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Mild and Rapid Aniline/HBF 4 •DEE‐Catalysed Formation of Sulfinyl Imines
Author(s) -
Blomkvist Björn,
Dinér Peter
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201901218
Subject(s) - aniline , imine , chemistry , dichloromethane , tetrafluoroborate , protonation , molecule , rhodium , medicinal chemistry , catalysis , polymer chemistry , photochemistry , organic chemistry , ion , solvent , ionic liquid
The 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.