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The Cu-Free Sonogashira Reaction Mechanism

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Part of the Springer Theses book series (Springer Theses)

Abstract

The palladium-catalyzed Sonogashira reaction is one of the most important and widely used methods for preparing arylacetylenes and conjugated enynes, [1, 2, 3, 4, 5, 6] which are precursors for natural products, pharmaceuticals, and materials with specialized optical and electronic properties [7, 8, 9, 10, 11, 12]. The purpose of the work reported in this chapter was to weigh up the reaction mechanisms proposed in the literature and possible alternative pathways using a general model of the typical Pd-catalyzed copper-free Sonogashira reaction. To this aim, the Gibbs energy profiles of the different mechanistic proposals were computed by means of DFT calculations. Additionally, the effect of the electronic nature of the alkyne’s substituents over all the reaction pathways was also analyzed. This was examined for a set of substituents combining theoretical calculations and experiments. This work was carried out in collaboration with the experimental group of Prof. Carmen N\(\acute{\mathrm{a}}\)jera at the Universidad de Alicante.

Keywords

Energy Barrier Ionic Mechanism Phosphine Ligand Anionic Mechanism Reductive Elimination 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Springer International Publishing Switzerland 2013

Authors and Affiliations

  1. 1.Department of ChemistryAutonomous University of BarcelonaCerdanyola del VallèsSpain

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