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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.


 

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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