One-pot oxidative hydrolysis-oxidative cleavage of 7-borylindoles enables access to o-amidophenols and 4-acylbenzoxazoles.

7-Borylindoles undergo a one-pot oxidative-hydrolysis of the arylboronate and oxidative cleavage of the indole C2-C3 double bond to afford o-amidophenol derivatives. Subsequent cyclisation delivers benzoxazoles bearing an acyl group at C4, a substitution pattern common to fungal-derived benzoxazole alkaloids. Using 7-borylindoles as substrates to access functionalised o-amidophenols circumvents the difficult preparation of these compounds from arenes, streamlining access to substituted 4-acylbenzoxazoles in the process.

A procedure for transforming indoles into indolequinones.

A procedure that converts a series of structurally diverse, readily available indole derivatives to their corresponding indolequinones is described. The three-step route commences with an iridium catalyzed C-H borylation to give a 7-borylindole that upon oxidation-hydrolysis affords the 7-hydroxyindole. Subsequent oxidation provides the indolequinone.