Ring-opening formal hetero-[5+2] cycloaddition of 1-tosyl-2,3-dihydro-1H-pyrroles with terminal alkynes: entry to 1-tosyl-2,3-dihydro 2,3-dihydro-1H-azepines

Abstract

A new Lewis acid catalysed formal hetero-[5+2] cycloaddition of 2,3-dihydro-1H-pyrroles to terminal alkynes is described. By employing a FeCl₃ and BF₃·OEt₂ co-catalytic strategy, the ring-opening of 1-tosyl-2,3-dihydro-1H-pyrroles by selective cleavage of the C(sp²)–N bond and subsequent annulation have been achieved to access 1-tosyl-2,3-dihydro-1H-azepines with excellent regioselectivity, offering a new avenue for cycloaddition through the ring-opening of non-strained-ring-based units.