Specific assembly of dihydrobenzofuran frameworks via Rh(iii)-catalysed C–H coupling of N-phenoxyacetamides with 2-alkenylphenols

Abstract

The Rh(III)-catalysed redox-neutral C–H coupling of N-phenoxyacetamides with 2-alkenylphenols has been developed, leading to the specific assembly of dihydrobenzofuran frameworks with good compatibility and profound synthetic utility. Integrated computational and experimental mechanistic studies revealed that the distinctive synergistic dual directing group-enabled unconventional reaction pathway involved a sequential intramolecular hydrogen transfer/nucleophilic 1,4-addition process in which a five-membered rhodacycle and the cyclohexa-2,4-dienone species might be used as the active intermediates.