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. 2014 Oct 15;136(41):14401-4.
doi: 10.1021/ja508590k. Epub 2014 Oct 3.

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

Shaozhong Ge  1 , Sophie I Arlow, Michael G Mormino, John F Hartwig
Affiliations

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

Shaozhong Ge et al. J Am Chem Soc. .

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.

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Figures

Scheme 1
Scheme 1. Transformations of α-Aryl-α,α-difluoroacetamides
See this image and copyright information in PMC

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