Organic letters

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

VC Purohit, SP Allwein, RP Bakale

Index: Purohit, Vikram C.; Allwein, Shawn P.; Bakale, Roger P. Organic Letters, 2013 , vol. 15, # 7 p. 1650 - 1653

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Citation Number: 13

Abstract

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.