Synthesis of a Contrapositionally Substituted Cyclohexa-meta-phenylene: A Ready-to-Use Precursor for Cyclohexa-meta-phenylene-Based Materials

Synlett DOI: 10.1055/s-0039-1690676 A contrapositionally substituted derivative of cyclohexa-meta-phenylene ([6]CMP) was synthesized by an intramolecular Yamamoto coupling reaction of an appropriate terphenyl unit containing a trimethylsilyl substituent. Iododesilylation of the trimethylsilyl groups of the product with iodine monochloride was used to incorporate iodo groups, an important functionality for metal-catalyzed coupling reactions. The iodo groups were also converted into a (pinacolato)boryl groups, another important functionality for coupling reactions. The diborylated [6]CMP is expected to be a versatile potential comonomer and a precursor for the synthesis of CMP-based materials. The synthetic route to the disubstituted [6]CMP included lithiation, Pd-catalyzed borylation, Suzuki coupling, and Yamamoto coupling. The structure of the product was established by NMR spectroscopy and mass spectrometry. [...] © Georg Thieme Verlag Stuttgart · New YorkArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - September 4, 2019 Category: Chemistry Authors: Arshad, Ifzan Saeed, Aamer Channar, Pervaiz Ali Shehzadi, Syeda Aaliya Irfan, Rana Muhammad Tags: letter Source Type: research