Synthesis and Structure of<i>m</i>-Terphenyl-Based Cyclophanes with Nitrogen Intra-annular Functional Groups

Abstract

[structure: see text] Herein we describe an efficient synthesis of cyclophanes comprised of intra-annular nitrogen functional groups through a template-promoted cyclization by ring-closing metathesis (RCM). The synthesis proceeds through condensation of meta-styryl anilines with acenaphthenequinone to form the templates, followed by RCM with Grubb's second-generation catalyst to afford cyclophanes with internal alpha-diimine functionality. Prolonged hydrogenation efficiently removes the template to provide a macrocycle containing the diamine functionality.