Visible Light-Induced Sulphide Anion-Catalysed Decarboxylative Alkylations in Batch and Continuous Flow

We demonstrated herein a versatile protocol for visible-light-induced sulphide anion-catalysed decarboxylative cross-couplings. An array of primary, secondary, tertiary and amino acid-derived redox-active esters (RAEs) were all amenable substrates to undergo radical decarboxylation to be coupled with a diverse range of nucleophiles, creating challenging C(sp3)-C(sp3) and C(sp3)-C(sp2) bonds with high efficiency. We note that Katritzky’s salt and Togni’s reagent were also suitable substrates, affording deaminative alkylation and trifluoromethylation products in high yields. Density functional theory calculations and mechanism experiments indicate that a charge-transfer complex was formed between sulphide anions and RAEs in the amide solvent. Additionally, a one-pot two-step telescoped procedure and continuous-flow process further increase the synthetic utility of this catalytic system.