Base-promoted, CBr4-mediated tandem bromination/intramolecular Friedel–Crafts alkylation of N-aryl enamines: a facile access to 1H- and 3H-indoles

Abstract

Described here is a general and highly efficient method for the synthesis of 1H- and 3H-indoles. In the presence of CBr₄ and a suitable base, the cyclization of N-aryl enamines proceeds with high efficiency. Unlike previous intramolecular cross dehydrogenative coupling (CDC) of the same substrates, this process does not require the use of either a transition metal or a stoichiometric amount of oxidant. This method also features operational simplicity, easy scalability and good substrate tolerability. Control experiments indicate the reactions may proceed in a tandem sequence of bromination and intramolecular Friedel–Crafts alkylation in a simple one-pot procedure.