Gee Anthony P, Gianga Tiberiu-M, Kociok-Köhn Gabriele, Pantoş G Dan, Lewis Simon E
Department of Chemistry, University of Bath Bath BA2 7AY UK
Physical Structure Characterization Facility, University of Bath Bath BA2 7AY UK.
RSC Adv. 2025 May 16;15(19):14881-14892. doi: 10.1039/d5ra02520f. eCollection 2025 May 6.
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.
具有轴手性的联芳基化合物已在不对称催化等领域得到广泛应用，但联芳基连接通常由苯型芳环组成，非苯型联芳基化合物很少见。在此，我们报道了对映体纯形式的（非苯型）1,1'-二薁-2,2'-二醇（“1,1'-BAzOL”）的首次制备，并确定了其外消旋化能垒。此外，我们将1,1'-二薁-2,2'-二醇转化为相应的2,2'-双（膦酸酯），从而证明了通过交叉偶联实现官能团转化，并突出了多样化的潜力。
