Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 49, Pages 20577-20582Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c10700
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Funding
- Emmy-Noether of the DFG [GU 1134/3]
- Heisenberg program of the DFG [GU 1134/4]
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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 alpha-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 noncovalent interactions. A wide variety of external nucleophiles are introduced with high regioselectivity applying this substrate-directing concept.
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