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

[1] Mechanistic Insights on the Magnesium(II) Ion-Activated Reduction of Methyl Benzoylformate with Chelated NADH Peptide β-Lactam Models
Aizpurua, Jesus M.
Palomo, Claudio
Fratila, Raluca M.
Ferron, Pablo
Benito, Ana
Gomez-Bengoa, Enrique
Miranda, Jose I.
Santos, Jose I.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (17) : 6691 - 6702
[2] Photodegradation and inhibition of drug-resistant influenza virus neuraminidase using anthraquinone-sialic acid hybrids
Aoki, Yusuke
Tanimoto, Shuho
Takahashi, Daisuke
Toshima, Kazunobu
[J]. CHEMICAL COMMUNICATIONS, 2013, 49 (12) : 1169 - 1171
[3] Heterocyclic derivative syntheses by palladium-catalyzed oxidative cyclization -: Alkoxycarbonylation of substituted γ-oxoalkynes
Bacchi, A
Costa, M
Della Cà, N
Gabriele, B
Salerno, G
Cassoni, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) : 4971 - 4979
[4] 2-Oxo promoted hydrophosphonylation & aerobic intramolecular nucleophilic displacement reaction
Battula, Satyanarayana
Battini, Narsaiah
Singh, Deepika
Ahmed, Qazi Naveed
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (32) : 8637 - 8641
[5] Cu-Mn spinel oxide catalyzed synthesis of imidazo[1,2-a]pyridines through domino three-component coupling and 5-exo-dig cyclization in water
Bharate, Jaideep B.
Guru, Santosh K.
Jain, Shreyans K.
Meena, Samdarshi
Singh, Parvinder Pal
Bhushan, Shashi
Singh, Baldev
Bharate, Sandip B.
Vishwakarma, Ram A.
[J]. RSC ADVANCES, 2013, 3 (43): : 20869 - 20876
[6] Manganese oxide catalyzed synthesis of anti-HIV N-substituted benzimidazoles via a one-pot multistep process
Bi, Xiuru
Meng, Xu
Chen, Gexin
Chen, Baohua
Zhao, Peiqing
[J]. CATALYSIS COMMUNICATIONS, 2018, 116 : 27 - 31
[7] The role of various oxygen species in Mn-based layered double hydroxide catalysts in selective alcohol oxidation
Du, Yiyun
Wang, Qian
Liang, Xiao
Yang, Pengfei
He, Yufei
Feng, Junting
Li, Dianqing
[J]. CATALYSIS SCIENCE & TECHNOLOGY, 2017, 7 (19) : 4361 - 4365
[8] Preferential Carbon Monoxide Oxidation over Copper-Based Catalysts under InSitu Ball Milling
Eckert, Rene
Felderhoff, Michael
Schueth, Ferdi
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (09) : 2445 - 2448
[9] Catalytic properties of copper-manganese mixed oxides prepared by coprecipitation using tetramethylammonium hydroxide
Einaga, Hisahiro
Kiya, Akihiro
Yoshioka, Satoru
Teraoka, Yasutake
[J]. CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (10) : 3713 - 3722
[10] Microfluidic synthesis of α-ketoesters via oxidative coupling of acetophenones with alcohols under metal-free conditions
Guo, Shiyu
Dai, Zhongxue
Hua, Jiawei
Yang, Zhao
Fang, Zheng
Guo, Kai
[J]. REACTION CHEMISTRY & ENGINEERING, 2017, 2 (05): : 650 - 655

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