N-Alkyl indoles can be oxidativelycoupled with arenes such as benzene in an acidic medium. PivOH was used as theacidic additive because it minimized the formation of acetoxylated by-productsThe use of AgOAc as stoichiometric oxidant produces selective arylation atindole's 2-position. Presence of electron withdrawing group on the indolesubstrate enhances the selectivity of arylation at indole's 2-position. SEM(2-(trimethylsilyl)ethoxy-methyl) represents a versatile and robust protectinggroup for indoles that can readily be removed under a variety of reactionconditions. Herein, we disclose a catalytic system that allowed the efficientarylation of  N-acetylindoles and N-alkylindoleswhich leads a diverse library of 2-arylindoles.

Oxidant-controlled regioselectivity in the oxidative arylation of 
<i>N</i>-acetylindoles and <i>N</i>-alkylindoles

240th National Meeting (2010)

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Oxidant-controlled regioselectivity in the oxidative arylation of N-acetylindoles and N-alkylindoles