Construction of hexabenzocoronene-based chiral nanographenes

• Ranran Li,
• Di Wang,
• Shengtao Li and
• Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

• this helical aza-NG was achieved by introducing a chiral auxiliary reagent at the nitrogen site [40], and the racemization barrier of one enantiomer was measured as 26.2 kcal/mol by monitoring the changes of CD spectra at 60–80 °C. The synthesis started with the Diels−Alder reaction of 5H-dibenzo[b,f

• ]azepine and tetrabromothiophene-S,S-dioxide, followed by oxidative aromatization in the presence DDQ to afford compound 25 in an overall 75% yield. Suzuki−Miyaura cross-coupling reaction of compound 25 with (4-ethylphenyl)boronic acid in the presence of Pd(CH3CN)2Cl2, SPhos, and K3PO4 then furnished the

Strategies in the synthesis of dibenzo[b,f]heteropines

• David I. H. Maier,
• Barend C. B. Bezuidenhoudt and
• Charlene Marais

Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51

• David I. H. Maier Barend C. B. Bezuidenhoudt Charlene Marais Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9300, South Africa 10.3762/bjoc.19.51 Abstract The dibenzo[b,f]azepine skeleton is important in the pharmaceutical industry, not only in terms of existing

• commercial antidepressants, anxiolytics and anticonvulsants, but also in reengineering for other applications. More recently, the potential of the dibenzo[b,f]azepine moiety in organic light emitting diodes and dye-sensitized solar cell dyes has been recognised, while catalysts and molecular organic

• frameworks with dibenzo[b,f]azepine derived ligands have also been reported. This review provides a brief overview of the different synthetic strategies to dibenzo[b,f]azepines and other dibenzo[b,f]heteropines. Keywords: dibenzo[b,f]azepine; dibenzo[b,f]heteropine; dibenzo[b,f]oxepine; iminostilbene