An efficient, eco-friendly and sustainable tandem oxidative amidation of alcohols with amines catalyzed by heteropolyanion-based ionic liquids via a bifunctional catalysis process

被引:16
作者
Fu, Renzhong [1 ]
Yang, Yang [1 ]
Feng, Wei [1 ]
Ge, Qiuxia [1 ]
Feng, Yan [1 ]
Zeng, Xiaojun [1 ]
Chai, Wen [1 ]
Yi, Jun [1 ]
Yuan, Rongxin [1 ]
机构
[1] Changshu Inst Technol, Jiangsu Lab Adv Funct Mat, Sch Chem & Mat Engn, Changshu 215500, Peoples R China
基金
中国国家自然科学基金;
关键词
Amide; Ionic liquid; Microwave-assisted; Oxidative amidation; Solvent-free condition; AMIDE BOND FORMATION; BENZYL ALCOHOLS; ORGANIC-SYNTHESIS; POLYOXOMETALATE; MICROWAVE; EPOXIDATION; ALDEHYDES; TRANSAMIDATION; CARBOXAMIDES; PEPTIDES;
D O I
10.1016/j.tet.2016.11.002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient, eco-friendly and sustainable method for the tandem oxidative amidation of alcohols with amines has been reported. Using heteropolyanion-based ionic liquids as the catalyst and tert-butyl hydroperoxide as the oxidant, this amidation reaction is operationally straightforward and provides a series of primary, secondary and tertiary amides derivatives in moderate to good yields. Solvent-free media, microwave-promoted conditions and reusability of catalysts are the main highlights. Further, the proposed bifunctional catalysis mechanistic pathway has been briefly investigated in this report. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:8319 / 8326
页数:8
相关论文
共 80 条
[1]   Metal-catalysed approaches to amide bond formation [J].
Allen, C. Liana ;
Williams, Jonathan M. J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3405-3415
[2]   Superparamagnetic Fe(OH)3@Fe3O4 Nanoparticles: An Efficient and Recoverable Catalyst for Tandem Oxidative Amidation of Alcohols with Amine Hydrochloride Salts [J].
Arefi, Marzban ;
Saberi, Dariush ;
Karimi, Meghdad ;
Heydari, Akbar .
ACS COMBINATORIAL SCIENCE, 2015, 17 (06) :341-347
[3]   Direct oxidative amidation of benzyl alcohols using EDTA@Cu(II) functionalized superparamagnetic nanoparticles [J].
Azizi, Kobra ;
Karimi, Meghdad ;
Nikbakht, Fatemeh ;
Heydari, Akbar .
APPLIED CATALYSIS A-GENERAL, 2014, 482 :336-343
[4]   Alternative energy input: mechanochemical, microwave and ultrasound-assisted organic synthesis [J].
Baig, R. B. Nasir ;
Varma, Rajender S. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (04) :1559-1584
[5]   Iron/Caffeine as a Catalytic System for Microwave-Promoted Benzamide Formation [J].
Bantreil, Xavier ;
Navals, Pauline ;
Martinez, Jean ;
Lamaty, Frederic .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (02) :417-422
[6]   Iron-catalyzed benzamide formation. Application to the synthesis of moclobemide [J].
Bantreil, Xavier ;
Kanfar, Nasreddine ;
Gehin, Nicolas ;
Golliard, Ethan ;
Ohlmann, Pauline ;
Martinez, Jean ;
Lamaty, Frederic .
TETRAHEDRON, 2014, 70 (34) :5093-5099
[7]  
Bode JW, 2006, CURR OPIN DRUG DISC, V9, P765
[8]   A liquid derivative of 12-tungstophosphoric acid with unusually high conductivity [J].
Bourlinos, AB ;
Raman, K ;
Herrera, R ;
Zhang, Q ;
Archer, LA ;
Giannelis, EP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (47) :15358-15359
[9]   An eco-benign and highly efficient procedure for N-acylation catalyzed by heteropolyanion-based ionic liquids using carboxylic acid under solvent-free conditions [J].
Chen, Zhikai ;
Fu, Renzhong ;
Chai, Wen ;
Zheng, Hao ;
Sun, Lin ;
Lu, Qiang ;
Yuan, Rongxin .
TETRAHEDRON, 2014, 70 (13) :2237-2245
[10]   Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water [J].
Cho, SH ;
Yoo, EJ ;
Bae, L ;
Chang, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) :16046-16047