One-step synthesis of [15]paracyclophane and [16]paracyclophane via Pd-catalyzed C(sp2)–C(sp3) coupling and the cyclohexane-encapsulating crystal structure of [16]paracyclophane

Abstract

Abstract Macrocycles consisting of methylene-bridged aromatic rings had been synthesized by aromatic electrophilic substitution reactions, thus limiting the substrates to electron-rich aromatic compounds. In this work, we developed a novel method for 1-step synthesis of [15]paracyclophane (PCP) and [16]PCP by the self-condensation of 4-bromobenzyl bromide via a Pd-catalyzed desulfinative coupling reaction between C(sp2) and C(sp3) carbon atoms. In the crystal structure, [16]PCP encapsulated cyclohexane and formed a 1D columnar structure