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

作者：Muze Lin, Jinyun Luo, Yu Xie, Guangfen Du, Zhihua Cai, Bin Dai, Lin He · 发表于：ACS Catalysis · 年份：2023 · DOI：10.1021/acscatal.3c03820 · 被引用次数：47 · 研究领域：Sulfur-Based Synthesis Techniques、Click Chemistry and Applications、Fluorine in Organic Chemistry

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.