Outline
DOI: 10.1021/acs.orglett.6c04139 ISSN: 1523-7060
Biocompatible C–S Bond Formation via Anion-Programmed Interfacial Proton Shuttle Catalysis
Ruiping Han, Rongjiao Qiao, Lei Zhang, Lei Wang, Fanyi Hou, Teck-Peng Loh, Peizhong XieAbstract
We developed an anion-programmed interfacial proton shuttle to catalyze C–S coupling between methyl 2-formylbenzoates and thiols in aqueous PBS buffer. Mechanistic experiments and DFT calculations reveal that kosmotropic anions organize interfacial water networks to facilitate proton transfer and drive the reaction. This protocol furnishes 3-thiophthalides with a broad substrate scope, permits site-selective peptide and protein modification, and may complement existing aqueous bioconjugation strategies.
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