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Updated: Apr 9, 2026

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C3- vs C10-Acylation of 9-Methoxyphenanthrene Controlled by Non-Covalent Interactions
Xunlan Yao1, Zhirui Wu1, Yatong Li1
1International Joint Research Laboratory of Nano-Micro Architecture Chemistry (NMAC), Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun 130012, P. R. China.
Abstract:
An approach to the regiodivergent acylation of the phenanthrene skeleton has been developed for the first time in the literature. C3- and C10-acylation products were obtained in good to high yields. DFT calculations revealed that the unique regioselectivity was controlled by Coulomb repulsion, π-π stacking, hydrogen bonding, and steric effects. The mechanism was further verified via the synthesis of naphthalene derivatives.
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