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

Org Biomol Chem

State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjia Xiang, Nanjing 210009, China.

Published: March 2018

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.

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Source
http://dx.doi.org/10.1039/C8OB00231BDOI Listing

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