A general and efficient method for the selective synthesis of beta-hydroxy sulfides and beta-hydroxy sulfoxides catalyzed by gallium(III) triflate.
Gallium(III) triflate-catalyzed ring opening of epoxides affords beta-hydroxy sulfides with high regioselectivity and chemoselectivity in high yields (84-97%) under solvent-free conditions. Additionally, a simple, efficient, and environmentally benign one-pot procedure for the synthesis of beta-hydroxy sulfoxides in sole water has been developed for the first time. The process, promoted by a H2O2-Ga(OTf)3 system, affords beta-hydroxy sulfoxides in high yields (81-94%) and high chemoselectivity without any detectable overoxidation to beta-hydroxy sulfones. The catalyst could be recovered easily after the reactions and reused without evident loss of activity.
Su
Weike
W
College of Pharmaceutical Sciences, Zhejiang Key Laboratory of Pharmaceutical Engineering, Zhejiang University of Technology, Hangzhou 310014, China. suweike@zjut.edu.cn
Chen
Jiuxi
J
Wu
Huayue
H
Jin
Can
C
D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry; D006860:Hydrogen Bonding; D008698:Mesylates / Q000737:chemistry*; D008958:Models, Molecular; D013440:Sulfides / Q000138:chemical synthesis*; D013454:Sulfoxides / Q000138:chemical synthesis*
D004852:Epoxy Compounds; D008698:Mesylates; D013440:Sulfides; D013454:Sulfoxides; C516572:gallium triflate