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

26 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

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment

Fingerprint Entra nei temi di ricerca di 'Sustainable Approach to Waste-Minimized Sonogashira Cross-Coupling Reaction Based on Recoverable/Reusable Heterogeneous Catalytic/Base System and Acetonitrile Azeotrope'. Insieme formano una fingerprint unica.

Cita questo