1. Radical-induced ring-opening and reconstruction of cyclobutanone oxime esters.
- Author
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Wang, Panpan, Zhao, Binlin, Yuan, Yu, and Shi, Zhuangzhi
- Subjects
- *
OXIMES , *COPPER catalysts , *SCISSION (Chemistry) , *ESTERS , *CYANIDES , *OXIDIZING agents - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2019
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