Cascade Multicomponent Assemblies Involving 1,3-Enynes via Auto- Tandem Palladium Catalysis

Here we report a three-component auto-tandem reaction of 1,3-enyne-tethered carbonyls, organoboronic reagents, and suitable nucleophiles catalyzed by palladium, proceeding through consecutive intramolecular vinylogous addition, Suzuki coupling, and allylic alkylation. This process exhibited high chemo-and regioselectivity with 1,3,4-trifunctionalization of the 1,3enyne motif, and a wide range of 2H-chromenes, 1,2-dihydroquinolines, benzo[b]oxepines, 1,7-annulated indoles, and other frameworks were efficiently constructed in fair to good yields and E/Z selectivity.

Automated summary

This study reports a three-component auto-tandem reaction catalyzed by palladium, which efficiently constructs a variety of organic compounds. The reaction demonstrates high chemo- and regioselectivity, achieving 1,3,4-trifunctionalization of the 1,3-enyne motif.