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

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
Further Information

Publication History

Publication Date:
18 November 2014 (online)



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.



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.