title: Nucleophilic bromo- and iododifluoromethylation of aldehydes.
abstract: A method for bromo- and iododifluoromethylation of aldehydes using bromo- and iodo-substituted difluoromethyl silicon reagents (Me(3)SiCF(2)X) is described. The reaction is performed in the presence of a combination of tetrabutylammonium and lithium salts Bu(4)NX/LiX (X = Br or I) in propionitrile. It is believed that, in this process, a short-lived halodifluoromethyl carbanion serves as nucleophile, which is reversibly generated from difluorocarbene and a halide anion.
authors: N. D. Zelinsky Institute of Organic Chemistry, 119991 Moscow, Leninsky prosp. 47, Russian Federation.
authors: Mikhail D
authors: MD
authors: Kosobokov
authors: Vitalij V
authors: VV
authors: Levin
authors: Marina I
authors: MI
authors: Struchkova
authors: Alexander D
authors: AD
authors: Dilman
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000838:Anions; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D012821:Silanes / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000838:Anions; D006842:Hydrocarbons, Brominated; D006845:Hydrocarbons, Fluorinated; D006847:Hydrocarbons, Iodinated; D000644:Quaternary Ammonium Compounds; D012821:Silanes; C121084:difluorocarbene; D008094:Lithium; C009405:tetrabutylammonium