[gamma]-Valerolactone as an alternative biomass-derived medium for the Sonogashira reaction
Green Chem., 2015, Advance Article
DOI: 10.1039/C4GC01728E, PaperDOI: 10.1039/C4GC01728E
Giacomo Strappaveccia, Lorenzo Luciani, Elena Bartollini, Assunta Marrocchi, Ferdinando Pizzo, Luigi Vaccaro
[gamma]-Valerolactone (GVL) can be used as an efficient and practical alternative to the banned and commonly used dipolar aprotic solvents.
γ-Valerolactone (GVL) can be used as an efficient and practical alternative to the banned and commonly used dipolar aprotic solvents. In this contribution GVL has been used as a non-toxic, biodegradable, biomass-derived medium, for the definition of a simple and general protocol for the Sonogashira cross-coupling reaction. The chemical efficiency of GVL as a medium is excellent and the best results have been obtained using DABCO as the base allowing the isolation of products 3a–q in 60–96% yields. These results represent an example which proves that biomass-derived safer solvents can be used efficiently in common transformations reaching higher greenness/sustainability as well as high chemical efficiency.