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Issue 13, 2018
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Eosin Y-catalyzed, visible-light-promoted carbophosphinylation of allylic alcohols via a radical neophyl rearrangement

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Abstract

A visible-light-promoted phosphinylation of allylic alcohols with concomitant 1,2-aryl migration is described. This transformation proceeds smoothly under metal-free and mild conditions by using an inexpensive organic dye, eosin Y, as the photocatalyst, affording various β-aryl-γ-ketophosphine oxides in moderate to good yields. Mechanistic studies suggested that the 1,2-aryl migration proceeded through a radical (neophyl) rearrangement.

Graphical abstract: Eosin Y-catalyzed, visible-light-promoted carbophosphinylation of allylic alcohols via a radical neophyl rearrangement

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Publication details

The article was received on 27 Jan 2018, accepted on 09 Mar 2018 and first published on 10 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00231B
Citation: Org. Biomol. Chem., 2018,16, 2356-2361
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    Eosin Y-catalyzed, visible-light-promoted carbophosphinylation of allylic alcohols via a radical neophyl rearrangement

    Y. Yin, W. Weng, J. Sun and B. Zhang, Org. Biomol. Chem., 2018, 16, 2356
    DOI: 10.1039/C8OB00231B

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