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Microwave-assisted synthesis of hydroxymethyl ketones using azolium-2-carboxylate zwitterions as catalyst precursors
Tetrahedron ( IF 2.1 ) Pub Date : 2017-11-11 , DOI: 10.1016/j.tet.2017.11.024
Evanthia Papadaki , Lionel Delaude , Victoria Magrioti

Following an initial screening of six common imidazolium, imidazolinium, and dithiolium salts in the presence of a base, 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IDip) and 1,3-dimesitylimidazolin-2-ylidene (SIMes) were identified as promising organocatalysts for the microwave-assisted synthesis of hydroxymethyl ketones from aldehydes and paraformaldehyde. The azolium-2-carboxylate zwitterions IDip·CO2 and SIMes·CO2 were then tested as single-component N-heterocyclic carbene (NHC) precursors in the hydroxymethylation of heptanal and benzaldehyde. The latter adduct was an efficient precatalyst for the two reactions. It was successfully applied to a broad range of aliphatic and aromatic substrates (14 examples, 10–97% yields).



中文翻译:

微波辅助合成2-甲基偶氮鎓两性离子作为催化剂前体的羟甲基酮

在存在碱的情况下,初步筛选了六种常见的咪唑鎓盐,咪唑啉鎓盐和二硫鎓盐之后,1,3-双(2,6-二异丙基苯基)咪唑-2-亚胺基(IDip)和1,3-二甲酰亚胺咪唑啉-2-亚砜(SIMes)被认为是微波从醛和多聚甲醛合成羟甲基酮的有前途的有机催化剂。然后,在庚醛和苯甲醛的羟甲基化反应中,将2-羧酸二氮唑两性离子IDip·CO 2和SIMes·CO 2作为单组分N-杂环卡宾(NHC)前体进行了测试。后者的加合物是两个反应的有效预催化剂。它已成功应用于各种脂族和芳族底物(14个实例,产率10-97%)。

更新日期:2017-11-11
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