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Radical Addition of Arylboronic Acids to Various Olefins under Oxidative Conditions

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journal contribution
posted on 17.09.2010, 00:00 by Arne Dickschat, Armido Studer
Arylboronic acids are shown to be valuable precursors for aryl radicals upon treatment with manganese triacetate. Under these oxidative conditions the intermediately generated aryl radicals undergo addition to olefins to give the arylhydroxylation products A in the presence of dioxygen. In the absence of dioxygen, for some olefins double olefin addition and subsequent homolytic aromatic substitution provide tetrahydronaphthaline derivatives B in moderate to good yields.