Details

Autor(en) / Beteiligte

• Galkin, Konstantin I.
• Gordeev, Evgeniy G.
• Ananikov, Valentine P.

Titel

Organocatalytic Deuteration Induced by the Dynamic Covalent Interaction of Imidazolium Cations with Ketones

Ist Teil von

• Advanced synthesis & catalysis, 2021-03, Vol.363 (5), p.1368-1378

Ort / Verlag

Heidelberg: Wiley Subscription Services, Inc

Erscheinungsjahr

2021

Quelle

Wiley Online Library Journals【Remote access available】

Beschreibungen/Notizen

• 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‐d6 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.