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

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 selectiv...

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Bibliographic Details
Published in:Tetrahedron 1998-08, Vol.54 (32), p.9401-9414
Main Authors: Pilard, J.F., Marchand, G., Simonet, J.
Format: Article
Language:English
Subjects:
cathodic cleavage
combinatorial chemistry
nitrogen-sulfur bonds
Solid interface synthesis
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Summary: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. Electrogenerated polythiophenes were tested as a Merrifield-like resin for the anchoring of amine functions together with deprotection processes.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(98)00580-8