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

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.

SUBMITTER: Kyne RE

PROVIDER: S-EPMC2929327 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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

Kyne Robert E RE Ryan Michael C MC Kliman Laura T LT Morken James P JP

Organic letters 20100901 17

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. ...[more]

PMID: 20687578

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