Issue 95, 2022
From the journal:

Chemical Communications

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

Yue Cui,a   Siyu Li,a   Hesheng Wang,a   Jing Zeng,a   Yichen Wang,a   Xiubin Bu,*a   Xiaobo Yang ORCID logo *ab  and  Zhen Zhao ORCID logo a  

* Corresponding authors

a Institute of Catalysis for Energy and Environment, College of Chemistry and Chemical Engineering, Shenyang Normal University, Shenyang, P. R. China
E-mail: bxy1223@gmail.com, yangxb@synu.edu.cn

b Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, P. R. China

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.

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

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Article information

DOI
https://doi.org/10.1039/D2CC05484A
Article type
Communication
Submitted
07 Oct 2022
Accepted
04 Nov 2022
First published
07 Nov 2022

Chem. Commun., 2022,58, 13230-13233

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

Y. Cui, S. Li, H. Wang, J. Zeng, Y. Wang, X. Bu, X. Yang and Z. Zhao, Chem. Commun., 2022, 58, 13230 DOI: 10.1039/D2CC05484A

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