Cu-catalyzed arylation of S-tosyl peptides with arylboronic acids

Abstract

Transition metal-mediated S-arylation has emerged as a powerful tool for the synthesis of S-arylcysteine and S-arylpeptide, which are useful building blocks in pharmacophores and biomolecules. In contrast, the catalytic protocols for arylation remain unexplored, particularly methods employing abundant metal catalysts (e.g. Cu and Ni). Herein, we reported the copper-catalyzed arylation chemistry of S-tosyl peptides with readily available arylboronic acids. This method features excellent yields and a wide variety of aryl groups, enabling the efficient synthesis of S-arylated cysteines and peptides under mild reaction conditions (room temperature, weak base). The reaction can be carried out in both batch and flow, demonstrating its utility in organic synthesis.