Synthesis of naphthalene-substituted aromatic esters <i>via</i> Rh(<scp>iii</scp>)-catalyzed C–H bond naphthylation and cascade directing group transformation
Yue Cui, Siyu Li, Hesheng Wang, Jing Zeng, Yichen Wang, Xiubin Bu, Xiaobo Yang, Zhen Zhao
Abstract
A regioselective Rh(III)-catalyzed C-H bond naphthylation and cascade directing group (DG) transformation has been realized with aryl imidates and oxa bicyclic alkenes. Diverse naphthalene-substituted aromatic esters were synthesized fruitfully. The DG transformation into ester endows the strategy with chances of further C-H bond functionalization and derivatization. Preliminary mechanistic studies demonstrate that the ester carbonyl oxygen possibly originates from the corresponding oxa bicyclic alkene.
Topics & Concepts
ChemistryNaphthaleneCatalysisCascadeTransformation (genetics)Group (periodic table)Medicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryGeneChromatographyBiochemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAxial and Atropisomeric Chirality Synthesis