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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… Click to show full 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.
Journal Title: Chemical communications
Year Published: 2019
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