Computational Study of Copper-Free Sonogashira Cross-Coupling Reaction
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Abstract
The copper-free Sonogashira cross-coupling reaction consisting of oxidative addition, <i>cis–trans</i> isomerization, deprotonation, and reductive elimination was computationally modeled using the DFT B97D/cc-pVDZ method for reaction between phenyl bromide and phenylacetylene. Tetrakis(triphenylphosphano)palladium was used as a catalyst and <i>sec</i>-butylamine as a base. The reaction mechanism was studied in dichloromethane solution. Oxidative addition proceeds through the biligated pathway, and the catalytically active palladium species is Pd(PPh<sub>3</sub>)<sub>3</sub>. Amines, present in the reaction mixture, can inhibit oxidative addition by coordinating to Pd(PPh<sub>3</sub>)<sub>3</sub>
