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RESEARCH PRODUCT
An E-Factor Minimized Protocol for a Sustainable and Efficient Heck Reaction in Flow
Michelangelo GruttadauriaLuigi VaccaroFrancesco GiacaloneChiara PetrucciGiacomo StrappavecciaFerdinando Pizzosubject
Green chemistrygreen chemistryRenewable Energy Sustainability and the EnvironmentChemistryGeneral Chemical Engineeringchemistry.chemical_elementcross-coupling. palladiumSettore CHIM/06 - Chimica OrganicaGeneral ChemistryFlow chemistryHeterogeneous catalysisCatalysischemistry.chemical_compoundChemical engineeringHeck reactioncontinuous flowEnvironmental ChemistryOrganic chemistryLeaching (metallurgy)C-C couplingAcetonitrilecross-coupling. palladium green chemistryPalladiumPalladiumdescription
A highly sustainable and waste-minimized protocol for Heck coupling has been defined. Optimal conditions have been defined by exploiting a heterogeneous catalyst based on supported ionic liquid-like phases featuring high Pd loading (10 wt %) and by optimizing its efficiency in a recoverable green reaction medium (acetonitrile/water azeotrope). Pure products 4a–l and 6a–h have been isolated chromatography-free in high yields (74–99%) and with extremely low environmental factor (E-factor) values (2.3–5.0). With the application of flow technology, the selected heterogeneous base and Pd catalyst have been fully recovered and reused, and minimum palladium leaching allowed for isolation of the final products with low residual palladium content (<5 ppm) without any purification step.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-10-23 | ACS Sustainable Chemistry & Engineering |