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MuraiCO_main_2019-12-08 ChemRxiv.pdf (1.74 MB)

Ru-Catalyzed Carbonylative Murai Reaction: Directed C3-Acylation of Biomass-Derived 2-Formyl Heteroaromatics

submitted on 09.12.2019, 15:41 and posted on 17.12.2019, 11:29 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.


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.


Email Address of Submitting Author


Sorbonne Université Campus Pierre et Marie Curie



ORCID For Submitting Author


Declaration of Conflict of Interest

no conflict of interest to declare