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Iron-Promoted Difunctionalization of Alkenes by Phenyl­selenylation/1,2-Aryl Migration

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https://figshare.com/articles/dataset/Iron-Promoted_Difunctionalization_of_Alkenes_by_Phenyl_selenylation_1_2-Aryl_Migration/5433010
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Iron-promoted difunctionalization of α,α-diaryl and α-aryl-α-alkyl allylic alcohols has been efficiently achieved by means of N-(phenyl­seleno)­phthalimide (N-PSP) under mild conditions. An in situ generated phenylselenium cation (PhSe+) was added to the olefinic CC bond to initiate the regioselective phenylselenylation with concomitant 1,2-aryl migration, following a migration preference contrary to the well-known radical pathway. Hydrazonation of the resultant alkene difunctionalization products, that is, α-aryl-β-phenylselenyl ketones, and subsequent copper-catalyzed dehydroselenylation efficiently afforded functionalized 2-pyrazoline derivatives.
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2017-09-22
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