Functionalized polycyclic aromatic hydrocarbons (PAHs) are essential building blocks for the bottom-up fabrication of structurally uniform nanocarbons. Herein we report a simple and efficient synthetic method toward K-region hydroxy-functionalized PAHs via TEMPO-mediated twofold intramolecular C-H/C-H arylations of 1-biphenyl-2-yl-2-aryl-ethanone derivatives. This method achieves high yields and selectivity, synthesizing a variety of PAH frameworks, including pyrenes, chrysenes, benzo[]phenanthrenes, and benzo[]tetraphenes.
View Article and Find Full Text PDFThe properties of π-functional materials are predominantly influenced by both their molecular structures and interactions between π-systems. Recent advancements have focused on modifying the geometry or topology of π-molecules from planar to nonplanar conformations to tailor molecular properties. However, the interactions among nonplanar π-molecules remain largely unexplored, likely due to the significant reduction in contact surfaces arising from their curved structures.
View Article and Find Full Text PDFA highly efficient protocol for the synthesis of isoquinolinediones by Rh-catalyzed C-H activation/annulation/decarboxylation of N-tosylbenzamides with diazo compounds is reported. The switchable synthesis of isocoumarins was also achieved successfully via C-H activation/annulation with slight modification of the reaction conditions. Importantly, the synthetic utility of this new reaction was further demonstrated in an atom-economical and operationally convenient total synthesis of a TDP2 inhibitor derivative from commercially available starting materials.
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