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… Click to show full 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.
               
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