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An ionic liquid catalyzed probase method for one-pot synthesis of alpha,beta-unsaturated esters from esters and aldehydes under mild conditions
Wang, Gang1,2,3; Xu, Yiming4; Zhang, Suojiang2,3; Li, Zengxi1,2,3; Li, Chunshan1,2,3
2017-10-21
Source PublicationGREEN CHEMISTRY
ISSN1463-9262
Volume19Issue:20Pages:4838-4848
Abstract

A one-pot synthesis of alpha,beta-unsaturated esters from unactivated esters and aldehydes using strong bases, such as sodium alkoxide and potassium tert-butoxide, was reported. However, the ionic liquid (IL) catalyzed probase method for producing alpha,beta-unsaturated esters was not reported until now. In this work, a series of ILs with fluoride anions were firstly prepared and used as catalysts in combination with the probase N, O-bis(trimethylsilyl) acetamide (BSA) for the alpha,beta-unsaturated esters synthesis. This process could also be promoted through the introduction of another IL with Lewis acid sites. The yield and selectivity of the product could reach up to 84.2% and 95.0%, respectively, when [Bmim] F was used in combination with [Bmim] Cl/AlCl3 (the molar fraction of AlCl3 is 0.67). The mechanism investigation through GC-MS indicates that BSA would convert into onium amide, which acted as a strong base for a-H abstraction, with the catalysis of [Bmim] F. Meanwhile, [Bmim] Cl/AlCl3 played an important role in the condensation step between enolates and aldehydes. On the basis of mechanism insights, kinetic and thermodynamic studies were also carried out for a better understanding of this new route.

SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
DOI10.1039/c7gc02265d
Indexed BySCI
Language英语
WOS KeywordPHOSPHORUS OXIDE CATALYSTS ; ONIUM AMIDE BASES ; ALDOL-CONDENSATION ; ONE-STEP ; ACETIC-ACID ; TEMPERATURE ; FUNCTIONALIZATION ; TRIFLUOROMETHANE ; FORMALDEHYDE ; CHEMISTRY
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
Funding OrganizationNational Key Projects for Fundamental Research and Development of China(2016YFB0601303) ; National Science Fund for Excellent Young Scholars 4(21422607) ; National Natural Science Foundation of China(21676270 ; NSFC-Key Projects of Shanxi Coal Based Low Carbon Joint Foundation(U1610222) ; CAS/SAFEA International Partnership Program for Creative Research Teams ; 21576261)
WOS IDWOS:000413069600015
Citation statistics
Cited Times:2[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/23271
Collection湿法冶金清洁生产技术国家工程实验室
Affiliation1.Univ Chinese Acad Sci, Coll Chem & Chem Engn, Beijing 100049, Peoples R China
2.Chinese Acad Sci, Beijing Key Lab Green Proc & Engn, Key Lab Ion Liquids Clean Proc, Beijing 100190, Peoples R China
3.Chinese Acad Sci, State Key Lab Multiphase Complex Syst, Natl Key Lab Clean & Efficient Coking Technol, Inst Proc Engn, Beijing 100190, Peoples R China
4.East China Univ Sci & Technol, Sch Chem Engn, Shanghai 200237, Peoples R China
Recommended Citation
GB/T 7714
Wang, Gang,Xu, Yiming,Zhang, Suojiang,et al. An ionic liquid catalyzed probase method for one-pot synthesis of alpha,beta-unsaturated esters from esters and aldehydes under mild conditions[J]. GREEN CHEMISTRY,2017,19(20):4838-4848.
APA Wang, Gang,Xu, Yiming,Zhang, Suojiang,Li, Zengxi,&Li, Chunshan.(2017).An ionic liquid catalyzed probase method for one-pot synthesis of alpha,beta-unsaturated esters from esters and aldehydes under mild conditions.GREEN CHEMISTRY,19(20),4838-4848.
MLA Wang, Gang,et al."An ionic liquid catalyzed probase method for one-pot synthesis of alpha,beta-unsaturated esters from esters and aldehydes under mild conditions".GREEN CHEMISTRY 19.20(2017):4838-4848.
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