Allylation of nitrosobenzene with pinacol allylboronates. A regioselective complement to peroxide oxidation

RE Kyne, MC Ryan, LT Kliman, JP Morken

Index: Kyne, Robert E.; Ryan, Michael C.; Kliman, Laura T.; Morken, James P. Organic Letters, 2010 , vol. 12, # 17 p. 3796 - 3799

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Citation Number: 18

Abstract

Addition of nitrosobenzene to pinacol allylboronates leads to oxidation of the organoboron with concomitant rearrangement of the substrate alkene. This reaction appears to proceed by allylboration of the nitroso group in analogy to carbonyl and imine allylation reactions. Remarkably, the N− O bond is cleaved during the reaction such that simple alcohols are the final reaction product.