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

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.

SUBMITTER: Lemmerer M

PROVIDER: S-EPMC9306631 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature

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

Lemmerer Miran M Riomet Margaux M Meyrelles Ricardo R Maryasin Boris B González Leticia L Maulide Nuno N

Angewandte Chemie (International ed. in English) 20220203 11

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. ...[more]

PMID: 34813137

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