HFIP Mediates a Direct C−C Coupling between Michael Acceptors and Eschenmoser's salt

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 experi...

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Detalles Bibliográficos
Autores principales: Lemmerer, Miran, Riomet, Margaux, Meyrelles, Ricardo, Maryasin, Boris, González, Leticia, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9306631/
https://www.ncbi.nlm.nih.gov/pubmed/34813137
http://dx.doi.org/10.1002/anie.202109933
Descripción
Sumario: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.

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