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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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
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author Lemmerer, Miran
Riomet, Margaux
Meyrelles, Ricardo
Maryasin, Boris
González, Leticia
Maulide, Nuno
author_facet Lemmerer, Miran
Riomet, Margaux
Meyrelles, Ricardo
Maryasin, Boris
González, Leticia
Maulide, Nuno
author_sort Lemmerer, Miran
collection PubMed
description 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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spelling pubmed-93066312022-07-28 HFIP Mediates a Direct C−C Coupling between Michael Acceptors and Eschenmoser's salt Lemmerer, Miran Riomet, Margaux Meyrelles, Ricardo Maryasin, Boris González, Leticia Maulide, Nuno Angew Chem Int Ed Engl Research Articles 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. John Wiley and Sons Inc. 2022-02-03 2022-03-07 /pmc/articles/PMC9306631/ /pubmed/34813137 http://dx.doi.org/10.1002/anie.202109933 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Lemmerer, Miran
Riomet, Margaux
Meyrelles, Ricardo
Maryasin, Boris
González, Leticia
Maulide, Nuno
HFIP Mediates a Direct C−C Coupling between Michael Acceptors and Eschenmoser's salt
title HFIP Mediates a Direct C−C Coupling between Michael Acceptors and Eschenmoser's salt
title_full HFIP Mediates a Direct C−C Coupling between Michael Acceptors and Eschenmoser's salt
title_fullStr HFIP Mediates a Direct C−C Coupling between Michael Acceptors and Eschenmoser's salt
title_full_unstemmed HFIP Mediates a Direct C−C Coupling between Michael Acceptors and Eschenmoser's salt
title_short HFIP Mediates a Direct C−C Coupling between Michael Acceptors and Eschenmoser's salt
title_sort hfip mediates a direct c−c coupling between michael acceptors and eschenmoser's salt
topic Research Articles
url 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
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