Issue 29, 2015
From the journal:

Organic & Biomolecular Chemistry

A facile and regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion†

Jiajia Yu,a   Huijun Zhao,a   Shuguang Liang,a   Xiaoguang Bao*b  and  Chen Zhu*ac  

* Corresponding authors

a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, People's Republic of China
E-mail: chzhu@suda.edu.cn

b College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu 215123, People's Republic of China
E-mail: xgbao@suda.edu.cn

c Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People's Republic of China

Abstract

A regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion is described. A variety of 1-tetralones are furnished under mild reaction conditions from tertiary cyclobutanols regardless of the electronic properties and steric hindrance of substituents, providing a new and practical method to access diverse 1-tetralone building blocks. Preliminary experimental and DFT studies revealed that a radical-mediated sequence of C–C bond cleavage/C–C bond formation is involved.

Graphical abstract: A facile and regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion

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Article information

DOI
https://doi.org/10.1039/C5OB01222H
Article type
Communication
Submitted
16 Jun 2015
Accepted
25 Jun 2015
First published
25 Jun 2015

Org. Biomol. Chem., 2015,13, 7924-7927

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A facile and regioselective synthesis of 1-tetralones via silver-catalyzed ring expansion

J. Yu, H. Zhao, S. Liang, X. Bao and C. Zhu, Org. Biomol. Chem., 2015, 13, 7924 DOI: 10.1039/C5OB01222H

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