HFIP Mediates a Direct C−C Coupling between Michael Acceptors and Eschenmoser's salt
Miran Lemmerer, Margaux Riomet, Ricardo Meyrelles, Boris Maryasin, Leticia González, Nuno Maulide
Abstract
A direct C-C coupling process that merges Michael acceptors and Eschenmoser's salt is presented. Although reminiscent of the Morita-Baylis-Hillman reaction, this process requires no Lewis base catalyst. The underlying mechanism was unveiled by a combination of kinetic, isotopic labelling experiments as well as computational investigations, which showcased the critical role of HFIP as a superior mediator for proton-transfer events as well as the decisive role of the halide counterion.
Topics & Concepts
CounterionChemistryMichael reactionSalt (chemistry)Lewis acids and basesCatalysisHalideCombinatorial chemistryStereochemistryComputational chemistryOrganic chemistryIonPhotoreceptor and optogenetics researchNeuroscience and Neuropharmacology ResearchNicotinic Acetylcholine Receptors Study