Unexpected results from the re-investigation of the Beckmann rearrangement of ketoximes into amides by using TsCl

TsCl (p-toluenesulfonyl chloride), a commercially available organosulfonyl chloride, has been widely used as a stoichiometric dehydrogenation reagent in the transformation of ketoximes into corresponding amides via the Beckmann rearrangement. It has been now found to catalyze the Beckmann rearrangement with high catalytic efficiency, converting a wide range of ketoximes into their corresponding amides under mild condition with good to excellent yields (up to 99% of yield with 1-5 mol% of catalyst loading). (C) 2009 Elsevier Ltd. All rights reserved.