Journal of Organic Chemistry 2010-06-04

Glucose as a clean and renewable reductant in the Pd-nanoparticle-catalyzed reductive homocoupling of bromo- and chloroarenes in water.

Antonio Monopoli, Vincenzo Calò, Francesco Ciminale, Pietro Cotugno, Carlo Angelici, Nicola Cioffi, Angelo Nacci

Index: J. Org. Chem. 75(11) , 3908-11, (2010)

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Abstract

An efficient and highly sustainable Ullmann-type homocoupling of bromo- and chloroarenes, including the more challenging electron-rich chloroarenes (e.g., 4-chloroanisole), catalyzed by in situ generated Pd colloids, is carried out in aqueous medium under relatively mild conditions (temperatures ranging from 40 to 90 degrees C). Glucose is used as a clean and renewable reductant, while tetrabutylammonium hydroxide (TBAOH) acts as base, surfactant, and phase-transfer agent, creating a favorable environment for the catalyst. Pd nanoparticle sizes, morphology, and chemical composition are ascertained by TEM and XPS analyses.