Eosin Y-catalyzed, visible-light-promoted carbophosphinylation of allylic alcohols via a radical neophyl rearrangement. Issue 13 (16th March 2018)

• Record Type: Journal Article
• Authors: Yin, Yao; Weng, Wei-Zhi; Sun, Jian-Guo; Zhang, Bo
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 13(2018)
• Page Start: 2356
• Page End: 2361
• Publication Date: 2018-03-16
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob00231b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An eosin Y-catalyzed, visible-light-promoted phosphinylation-induced 1, 2-rearrangement reaction of allylic alcohols to prepare various β-aryl-γ-ketophosphine oxides is presented. 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.