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Organocatalytic Deuteration Induced by the Dynamic Covalent Interaction of Imidazolium Cations with Ketones
Author(s) -
Galkin Konstantin I.,
Gordeev Evgeniy G.,
Ananikov Valentine P.
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001507
Subject(s) - chemistry , protonation , organocatalysis , ketone , covalent bond , carbene , alkyl , catalysis , adduct , acetone , selectivity , organic chemistry , enantioselective synthesis , combinatorial chemistry , ion
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.