N-Heterocyclic carbene-catalyzed SuFEx reactions of fluoroalkylated secondary benzylic alcohols
Zhihang Wei1, Fang Zhang1, Qichao Zhang1
1School of Chemistry and Chemical Engineering/State Key Laboratory Incubation Base for Green Processing of Chemical Engineering, Shihezi University, Shihezi 832003, P. R. China. helin@shzu.edu.cn.
Abstract:
An organocatalytic sulfur(VI)-fluoride exchange (SuFEx) reaction of secondary benzylic alcohols is reported. Under the catalysis of 10 mol% NHC, trifluoromethyl, difluoromethyl, bromodifluoromethyl, iododifluoromethyl, and pentafluoroethyl substituted secondary benzylic alcohols reacted with aryl sulfonyl fluorides or fluorosulfates to produce the corresponding sulfonates and sulfates in 62-99% yields. In these reactions, 4 Å molecular sieves were used as highly efficient HF scavengers, avoiding the use of stoichiometric amounts of silicon reagents and excess amounts of bases.
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