Direct Synthesis of K-Region Functionalized Polycyclic Aromatic Hydrocarbons via Twofold Intramolecular C-H/C-H Arylation.

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. Our results also demonstrate the potential of these compounds as valuable candidates for the selective construction of larger PAH structures.