Affiliation:
1. Univ Rennes CNRS, ISCR – UMR6226 FR-35000 Rennes France
Abstract
AbstractIn order to obtain new supramolecular ligands that build up around a zinc‐porphyrin scaffold, we envisioned to access sulfonyl triazole intermediates by well‐known copper‐catalyzed click reactions. Unexpectedly, these triazole intermediates do not form due to the presence of the zinc‐porphyrin moiety at close proximity of the active copper species. Indeed, the copper catalyst undergoes a different chemo‐selective reaction pathway reacting with traces of alcohols or water from the media that behave as effective nucleophiles leading to sulfonyl imidates or sulfonyl amides covalently connected to the zinc‐porphyrin. We show that copper‐catalyzed click reactions can follow different reaction mechanisms when the catalytic events occur at close proximity of a zinc‐porphyrin unit which likely acts as a Lewis acid to stabilize otherwise inaccessible reaction intermediates.
Funder
Agence Nationale de la Recherche
Subject
Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Drug Discovery,Biochemistry,Catalysis
Cited by
2 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献