Enantioselective <i>N</i>-Heterocyclic Carbene Catalysis via Acyl Azolium without Exogenous Oxidants
Jing Cao, Rachel M. Gillard, Azar Jahanbakhsh, Martin Breugst, David W. Lupton
Abstract
An approach to the α,β-unsaturated acyl azolium has been developed that exploits N-heterocyclic carbenes (NHCs) and acyl fluorides, without additional oxidants, bases, or preactivated pro-nucleophiles. These conditions have been applied in four classes of NHC-catalyzed reaction. In all cases, the expected products were produced with high yield and enantioselectivity, using two sets of closely related reaction conditions, without additional optimization.
Topics & Concepts
Enantioselective synthesisCarbeneCatalysisNucleophileChemistryYield (engineering)Combinatorial chemistryOrganic chemistryReaction conditionsMaterials scienceMetallurgyN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsSynthetic Organic Chemistry Methods