Polypyrrole-supported graphite felt for Heck reaction in solid phase synthesis

Abstract

Substrate immobilization on graphite felt for solid phase Heck reaction was achieved by electrochemical polymerization of the substrate precursor containing a pyrrole side chain, where the amount of substrate on the electrode surface was easily controlled by the number of repeated cyclic voltammetric scanning. Couplings between olefins and the 4-iodobenzoic acid-modified graphite felt electrode or aromatic halides and the 4-vinylbenzoic acid-modified graphite felt electrode in the presence of palladium catalyst proceeded smoothly in satisfactory yields. The used substrate-modified electrode was reproduced by the treatment of used electrode with activated ester species of 4-vinylbenzoic acid, and was able to be recycled to Heck reaction in solid phase synthesis.