An atom economical synthesis of 1H-isochromene, naphthoquinone, and isoquinoline derivatives has been developed. Using o-alkynylbenzyl alcohols, silyl enol ethers, and amines respectively, the gold(I)-catalyzed cyclization reactions proceed exclusively through a 6-endo-dig pathway due to the enhanced stability of the benzylic gold intermediates. The reactions work for a variety of electron poor and electron rich arenes and tolerate most common organic functional groups. Current work is underway to further investigate the mechanism of this reaction and expand its scope toward secondary and tertiary nucleophiles.

Gold(1)-catalyzed synthesis of 1H-isochromenes, naphthoquinones, and isoquinolines

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.