American Chemical Society
ol400432x_si_001.pdf (1.96 MB)

Catalytic Oxidative 1,2-Shift in 1,1′-Disubstituted Olefins Using Arene(iodo)sulfonic Acid as the Precatalyst and Oxone as the Oxidant

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journal contribution
posted on 2013-04-05, 00:00 authored by Vikram C. Purohit, Shawn P. Allwein, Roger P. Bakale
An efficient, catalytic hypervalent iodine-mediated oxidative 1,2-shift of 1,1′-disubstituted olefins is described. This methodology provides concise access to homobenzylic ketones with electron-donating substituents. In the case of cyclic systems, this transformation results in ring-expanded β-benzocycloalkanones, which are useful for further elaboration.