NHC-Catalyzed, Microwave-Assisted and Base-Dependent Reactions of Substituted Cinnamaldehydes Towards γ-Lactones or Saturated Esters

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2024-11-06 DOI:10.1002/ejoc.202401047
Victoria Magrioti, Evanthia Papadaki, Antonia Kapoti, Roza Leitourgaki, Aikaterini Vogiatzi
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Abstract

N-Heterocyclic carbenes (NHCs) generated from imidazolium, imidazopyridinium and imidazoquinolinium hydrochlorides in situ using base and microwave irradiation were employed as organocatalysts to yield homoenolates from cinnamaldehyde and its aryl-substituted analogs. Depending on the catalytic base either γ-lactones were prepared when the strong base tBuOK was used or the corresponding saturated ethyl 3-aryl propionates were synthesized with the milder DIPEA base. Novel imidazopyridinium and imidazoquinolinium hydrochlorides were synthesized and were compared to commercially available NHCs IMes and IDip for their catalytic activity. The optimum reaction conditions were established using IMes and the broad scope of both reactions was investigated using the 4 most efficient NHCs.
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NHC 催化、微波辅助和碱依赖的取代肉桂醛与γ-内酯或饱和酯的反应
利用碱和微波辐照从咪唑鎓、咪唑吡啶鎓和咪唑喹啉鎓盐酸盐原位生成的 N-杂环碳烯(NHC)作为有机催化剂,从肉桂醛及其芳基取代的类似物中生成均烯醇酯。根据催化碱的不同,要么使用强碱 tBuOK 制备出 γ-内酯,要么使用较温和的 DIPEA 碱合成相应的饱和 3-芳基丙酸乙酯。合成了新型咪唑吡啶鎓和咪唑喹啉鎓盐酸盐,并与市售的 NHC IMes 和 IDip 进行了催化活性比较。使用 IMes 确定了最佳反应条件,并使用 4 种最有效的 NHC 研究了这两种反应的广泛范围。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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