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

27 September 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

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.

Keywords

Visible Light
Decarboxylative Alkylations
Continuous Flow
redox-active ester

Supplementary materials

Title
Description
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Title
Visible Light-Induced Sulphide Anion-Catalysed Decarboxylative Alkylations in Batch and Continuous Flow
Description
The general information, preparation of substrates, experimental procedures, spectral data ,mechanistic studies, continious-flow system, and NMR Spectra were summerized in the supporting information
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