ol9b02539_si_001.pdf (5.52 MB)
Visible-Light Photoredox-Catalyzed Decarboxylative Alkylation of Heteroarenes Using Carboxylic Acids with Hydrogen Release
journal contributionposted on 2019-08-21, 12:03 authored by Wan-Fa Tian, Chun-Hong Hu, Ke-Han He, Xiao-Ya He, Yang Li
Herein, we have developed visible-light photoredox-catalyzed decarboxylating carboxylic acids for alkylation of heteroarenes under mild conditions. The transformation occurred smoothly without the requirement of stoichiometric oxidants in the presence of 0.3 equiv of base, which benefited from the release of hydrogen (H2) and carbon dioxide (CO2). Various substrates and functional groups were tolerated. Primary mechanistic studies suggest that an oxidative quenching pathway and a reductive quenching pathway are both possible in the catalytic cycle.
requirementpresencecarbon dioxideHeteroarenePrimaryCarboxylic Acids0.3 equivheteroareneoxidative quenching pathwaystoichiometric oxidantsreductive quenching pathwayvisible-light photoredox-catalyzed decarboxylating carboxylic acidstransformationalkylationVisible-Light Photoredox-Catalyzed Decarboxylative AlkylationH 2Various substratesCO 2releaseHydrogen Release Herein