Photoinduced Pd-Catalyzed 1,4-Dicarbofunctionalization of 1,3-Butadienes via Aliphatic C-H Bond Elaboration

Org Lett. 2025 Jan 7. doi: 10.1021/acs.orglett.4c04410. Online ahead of print.

Abstract

A three-component coupling strategy for 1,4-dicarbofunctionalization of 1,3-butadiene with C-H bearing substrates has been developed using photoinduced Pd catalysis, with aryl bromide serving as the hydrogen atom transfer (HAT) reagent. This photocatalytic coupling process achieves functionalized oxindole motifs in good yield and regioselectivity under mild reaction conditions. The versatility and synthetic utility of this method are demonstrated through the addition of a variety of C-H-bearing partners and various oxindole substrates to both substituted and unsubstituted butadiene.