOHEXADIENE AND IRIDACYCLOPENTENONE COMPLEXES VIA C-H BOND ACTIVATION
BLEEKE, JR
HAILE, T
CHIANG, MY
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 201 : 116 - INOR
[49] Iridium-Catalyzed Hydroarylation via C-H Bond Activation
Nishimura, Takahiro
CHEMICAL RECORD, 2021, 21 (12): : 3532 - 3545
[50] Annulation of aromatic Imines via directed C-H bond activation
Thalji, RK
Ahrendt, KA
Bergman, RG
Ellman, JA
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (17): : 6775 - 6781

← 1 2 3 4 5 →