A Mechanistically Deceiving Formation of Aryl(1-indanyl)ketones via Acid-Catalyzed Cyclization of ortho-Alkynylarylmethanols.

Abstract

The generation of reactive carbocation intermediates from ortho-alkynylarylmethanol substrates was utilized as a means for the synthesis of aryl(1-indanyl)ketones . Substrates with a tertiary carbon at the β-position to the arene generated a carbocation intermediate via dehydration/protonation, followed by cyclization and hydration to give indanylketone products. For substrates with a quaternary carbon at that position, a carbocation intermediate was generated by protonation/elimination of water, followed by a 1,2-shift and a subsequent cyclization/hydration to give highly substituted indanylketones.