Amberlyst-15 as a new and reusable catalyst for regioselective ring-opening reactions of epoxides to β-alkoxy alcohols

被引:91
作者
Liu, Yu-Heng [1 ]
Liu, Qiu-Shuang [1 ]
Zhang, Zhan-Hui [1 ]
机构
[1] Hebei Normal Univ, Coll Chem & Mat Sci, Shijiazhuang 050016, Peoples R China
基金
中国国家自然科学基金;
关键词
Amberlyst-15; Heterogeneous catalyst; Ring opening; Epoxide; beta-Alkoxy alcohol; Ultrasound;
D O I
10.1016/j.molcata.2008.09.003
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
Amberlyst-15 serves as an inexpensive, effective, and environmental friendly heterogeneous catalyst for the regioselective ring-opening of epoxides by primary, secondary and tertiary alcohols, resulted in the formation of beta-alkoxy alcohols in 40-95% yields under ultrasound irradiation. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:42 / 46
页数:5
相关论文
共 44 条
[1]   LONG-ACTING DIHYDROPYRIDINE CALCIUM-ANTAGONISTS .1. 2-ALKOXYMETHYL DERIVATIVES INCORPORATING BASIC SUBSTITUENTS [J].
ARROWSMITH, JE ;
CAMPBELL, SF ;
CROSS, PE ;
STUBBS, JK ;
BURGES, RA ;
GARDINER, DG ;
BLACKBURN, KJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (09) :1696-1702
[2]   Copper(II) tetrafluoroborate catalyzed ring-opening reaction of epoxides with alcohols at room temperature [J].
Barluenga, J ;
Vázquez-Villa, H ;
Ballesteros, A ;
González, JM .
ORGANIC LETTERS, 2002, 4 (17) :2817-2819
[3]   Aluminium triflate: a remarkable Lewis acid catalyst for the ring opening of epoxides by alcohols [J].
Bradley, D ;
Williams, G ;
Lawton, M .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (18) :3269-3272
[4]   An efficient direct conversion of THP ethers into acetates using Amberlyst-15 [J].
Das, B ;
Reddy, MR ;
Reddy, KR ;
Ramu, R ;
Thirupathi, P .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 248 (1-2) :185-188
[5]   Amberlyst-15: An efficient reusable heterogeneous catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines [J].
Das, B ;
Thirupathi, P ;
Mahender, I ;
Reddy, VS ;
Rao, YK .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 247 (1-2) :233-239
[6]   Application of heterogeneous solid acid catalysts for Friedlander synthesis of quinolines [J].
Das, Biswanath ;
Damodar, Kongara ;
Chowdhury, Nikhil ;
Kumar, Rathod Aravind .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 274 (1-2) :148-152
[7]   Highly regio- and stereoselective ring-opening of epoxides and aziridines with sodium azide using ammonium-12-molybdophosphate [J].
Das, Biswanath ;
Reddy, Vtukuri Saidi ;
Krishnaiah, Maddeboina ;
Rao, Yerra Koteswara .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 270 (1-2) :89-92
[8]   Amberlyst-15:: A mild, efficient and reusable heterogeneous catalyst for Michael addition of pyrroles to α,β-unsaturated ketones [J].
Das, Biswanath ;
Damodar, Kongara ;
Chowdhury, Nikhil .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 269 (1-2) :81-84
[9]   Amberlyst-15: An efficient reusable heterogeneous catalyst for aza-Michael reactions under solvent-free conditions [J].
Das, Biswanath ;
Chowdhury, Nikhil .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 263 (1-2) :212-215
[10]   A convenient highly stereoselective synthesis of allyl amides from Baylis-Hillman adducts using Amberlyst-15 as a heterogeneous reusable catalyst [J].
Das, Biswanath ;
Majhi, Anjoy ;
Banerjee, Joydeep ;
Chowdhury, Nikhil .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 260 (1-2) :32-34