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Stepwise photosensitized C(sp3)–C(CO) bond cleavage and C–P bond formation of 1,3-dicarbonyls with arylphosphine oxides

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Abstract

A visible-light-induced metal-free cascade radical reaction of diarylphosphine oxides and 1,3-dicarbonyls was discovered to obtain β-ketophosphine oxides in moderate to excellent yields. On the basis of control experiments, cyclic voltammetry and Stern–Volmer quenching experiments, the target products were afforded via a cascade radical reaction of chemoselective C–C bond cleavage with a C–P bond formation. The active intermediates of PhCOO˙, β-dicarbonyl radical and P-radical were formed by the photosensitization process with single electron transfer (SET) or the free radical chain reaction with the decomposition of BPO under visible light irradiation. The obtained β-ketophosphine oxides could serve as good ligands to sensitize the Eu(III) metal centre.

Graphical abstract: Stepwise photosensitized C(sp3)–C(CO) bond cleavage and C–P bond formation of 1,3-dicarbonyls with arylphosphine oxides

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Publication details

The article was received on 17 Jan 2019, accepted on 07 Mar 2019 and first published on 08 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00075E
Citation: Org. Chem. Front., 2019, Advance Article

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    Stepwise photosensitized C(sp3)–C(CO) bond cleavage and C–P bond formation of 1,3-dicarbonyls with arylphosphine oxides

    X. Zhao, M. Huang, Y. Li, J. Zhang, J. K. Kim and Y. Wu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00075E

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