2019/09/05 by Ifzan Arshad, Aamer Saeed, Pervaiz Ali Channar +2 · 1 citation
Chemistry · #Organoboron and organosilicon chemistry #Catalytic Cross-Coupling Reactions #Synthetic Organic Chemistry Methods
paper · doi:10.1055/s-0039-1690676
openalex publication_date 2019/09/05 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/04
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.