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Synfacts 2014; 10(12): 1303
DOI: 10.1055/s-0034-1379422
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Catalytic gem-Difluoropropargylation Using Aryl and Alkenyl Boron Reagents

Contributor(s):
Paul Knochel
,
Thomas Klatt
Yu Y.-B, He G.-Z, Zhang X * Shanghai Institute of Organic Chemistry, P. R. of China
Synthesis of α,α-Difluoromethylene Alkynes by Palladium-Catalyzed gem-Difluoropropargylation of Aryl and Alkenyl Boron Reagents.

Angew. Chem. Int. Ed. 2014;
53: 10457-10461
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Publication History

Publication Date:
18 November 2014 (online)

 
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Key words

palladium - cross-coupling - boron reagents

Significance

The authors report the first palladium-catalyzed gem-difluoropropargylation of organoboron reagents using gem-difluoropropargyl bromides. A wide range of novel molecules with potential use as building blocks in organic synthesis were prepared. The reaction proceeds with high regioselectivity, broad substrate scope, and excellent functional group compatibility.


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Comment

Whereas in previous reports special phosphine ligands with large bite angles or very bulky substituents needed to be applied, now a simple ligand (o-Tol)3P can be used. The late-stage introduction of the fluoro substituents is suitable for applications in the synthesis of complex molecules.


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