Issue 35, 2024

The Chan–Lam-type synthesis of thioimidazolium salts for thiol–(hetero)arene conjugation

Abstract

The design of stable and variable aryl linkers for conjugating drug moieties to the metabolism-related thiols is of importance in drug discovery. We disclosed that thioimidazolium groups are unique scaffolds for the thiol–(hetero)arene conjugation under mild conditions. The drug bound thioimidazolium salts, which are easily accessible via a copper-mediated Chan–Lam process in gram-scale, could be successfully applied to the late-stage coupling of bioactive thiols to construct a broad array of drug-like molecules.

Graphical abstract: The Chan–Lam-type synthesis of thioimidazolium salts for thiol–(hetero)arene conjugation

Supplementary files

Article information

Article type
Communication
Submitted
12 Feb 2024
Accepted
29 Mar 2024
First published
01 Apr 2024

Chem. Commun., 2024,60, 4675-4678

The Chan–Lam-type synthesis of thioimidazolium salts for thiol–(hetero)arene conjugation

Y. Li, D. Han, Z. Luo, X. Lv and B. Liu, Chem. Commun., 2024, 60, 4675 DOI: 10.1039/D4CC00704B

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