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A copper-catalyzed radical coupling/fragmentation reaction: efficient access to β-oxophosphine oxides

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Abstract

Described herein is a novel and efficient copper-catalyzed oxidative phosphonation of α-tert-hydroxylalkenes. This protocol displays a broad scope with good functional group compatibility and gives efficient access to diverse β-oxophosphine oxides from simple allylic alcohols and H-phosphine oxides. The mechanism is proposed to be an unprecedented three-component radical coupling/fragmentation cascade reaction of α-tert-hydroxylalkenes, HP(O)R1R2 and tert-butyl hydroperoxide (TBHP), in which the excess TBHP acts as not only a radical initiator but also a coupling partner.

Graphical abstract: A copper-catalyzed radical coupling/fragmentation reaction: efficient access to β-oxophosphine oxides

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Publication details

The article was received on 03 Jan 2019, accepted on 08 Feb 2019 and first published on 12 Feb 2019


Article type: Research Article
DOI: 10.1039/C9QO00006B
Citation: Org. Chem. Front., 2019, Advance Article

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    A copper-catalyzed radical coupling/fragmentation reaction: efficient access to β-oxophosphine oxides

    S. Feng, J. Li, F. He, T. Li, H. Li, X. Wang, X. Xie and X. She, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00006B

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