A biomass-derived safe medium to replace toxic dipolar solvents and access cleaner Heck coupling reactions

Giacomo Strappaveccia, Ermal Ismalaj, Chiara Petrucci, Daniela Lanari, Assunta Marrocchi, Martin Drees, Antonio Facchetti*, Luigi Vaccaro

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

121 Scopus citations

Abstract

γ-Valerolactone (GVL) is an excellent reaction medium, derived from biomasses, which can replace classic dipolar aprotic media such as DMF or NMP. In this contribution, we have investigated the use of GVL in the palladium-catalyzed Heck reaction and accessed the clean synthesis of several small molecules. Furthermore, we optimized a GVL-based protocol to synthesize a poly(phenylenevinylene) (PPV) derivative in high yields and purity, and with very low Pd-content. Finally, we demonstrated that GVL is superior to conventional dipolar media in terms of controlling palladium impurities, which may influence the performance of certain optoelectronic devices such as organic solar cells and field-effect transistors.

Original languageEnglish (US)
Pages (from-to)365-372
Number of pages8
JournalGreen Chemistry
Volume17
Issue number1
DOIs
StatePublished - Jan 1 2015

ASJC Scopus subject areas

  • Environmental Chemistry
  • Pollution

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