Unknown

Dataset Information

0

Pd-catalyzed ?-arylation of trimethylsilyl enolates of ?,?-difluoroacetamides.

ABSTRACT: We report the arylation and heteroarylation of ?,?-difluoro-?-(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 ?-aryl-?,?-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 ?,?-difluoro carbonyl compounds, such as ?-aryl-?,?-difluoroketones, -acetaldehydes, -acetates, and acetic acids, and difluoroalkyl derivatives, such as 2-aryl-2,2-difluoroethanols and -ethylamines, under mild conditions.

SUBMITTER: Ge S 

PROVIDER: S-EPMC4210146 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Pd-catalyzed α-arylation of trimethylsilyl enolates of α,α-difluoroacetamides.

Ge Shaozhong S   Arlow Sophie I SI   Mormino Michael G MG   Hartwig John F JF  

Journal of the American Chemical Society 20141003 41

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 pla  ...[more]

Similar Datasets

Unknown Accounting for Strong Ligand Sensitivity in Pd-Catalyzed α-Arylation of Enolates from Ketones, Esters, and Nitroalkanes.
| S-EPMC7061083 | biostudies-literature
Unknown Palladium-catalyzed regiocontrolled alpha-arylation of trimethylsilyl enol ethers with aryl halides.
| S-EPMC2518395 | biostudies-literature
Unknown Palladium-catalyzed ?-arylation of zinc enolates of esters: reaction conditions and substrate scope.
| S-EPMC3800138 | biostudies-other
Unknown Direct Pd-catalyzed arylation of 1,2,3-triazoles.
| S-EPMC3689219 | biostudies-literature
Unknown Development of (trimethylsilyl)ethyl ester protected enolates and applications in palladium-catalyzed enantioselective allylic alkylation: intermolecular cross-coupling of functionalized electrophiles.
| S-EPMC4011571 | biostudies-literature
Unknown Computational Analysis of Enantioselective Pd-Catalyzed α-Arylation of Ketones.
| S-EPMC8009508 | biostudies-literature
Unknown Pd-Catalyzed Alkene Difunctionalization Reactions of Enolates for the Synthesis of Substituted Bicyclic Cyclopentanes.
| S-EPMC7886259 | biostudies-literature
Unknown Pd(II)-catalyzed para-selective C-H arylation of monosubstituted arenes.
| S-EPMC3345815 | biostudies-literature
Unknown Pd(II)-Catalyzed C3-Selective Arylation of Pyridine with (Hetero)arenes.
| S-EPMC4821414 | biostudies-literature
Unknown Pd(0)/PR3-catalyzed intermolecular arylation of sp3 C-H bonds.
| S-EPMC2727875 | biostudies-literature