title: Pd-catalyzed α-arylation of trimethylsilyl enolates of α,α-difluoroacetamides.
abstract: We report the arylation and heteroarylation of α,α-difluoro-α-(trimethylsilyl)acetamides with aryl and heteroaryl bromides catalyzed by an air- and moisture-stable palladacyclic complex containing P(t-Bu)2Cy as ligand. A broad range of electronically varied aryl and heteroaryl bromides underwent this transformation to afford α-aryl-α,α-difluoroacetamides in high yields. Due to the electrophilicity of the fluorinated amide, this palladium-catalyzed cross-coupling reaction provides a versatile platform to generate a range of α,α-difluoro carbonyl compounds, such as α-aryl-α,α-difluoroketones, -acetaldehydes, -acetates, and acetic acids, and difluoroalkyl derivatives, such as 2-aryl-2,2-difluoroethanols and -ethylamines, under mild conditions.
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720, United States.
authors.forename: Shaozhong
authors.initials: S
authors.lastname: Ge
authors.forename: Sophie I
authors.initials: SI
authors.lastname: Arlow
authors.forename: Michael G
authors.initials: MG
authors.lastname: Mormino
authors.forename: John F
authors.initials: JF
authors.lastname: Hartwig
mesh_terms: D002384:Catalysis; D005463:Fluoroacetates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D005463:Fluoroacetates; D014297:Trimethylsilyl Compounds; D010165:Palladium; C007741:fluoroacetamide