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α-Functionalization of Ketones via a Nitrogen Directed Oxidative Umpolung
preprintsubmitted on 05.10.2020, 10:49 and posted on 06.10.2020, 04:47 by Gabriel M. Kiefl, Tanja Gulder
Reversing the polarity in molecules is a versatile tool for expanding the boundaries of structural space. Despite a manifold of different umpolung methods available today, overcoming the inherent reactivity still remains a constant challenge in organic chemistry. The oxidative α-functionalization of ketones by external nucleophiles constitute such an example. Herein, we present a hypervalent F-iodane mediated umpolung of pyridyl ketones triggered by Lewis base Lewis acid non-covalent interactions. A wide variety of external nucleophiles are introduced with high regioselectivity applying this substratedirecting concept.