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submitted on 18.08.2020 and posted on 19.08.2020by Revannath L. Sutar, Nikita Erochok, Stefan Huber
A series of cationic monodentate and bidentate
iodo(benz)imidazolium-based halogen bond (XB) donors were employed as
catalysts in a Mukaiyama aldol reaction. While 5 mol% of a monodentate variant
showed noticeable activity, a syn-preorganized
bidentate XB donor provided a strong performance even with 0.5 mol% loading. In
contrast to the very active BArF4 salts, PF6
or OTf salts were either inactive or showed background reaction. Repetition
experiments clearly ruled out a potential hidden catalysis by elemental iodine
and demonstrated the stability of our catalyst over three consecutive cycles.