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

Authors :
Drop, Marcin
Bantreil, Xavier
Grychowska, Katarzyna
Mahoro, Gilbert Umuhire
Colacino, Evelina
Pawłowski, Maciej
Martinez, Jean
Subra, Gilles
Zajdel, Pawel
Lamaty, Frédéric
Source :
Green Chemistry; 4/7/2017, Vol. 19 Issue 7, p1647-1652, 6p
Publication Year :
2017

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. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
14639262
Volume :
19
Issue :
7
Database :
Complementary Index
Journal :
Green Chemistry
Publication Type :
Academic Journal
Accession number :
122287272
Full Text :
https://doi.org/10.1039/c7gc00235a