Mild and Rapid Aniline/HBF4 center dot DEE-Catalysed Formation of Sulfinyl Imines

摘要

abstract_textpThe combination of anline and tetrafluoroboric acid diethyl etherate (2.5 mol and 5 mol, respectively) significantly accelerates the formation of sulfinyl imines in dichloromethane and isopropylacetate at room temperature compared to previous procedures. A DFT and NMR spectroscopic study shows that the anilinium tetrafluoroborate complex is solvated by sulfinamide molecules in the initial state and that the rate-limiting step of the reaction is the addition of the sulfinamide molecule to the protonated aniline-based imine. In addition, the catalytic system was also utilised in a one-pot, two step reaction, where the in situ formed sulfinyl imine was arylated in a rhodium catalysed reaction with high diastereoselectivity./p/abstract_text