A simple, direct and facile hydroxylation of arylboronic acids has been described. The reaction is carried out under air, in an open flask, using 2 equivalents of sodium ascorbate. A variety of arylboronic acids can be transformed into the corresponding phenols in excellent to moderate isolated yields. The reaction tolerated the presence of functional groups, and molecules that are readily oxidized by H2O2can be present in the reaction mixture. This green methodology avoids the use of photoredox conditions, transition metals, or other strong oxidants.

A facile hydroxylation of arylboronic acids mediated by sodium ascorbate

Gualandi, Andrea;SAVOINI, ANDREA;Saporetti, Roberto;Franchi, Paola;Lucarini, Marco;Cozzi, Pier Giorgio
2018

Abstract

A simple, direct and facile hydroxylation of arylboronic acids has been described. The reaction is carried out under air, in an open flask, using 2 equivalents of sodium ascorbate. A variety of arylboronic acids can be transformed into the corresponding phenols in excellent to moderate isolated yields. The reaction tolerated the presence of functional groups, and molecules that are readily oxidized by H2O2can be present in the reaction mixture. This green methodology avoids the use of photoredox conditions, transition metals, or other strong oxidants.
ORGANIC CHEMISTRY FRONTIERS
Gualandi, Andrea*; Savoini, Andrea; Saporetti, Roberto; Franchi, Paola; Lucarini, Marco; Cozzi, Pier Giorgio
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/635166
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