Heterogeneous Esterification from α-Hydroxy Ketone and Alcohols through a Tandem Oxidation Process over a Hydrotalcite-Supported Bimetallic Catalyst

被引：13

作者：

Meng, Xu ^{[1
]}

Bi, Xiuru ^{[1
]}

Chen, Gexin ^{[1
]}

Chen, Baohua ^{[2
]}

Zhao, Peiqing ^{[1
]}

机构：

[1] Chinese Acad Sci, State Key Lab Oxo Synth & Select Oxidat, Suzhou Res Inst LICP, LICP, Lanzhou 730000, Gansu, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2018年 / 22卷 / 12期

基金：

中国国家自然科学基金;

关键词：

oxidative esterification; alpha-keto esters; hydrotalcite; heterogeneous synthesis; supported catalyst; LAYERED DOUBLE HYDROXIDE; AEROBIC OXIDATION; MOLECULAR-OXYGEN; P-CRESOL; MANGANESE; KETOESTERS; EFFICIENT; COPPER; ACETOPHENONES; ESTERS;

D O I：

10.1021/acs.oprd.8b00265

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Heterogeneous aerobic oxidative esterification between a-hydroxy ketone and alcohols catalyzed by a hydrotalcite-supported bimetallic catalyst (CuMn/HT) using O-2 as a green oxidant was achieved. Recyclable CuMn/HT exhibits high catalytic activity due to increased content of oxygen vacancies and a newly generated CuMn2O4 crystal phase. This clean esterification proceeds through a tandem oxidation process in the absence of any additives and ligands and affords alpha-keto esters in good to excellent yields. Moreover, the catalytic system tolerates complicated bioactive molecules as raw materials and can be performed on a multigram scale.

引用

页码：1716 / 1722

页数：7

共 53 条

[11] Metal-free oxidative esterification of acetophenones with alcohols: a facile one-pot approach to α-ketoesters
Guo, Shiyu
Dai, Zhongxue
Yang, Zhao
Zhu, Ning
Wan, Li
Li, Xin
Liu, Chengkou
Fang, Zheng
Guo, Kai
[J]. RSC ADVANCES, 2016, 6 (100): : 98422 - 98426
[12] α-ketoamides, α-ketoesters and α-diketones as HCVNS3 protease inhibitors
Han, W
Hu, ZL
Jiang, XJ
Decicco, CP
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (08) : 711 - 713
[13] Catalytic Enantioselective Protonation of α-Oxygenated Ester Enolates Prepared through Phospha-Brook Rearrangement
Hayashi, Masashi
Nakamura, Shuichi
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (10) : 2249 - 2252
[14] Tremendous effect of oxygen vacancy defects on the oxidation of arsenite to arsenate on cryptomelane-type manganese oxide
Hou, Jingtao
Luo, Jinglin
Hu, Zhongqiu
Li, Yuanzhi
Mao, Mingyang
Song, Shaoxian
Liao, Qingling
Li, Qingzhu
[J]. CHEMICAL ENGINEERING JOURNAL, 2016, 306 : 597 - 606
[15] TEMP and copper cocatalyzed oxygenation of ketones with molecular oxygen: chemoselective synthesis of α-ketoesters
Huang, Xiaoqiang
Li, Xinwei
Zou, Miancheng
Pan, Jun
Jiao, Ning
[J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (04): : 354 - 359
[16] Vapour phase selective hydrogenation of benzaldehyde to benzyl alcohol using Cu supported Mg-Al hydrotalicite catalyst
Jayesh, T. B.
Itika, K.
Babu, G. V. Ramesh
Rao, K. S. Rama
Keri, R. S.
Jadhav, Arvind H.
Nagaraja, B. M.
[J]. CATALYSIS COMMUNICATIONS, 2018, 106 : 73 - 77
[17] Facile synthesis of Fe-modified manganese oxide with high content of oxygen vacancies for efficient airborne ozone destruction
Jia, Jingbo
Yang, Wenjuan
Zhang, Pengyi
Zhang, Junying
[J]. APPLIED CATALYSIS A-GENERAL, 2017, 546 : 79 - 86
[18] Alkali α-MnO2/NaxMnO2 collaboratively catalyzed ammoxidation-Pinner tandem reaction of aldehydes
Jia, Xiuquan
Ma, Jiping
Wang, Min
Li, Xiaofang
Gao, Jin
Xu, Jie
[J]. CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (20) : 7429 - 7436
[19] Efficient Aerobic Ruthenium-Catalyzed Oxidation of Secondary Alcohols by the Use of a Hybrid Electron Transfer Catalyst
Johnston, Eric V.
Karlsson, Erik A.
Tran, Lien-Hoa
Akermark, Bjorn
Backvall, Jan-E.
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (10) : 1971 - 1976
[20] Application of Ball Milling for Highly Selective Mechanochemical Polymorph Transformations
Kamali, Naghmeh
Gniado, Katarzyna
McArdle, Patrick
Erxleben, Andrea
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2018, 22 (07) : 796 - 802

← 1 2 3 4 5 6 →