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α-Functionalization of Ketones via a Nitrogen Directed Oxidative Umpolung

preprint
submitted on 05.10.2020 and posted on 06.10.2020 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.

Funding

Emmy-Noether program, GU 1134/3, DFG

Heisenberg program, GU 1134/4, DFG

History

Email Address of Submitting Author

tanja.gulder@uni-leipzig.de

Institution

Leipzig University

Country

Germany

ORCID For Submitting Author

0000-0003-4870-2266

Declaration of Conflict of Interest

The authors declare no conflict of interest

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