Iron-Catalyzed Fluoromethylene Transfer from a Sulfonium Reagent
Arturs Sperga1, Dzintars Zacs2, Janis Veliks1
1Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006 Riga, Latvia.
Abstract:
Herein, we report the first example of an iron porphyrin catalyzed fluoromethylene transfer from (2,4-dimethylphenyl)(fluoromethyl)(phenyl)sulfonium tetrafluoroborate to unactivated alkenes. The fluorocarbene or fluoromethylene synthon is the smallest "organic" node in a molecular graph of the organofluorine compounds. In this work, we present alternative solution to unavailable fluorodiazomethane (CHFN2), a missing one-carbon C1 piece in fluorine chemistry, by using a fluoromethylsulfonium reagent.
Related Concept Videos
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Preparation and Reactions of Sulfides
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Preparation and Reactions of Thiols
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Acid Halides to Alcohols: Grignard Reaction
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...


