Synthesis and structure of m-terphenyl-based cyclophanes with nitrogen intra-annular functional groups.
[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.
Camacho
Drexel H
DH
Chemistry Department, University of California-Irvine, Irvine, California 92697-2025, USA.
Salo
Eric V
EV
Guan
Zhibin
Z