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Issue 7, 2017
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Continuous flow ring-closing metathesis, an environmentally-friendly route to 2,5-dihydro-1H-pyrrole-3-carboxylates

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Abstract

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.

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

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Article information


Submitted
19 Jan 2017
Accepted
15 Feb 2017
First published
16 Feb 2017

Green Chem., 2017,19, 1647-1652
Article type
Communication

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

M. Drop, X. Bantreil, K. Grychowska, G. U. Mahoro, E. Colacino, M. Pawłowski, J. Martinez, G. Subra, P. Zajdel and F. Lamaty, Green Chem., 2017, 19, 1647
DOI: 10.1039/C7GC00235A

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