Synthesis of naphthalene-substituted aromatic esters via Rh(iii)-catalyzed C-H bond naphthylation and cascade directing group transformation

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.

Automated summary

In this study, a regioselective Rh(III)-catalyzed strategy was developed for C-H bond naphthylation using aryl imidates and oxa bicyclic alkenes, resulting in the synthesis of diverse naphthalene-substituted aromatic esters. The possibility of further functionalization and derivatization of C-H bonds is achieved through the cascade directing group transformation into ester.