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Issue 24, 2020
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One-pot oxidative hydrolysis-oxidative cleavage of 7-borylindoles enables access to o-amidophenols and 4-acylbenzoxazoles

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Abstract

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.

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

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Article information


Submitted
18 Dec 2019
Accepted
20 Feb 2020
First published
20 Feb 2020

Chem. Commun., 2020,56, 3559-3562
Article type
Communication

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

K. Anderson, A. S. Eastabrook and J. Sperry, Chem. Commun., 2020, 56, 3559
DOI: 10.1039/C9CC09807K

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