2025/01/01 by Anthony P. Gee, Tiberiu‐Marius Gianga, Gabriele Kociok‐Köhn +2 · 1 voice
Chemistry · #Axial and Atropisomeric Chirality Synthesis #Molecular spectroscopy and chirality #Synthesis and Properties of Aromatic Compounds
paper · pdf · doi:10.1039/d5ra02520f
openalex publication_date 2025/01/01 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/02
Biaryls exhibiting axial chirality have been extensively exploited in fields such as asymmetric catalysis, but the biaryl linkage typically consists of benzenoid aromatic rings, with non-benzenoid biaryls being scarce. Here we report the first preparation of a (non-benzenoid) 1,1'-biazulene-2,2'-diol ("1,1'-BAzOL") in enantiopure form and determine its barrier to racemisation. Furthermore we transformed a 1,1'-biazulene-2,2'-diol into the corresponding 2,2'-bis(phosphonate), thereby demonstrating functional group interconversion through cross coupling and highlighting the potential for diversification.