Sustainable Approach to Waste-Minimized Sonogashira Cross-Coupling Reaction Based on Recoverable/Reusable Heterogeneous Catalytic/Base System and Acetonitrile Azeotrope

Michelangelo Gruttadauria, Lucia Anna Bivona, Stefano Santoro, Lucia Anna Bivona, Giacomo Strappaveccia, Vadym Kozell, Michael Mclaughlin, Luigi Vaccaro, Carmela Aprile

Risultato della ricerca: Articlepeer review

30 Citazioni (Scopus)

Abstract

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.
Lingua originaleEnglish
pagine (da-a)7209-7216
Numero di pagine8
RivistaACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume4
Stato di pubblicazionePublished - 2016

All Science Journal Classification (ASJC) codes

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  • ???subjectarea.asjc.2300.2304???
  • ???subjectarea.asjc.1500.1500???
  • ???subjectarea.asjc.2100.2105???

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