Jiao chlorination
Jiao chlorination is a DMSO-catalyzed chlorination reaction that uses N-chlorosuccinimide (NCS) as the chlorinating reagent.[1] It was reported by the group of Ning Jiao at Peking University in 2020.[2] The reaction enables the C–H chlorination of arenes and heteroarenes, including the late-stage modification of drugs, natural products, peptides, and functional molecules.
Mechanism
In this reaction, DMSO acts as a Lewis-base catalyst rather than as a stoichiometric oxidant. The oxygen atom of DMSO interacts with the electrophilic chlorine derived from NCS to generate an activated chlorinating species, commonly represented as [DMSO-Cl]+ which has been determined by high-resolution mass spectrometry. Computational studies indicated that this species is more reactive toward aromatic π systems than NCS. When DMSO is present in excess, a second DMSO molecule can coordinate to [DMSO-Cl]+ to form a less reactive [(DMSO)2-Cl]+ adduct, which decreases the chlorination rate.[2]
References
- ↑ He, Li-Bowen; Liu, Heng; Chen, Qing-An (2026). "DMSO: A Magic Chemical for Bromination and Chlorination". Chinese Journal of Chemistry. 44 (15): 2593–2605. doi:10.1002/cjoc.70623. ISSN 1614-7065.
- ↑ 2.0 2.1 Song, Song; Li, Xinyao; Wei, Jialiang; Wang, Weijin; Zhang, Yiqun; Ai, Lingsheng; Zhu, Yuchao; Shi, Xiaomeng; Zhang, Xiaohui; Jiao, Ning (February 2020). "DMSO-catalysed late-stage chlorination of (hetero)arenes". Nature Catalysis. 3 (2): 107–115. doi:10.1038/s41929-019-0398-0. ISSN 2520-1158.
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