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MuraiCO_main_2019-12-08 ChemRxiv.pdf (1.74 MB)
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Ru-Catalyzed Carbonylative Murai Reaction: Directed C3-Acylation of Biomass-Derived 2-Formyl Heteroaromatics

preprint
submitted on 09.12.2019 and posted on 17.12.2019 by Roberto Sala, Fares Roudesly, Luis F. Veiros, Gianluigi Broggini, Julie Oble, Giovanni Poli

We describe here the carbonylative Murai reaction applied to 2-formylfurans, 2-formylpyrrols and 2-formylthiophenes. Thanks to the installation of removable imine directing groups, this acylation reaction takes place regioselectively at C3 position of the heterocyclopentadienes. It can be achieved by treating the two reaction partners with a catalytic amount of Ru3(CO)12, in toluene at 120-150 °C, after CO bubbling, at atmospheric pressure. DFT computations of the full catalytic cycle help in deciphering the mechanism of this transformation, and to rationalize the different behaviors depending on the nature of imine directing groups.

Funding

Horizon 2020 ERANet-LAC project CelluloseSynThech

CNRS, Sorbonne Université, Labex Michem (Investissements d'Avenir program, reference ANR-11-IDEX-0004-02).

Support through CMST COST Action, CA15106 (CHAOS)

Fundação para a Ciência e Tecnologia.

History

Email Address of Submitting Author

giovanni.poli@sorbonne-universite.fr

Institution

Sorbonne Université Campus Pierre et Marie Curie

Country

France

ORCID For Submitting Author

0000-0002-7356-1568

Declaration of Conflict of Interest

no conflict of interest to declare

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