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RESEARCH PRODUCT
Sustainable Approach to Waste-Minimized Sonogashira Cross-Coupling Reaction Based on Recoverable/Reusable Heterogeneous Catalytic/Base System and Acetonitrile Azeotrope
Luigi VaccaroStefano SantoroMichelangelo GruttadauriaGiacomo StrappavecciaLucia Anna BivonaLucia Anna BivonaVadym KozellMichael MclaughlinCarmela Aprilesubject
Green chemistryAzeotrope media; Green chemistry; Heterogeneous catalysis; Sonogashira reaction; Waste minimization; Chemistry (all); Environmental Chemistry; Chemical Engineering (all); Renewable Energy Sustainability and the EnvironmentGeneral Chemical EngineeringWaste minimizationchemistry.chemical_elementSonogashira coupling010402 general chemistryHeterogeneous catalysis01 natural sciencesCoupling reactionCatalysisHeterogeneous catalysichemistry.chemical_compoundEnvironmental ChemistryOrganic chemistryChemical Engineering (all)Renewable EnergyAcetonitrileHeterogeneous catalysisSustainability and the Environment010405 organic chemistryRenewable Energy Sustainability and the EnvironmentChemistry (all)Settore CHIM/06 - Chimica OrganicaGeneral ChemistryAzeotrope mediaCombinatorial chemistry0104 chemical scienceschemistryGreen chemistryLeaching (metallurgy)Sonogashira reactionPalladiumdescription
In this contribution, we present a chemically efficient and sustainable protocol for the palladium-catalyzed copper-free Sonogashira cross-coupling reaction, based on the use of a heterogeneous catalytic system. This consists in the combination of a palladium catalyst on highly cross-linked thiazolidine network on silica and a polystyrene-supported base. The solid catalyst/base system acts as a palladium scavenger avoiding leaching of the metal and consequent product contamination. The reaction can be conducted in safe and easily recoverable acetonitrile/water azeotrope as reaction medium. This proved to be an efficient greener alternative to the classic toxic aprotic media commonly used in cross-coupling reaction, such as DMF and NMP. Acetonitrile/water azeotrope could be easily recovered and reused allowing the minimization of waste production. Our approach, based on the use of both a supported base and a supported catalyst, has proven to be efficient for the waste reduction, as proved by the low E-factor values achieved.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-01-01 | ACS Sustainable Chemistry and Engineering |