Oxidative Enantioselective α-Fluorination of Aliphatic Aldehydes Enabled by N-Heterocyclic Carbene Catalysis

Described is the first study on oxidative enantioselective α‐fluorination of simple aliphatic aldehydes enabled by N‐heterocyclic carbene catalysis. N‐fluorobis(phenyl)sulfonimide serves as a an oxidant and as an “F” source. The CF bond formation occurs directly at the α position of simple aliphati...

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Bibliographic Details
Published in:Angewandte Chemie 2015-01, Vol.127 (2), p.666-669
Main Authors: Li, Fangyi, Wu, Zijun, Wang, Jian
Format: Article
Language:English
Subjects:
Aldehyde
Aldehydes
Aliphatic compounds
Bonding
Carbenes
Catalysis
Enolate
Fluor
N-Heterocyclische Carbene
Oxidants
Oxidationen
Oxidizing agents
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Summary:Described is the first study on oxidative enantioselective α‐fluorination of simple aliphatic aldehydes enabled by N‐heterocyclic carbene catalysis. N‐fluorobis(phenyl)sulfonimide serves as a an oxidant and as an “F” source. The CF bond formation occurs directly at the α position of simple aliphatic aldehydes, thus overcoming nontrivial challenges, such as competitive difluorination and nonfluorination, and proceeds with high to excellent enantioselectivities. Eine Doppelrolle spielt NFSI in der Titelreaktion: Es wirkt als Oxidationsmittel und als „F“‐Quelle. Trotz konkurrierender Difluorierung kann eine C‐F‐Bindung direkt und hoch enantioselektiv in die α‐Stellung einfacher aliphatischer Aldehyde eingeführt werden.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201409473