Catalytic C-H oxidation by a triazamacrocyclic ruthenium complex

被引：67

作者：

McNeill, Eric ^{[1
]}

Du Bois, J. ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

CHEMICAL SCIENCE | 2012年 / 3卷 / 06期

基金：

美国国家科学基金会;

关键词：

SATURATED-HYDROCARBONS; RUO4-MEDIATED OXIDATIONS; CIS-DIOXORUTHENIUM(VI) COMPLEX; HYDROXYLATION; MECHANISM; FUNCTIONALIZATION; SELECTIVITY; EPOXIDATION; REACTIVITY; ALKENES;

D O I：

10.1039/c2sc20118f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A method for oxygenation of tertiary and benzylic C-H bonds is described that uses 1-10 mol% (1,4,7-trimethyl-1,4,7-triazacyclo-nonane) ruthenium(III) trichloride as catalyst and ceric (IV) ammonium nitrate (CAN) as the terminal oxidant. The reaction is conveniently performed in aqueous solvent mixtures on substrates bearing a number of common, polar functional groups. The scope and efficiency of this process are comparable or superior to other known catalytic C-H oxidation technologies. Chemoselectivity trends and kinetic isotope effect data implicate a stepwise, radical-rebound mechanism for this transformation.

引用

收藏

页码：1810 / 1813

页数：4

相关论文

共 50 条

[41] Ruthenium Metal: Uplifting Regioselective C-H Activation [J].

Pal, Munish ;

Purohit, Priyank ;

Upadhyay, Prabhat .

LETTERS IN ORGANIC CHEMISTRY, 2022, 19 (07) :520-531

[42] Ruthenium-catalyzed C-H activation of thioxanthones [J].

Wagner, Danny ;

Braese, Stefan .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 :431-435

[43] C-H Monoarylation of Naphthylpyrimidines with Aryl Chlorides Catalyzed by a Water-Soluble Ruthenium Complex [J].

Li, Hong-Mei ;

Tu, Tian-Yong ;

Han, Xin ;

Wang, Zhi-Qiang ;

Fu, Wei-Jun ;

Hao, Xin-Qi ;

Song, Mao-Ping ;

Xu, Chen .

SYNLETT, 2018, 29 (13) :1729-1734

[44] Catalytic C-H bond arylation of aryl imines and oxazolines in water with ruthenium(II)-acetate catalyst [J].

Li, Bin ;

Devaraj, Karthik ;

Darcel, Christophe ;

Dixneuf, Pierre H. .

TETRAHEDRON, 2012, 68 (26) :5179-5184

[45] Ruthenium-Mediated Dual Catalytic Reactions of Isoquinoline via C-H Activation and Dearomatization for Isoquinolone [J].

Wang, Ting-Hsuan ;

Lee, Wei-Chih ;

Ong, Tiow-Gan .

ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (17) :2751-2758

[46] Highly regioselective oxidation of C-H bonds in water using hydrogen peroxide by a cytochrome P450 mimicking iron complex [J].

Jana, Sandipan ;

De, Puja ;

Dey, Chinmay ;

Dey, Somdatta Ghosh ;

Dey, Abhishek ;

Sen Gupta, Sayam .

CHEMICAL SCIENCE, 2023, 14 (38) :10515-10523

[47] Mechanistic Guidance Leads to Enhanced Site-Selectivity in C-H Oxidation Reactions Catalyzed by Ruthenium bis(Bipyridine) Complexes [J].

Griffin, Jeremy D. ;

Vogt, David B. ;

Du Bois, J. ;

Sigman, Matthew S. .

ACS CATALYSIS, 2021, 11 (16) :10479-10486

[48] Ruthenium-Catalyzed Carbonylation of ortho C-H Bonds in Arylacetamides: C-H Bond Activation Utilizing a Bidentate-Chelation System [J].

Shibata, Kaname ;

Hasegawa, Nao ;

Fukumoto, Yoshiya ;

Chatani, Naoto .

CHEMCATCHEM, 2012, 4 (11) :1733-1736

[49] Ruthenium-Catalyzed Oxidative C-H Alkenylations of Anilides and Benzamides in Water [J].

Ackermann, Lutz ;

Wang, Lianhui ;

Wolfram, Ratnakancana ;

Lygin, Alexander V. .

ORGANIC LETTERS, 2012, 14 (03) :728-731

[50] Catalytic C-H Trifluoromethoxylation of Arenes and Heteroarenes [J].

Zheng, Weijia ;

Morales-Rivera, Cristian A. ;

Lee, Johnny W. ;

Liu, Peng ;

Ngai, Ming-Yu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (31) :9645-9649

← 1 2 3 4 5 →