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Visible-light-induced consecutive C–C bond fragmentation and formation for the synthesis of elusive unsymmetric 1,8-dicarbonyl compounds

Author:
Ji, Meishan, Wu, Zhen, Zhu, Chen
Source:
Chemical communications 2019 v.55 no.16 pp. 2368-2371
ISSN:
1364-548X
Subject:
chemical bonding, chemical compounds, chemical reactions, irradiation, protocols
Abstract:
Synthesis of the valuable unsymmetric 1,8-dicarbonyl compounds remains underexplored currently. Herein, we disclose a new strategy for the synthesis of 1,8-diketones through the coupling of cyclopropanols and cyanohydrins under visible-light irradiation. The protocol features a cascade of intriguing ring opening of cyclopropanols and remote cyano migration. The unfavorable addition of an alkyl radical to an electron-rich alkene is facilitated by the intramolecular cyanohydrin interception. A variety of multiply functionalized 1,8-diketones are furnished in useful yields. The products could be further transformed into other valuable compounds, manifesting the utility of this method.
Agid:
6312732