化学
质子化
有机催化
酮
共价键
卡宾
烷基
催化作用
加合物
丙酮
选择性
有机化学
对映选择合成
组合化学
离子
作者
Konstantin I. Galkin,Evgeniy G. Gordeev,Valentine P. Ananikov
标识
DOI:10.1002/adsc.202001507
摘要
Abstract In this article, we suggest a new organocatalytic approach based on the dynamic covalent interaction of imidazolium cations with ketones. A reaction of N‐alkyl imidazolium salts with acetone‐ d 6 in the presence of oxygenated bases generates a dynamic organocatalytic system with a mixture of protonated carbene/ketone adducts acting as H/D exchange catalysts. The developed methodology of the pH‐dependent deuteration showed high selectivity of labeling and good chiral functional group tolerance. Here we report a unique methodology for efficient metal‐free deuteration, which enables labeling of various types of α‐acidic compounds without trace metal contamination. magnified image
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