Cis-Selective Decarboxylative Alkenylation of Aliphatic Carboxylic Acids with Vinyl Arenes Enabled by Photoredox/Palladium/Uphill Triple Catalysis

Org Lett. 2018 May 4;20(9):2559-2563. doi: 10.1021/acs.orglett.8b00712. Epub 2018 Apr 17.

Abstract

An iridium photoredox catalyst in combination with phenanthroline-supported palladium catalyst catalyzes decarboxylative alkenylation of tertiary and secondary aliphatic carboxylic acids with vinyl arenes to deliver β-alkylated styrenes with Z-selectivity. A broad scope of aliphatic carboxylic acids, including amino acids, exhibit as amenable substrates, and external oxidant is not required. The reaction proceeds by synergistic utilization of both energy-transfer and electron-transfer reactivity of iridium photoredox catalyst merging with palladium-catalyzed hydride elimination and insertion.

Publication types

  • Research Support, Non-U.S. Gov't