Issue 13, 2019
From the journal:

Chemical Communications

Radical-induced ring-opening and reconstruction of cyclobutanone oxime esters†

Panpan Wang,‡ab   Binlin Zhao,‡b   Yu Yuan*a  and  Zhuangzhi Shi ORCID logo *b  

* Corresponding authors

a College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China
E-mail: yyuan@yzu.edu.cn

b State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China
E-mail: shiz@nju.edu.cn

Abstract

The first example of intramolecular ring-opening and reconstruction of cyclobutanone oxime esters via selective C–C bond cleavage leading to the synthesis of 3,4-dihydronaphthalene-2-carbonitriles in the presence of a cheap copper catalyst has been reported. The protocol is distinguished by mild and safe reaction conditions that exclude ligands, oxidants, bases, toxic cyanide salts and tolerates a wide scope of cyclobutanones without compromising their efficiency and scalability. The alternative visible-light-driven photoredox process for this coupling reaction was also uncovered.

Graphical abstract: Radical-induced ring-opening and reconstruction of cyclobutanone oxime esters

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Article information

DOI
https://doi.org/10.1039/C8CC10109D
Article type
Communication
Submitted
21 Dec 2018
Accepted
14 Jan 2019
First published
14 Jan 2019

Chem. Commun., 2019,55, 1971-1974

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Radical-induced ring-opening and reconstruction of cyclobutanone oxime esters

P. Wang, B. Zhao, Y. Yuan and Z. Shi, Chem. Commun., 2019, 55, 1971 DOI: 10.1039/C8CC10109D

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