Rapid access to 3-acyl indoles using ethyl acetate/triflic acid couple as the acylium donor and Cu(OAc)2 catalysed aerial oxidation of indole benzoins

Abstract

Esters are potential acyl donors but are relatively unexplored for that purpose. A facile installation of acyl groups at the C-3 position of indoles under triflic acid catalysed conditions with easily available and cheap esters as new acylating agents is described herein. Furthermore, heterocycles like N-protected pyrrole, furan and thiophene were also suitable substrates for similar C-2 acylation. Analogous C-3 benzoylated products of indole were obtained, albeit in lower yields, by using methyl benzoate as a benzoyl donor. The benzoylated products were synthesised in much better yields via a copper(II) catalysed aerial oxidation of indole containing benzoins.