Chemical synthesis at solid interfaces. On the use of conducting polythiophenes equipped of adequate linkers allowing a facile and highly selective cathodic S-N bond scission with a fully regenerating resin process

Article abstract of DOI:10.1016/S0040-4020(98)00580-8

Electrogenerated polythiophenes were evaluated as Merrifield-like resins for the anchoring of amine functions together with deprotection processes. Suitable linkers were terminated with a fully regenerable aromatic sulfonamide moiety. The S-N bond was cleaved to liberate the amine with high selectivity under very mild conditions by cathodic means with amine liberation. Moreover a facile recycling process of the resin allows the further grafting of various amine functions.