Biocompatible C–S Bond Formation via Anion-Programmed Interfacial Proton Shuttle Catalysis
Abstract 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.
Authors
- Fanyi Hou
- Teck‐Peng Loh (ORCID: https://orcid.org/0000-0002-2936-337X)
- Ruiping Han
- Lei Zhang (ORCID: https://orcid.org/0000-0003-0100-8357)
- Peizhong Xie (ORCID: https://orcid.org/0000-0002-6777-0443)
- Lei Wang
- Rongjiao Qiao
Institutions
- Nanjing Tech University (CN)
- Tianjin Chengjian University (CN)
- Nanyang Technological University (SG)
- Henan University of Technology (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-10-27
- DOI
- https://doi.org/10.1021/acs.orglett.6c04139
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- Agency for Science, Technology and Research
- Nanyang Technological University
- National Natural Science Foundation of China
- Natural Science Foundation of Jiangsu Province
- Six Talent Peaks Project in Jiangsu Province