Copper-Mediated Hydroxylation of Arenes and Heteroarenes Directed by a Removable Bidentate Auxiliary
Organic Letters2014Vol. 16(15), pp. 3904–3907
Citations Over TimeTop 1% of 2014 papers
Abstract
A copper-mediated C-H hydroxylation of arenes and heteroarenes using our newly developed PIP directing group has been developed. This procedure is scalable and compatible with a wide range of functional groups and heteroarenes, providing an operationally simple protocol for the synthesis of o-hydroxybenzamides. The hydroxylation of nicotinamides gave 4-oxo-1,4-dihydropyridine-3-carboxamides selectively. Preliminary mechanistic studies implicate that a basic ligand-enabled, irreversible, rate-determining CMD step is most likely involved in this process.
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