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Copper-catalyzed oxidative Heck reactions between alkyltrifluoroborates and vinyl arenes.

ABSTRACT: We report herein that potassium alkyltrifluoroborates can be utilized in oxidative Heck-type reactions with vinyl arenes. The reaction is catalyzed by a Cu(OTf)2/1,10-phenanthroline with MnO2 as the stoichiometric oxidant. In addition to the alkyl Heck, amination, esterification, and dimerization reactions of alkyltrifluoroborates are demonstrated under analogous reaction conditions. Evidence for an alkyl radical intermediate is presented.

SUBMITTER: Liwosz TW

PROVIDER: S-EPMC3978782 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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Copper-catalyzed oxidative Heck reactions between alkyltrifluoroborates and vinyl arenes.

Liwosz Timothy W TW Chemler Sherry R SR

Organic letters 20130604 12

We report herein that potassium alkyltrifluoroborates can be utilized in oxidative Heck-type reactions with vinyl arenes. The reaction is catalyzed by a Cu(OTf)2/1,10-phenanthroline with MnO2 as the stoichiometric oxidant. In addition to the alkyl Heck, amination, esterification, and dimerization reactions of alkyltrifluoroborates are demonstrated under analogous reaction conditions. Evidence for an alkyl radical intermediate is presented. ...[more]

PMID: 23734764

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