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Article Dans Une Revue Green Chemistry Année : 2017

Continuous flow ring-closing metathesis, an environmentally-friendly route to 2,5-dihydro-1H-pyrrole-3-carboxylates

Résumé

2,5-Dihydro-1H-pyrrole-3-carboxylates are important building blocks for the synthesis of high value pyrroles and pyrroloquinoline derivatives with interesting biological activities. The use of continuous flow allowed us to perform a key synthetic step, namely ruthenium-catalyzed ring-closing metathesis, with a residence time of 1 min at 120°C. Dimethyl carbonate, a green solvent, was demonstrated for the first time to be an excellent solvent for this reaction in continuous flow. The continuous flow conditions proved to be general and the scale-up of this reaction was not only possible, but also highly efficient. Conversion of 10 grams of diene was realized in 37 minutes under continuous flow, yielding the desired heterocycle in 91% yield. Fig. 1 Pharmaceutical drugs synthesized using olefin metathesis. † Electronic supplementary information (ESI) available. See
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hal-02385309 , version 1 (04-01-2021)

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Marcin Drop, Xavier Bantreil, Katarzyna Grychowska, Gilbert Umuhire Mahoro, Evelina Colacino, et al.. Continuous flow ring-closing metathesis, an environmentally-friendly route to 2,5-dihydro-1H-pyrrole-3-carboxylates. Green Chemistry, 2017, 19 (7), pp.1647-1652. ⟨10.1039/c7gc00235a⟩. ⟨hal-02385309⟩
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