SuFEx Reactions of Sulfonyl Fluorides, Fluorosulfates, and Sulfamoyl Fluorides Catalyzed by N‑Heterocyclic Carbenes

Sulfur­(VI) fluoride exchange (SuFEx) click chemistry provides a powerful tool for the rapid assembly of modular connections. Herein, we report an organocatalytic SuFEx reaction of sulfonyl fluorides, fluorosulfates, and sulfamoyl fluorides. Under the catalysis of 10 mol % N-heterocyclic carbene (NH...

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Bibliographic Details
Published in:ACS catalysis 2023-11, Vol.13 (22), p.14503-14512
Main Authors: Lin, Muze, Luo, Jinyun, Xie, Yu, Du, Guangfen, Cai, Zhihua, Dai, Bin, He, Lin
Format: Article
Language:English
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Summary:Sulfur­(VI) fluoride exchange (SuFEx) click chemistry provides a powerful tool for the rapid assembly of modular connections. Herein, we report an organocatalytic SuFEx reaction of sulfonyl fluorides, fluorosulfates, and sulfamoyl fluorides. Under the catalysis of 10 mol % N-heterocyclic carbene (NHC), or under the relay catalysis of NHC and HOBt, different SuFExable hubs efficiently undergo click reactions with alcohols or amines to afford sulfonates, sulfonamides, sulfates, sulfamates, and sulfamides in 49–99% yields. More than 190 sulfonylated products, including 25 natural product derivatives, have been prepared through this method. Mechanism study showed that NHCs might act as a carbon-centered Broønsted base to activate alcohols or amines through the formation of hydrogen bonding.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.3c03820