title: Oxidative enantioselective α-fluorination of aliphatic aldehydes enabled by N-heterocyclic carbene catalysis.
abstract: 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.
authors.affiliation: Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, 100084 (China).
authors.forename: Fangyi
authors.initials: F
authors.lastname: Li
authors.forename: Zijun
authors.initials: Z
authors.lastname: Wu
authors.forename: Jian
authors.initials: J
authors.lastname: Wang
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D005461:Fluorine / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D006571:Heterocyclic Compounds; C030011:carbene; D005461:Fluorine; D008697:Methane
keywords: N-heterocyclic carbenes; aldehydes; enolates; fluorine; oxidation