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Updated: Jun 1, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Photoinduced Difluoromethylation Cyclization to Generate Medium-Sized Difluoro-benzo[b]azepines
Dongyang Zhao1, Xin Wang1, Jiabo Huang2
1School of Pharmacy, Yantai University, Yantai 264005, P. R. China.
Abstract:
Compared with the energetically favorable 5- or 6-membered fluoro-functionalized heterocycles, the construction of medium-sized fluoro-heterocycles is relatively under-researched because of their inherently unfavorable enthalpic and entropic nature. Based on rational design and DFT calculations, a novel photocatalytic difluoromethyl radical-initiated intramolecular 7-endo-trig cyclization was realized, thus affording a sustainable route for the synthesis of challenging fluoro-functionalized medium-sized N-heterocycles. Depending on atomic dipole moment corrected Hirshfeld population (ADCH) charge calculations, the chemoselective 6-exo-trig radical cyclizations were further replenished. Large-scale synthesis and derivatization demonstrated the wide utility of this method.
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