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

Author:
WangThese authors contributed equally., Panpan, Zhao, Binlin, Yuan, Yu, Shi, Zhuangzhi
Source:
Chemical communications 2019 v.55 no.13 pp. 1971-1974
ISSN:
1364-548X
Subject:
catalysts, chemical bonding, cleavage (chemistry), copper, cyanides, esters, ligands, oxidants, redox reactions, toxicity
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.
Agid:
6384927