Pd(II)-Catalyzed Asymmetric Fluorination of α-Aryl-α-cyanophosphonates with the Aid of 2,6-Lutidine

Abstract

We describe herein the catalytic asymmetric fluorination of α-cyanophosphonates using chiral Pd(II)-bisphosphine complexes. While metal complexes failed to promote the reaction alone, a reaction system involving Pd(II) and organic base such as 2,6-lutidine was developed. The Pd(II) complex activates the substrates through coordination of the nitrile group, and 2,6-lutidine abstracts an acidic proton, thereby affording the desired fluorinated products in good yields with up to 78% ee. The products may be useful as novel physiological phosphate mimics in medicinal chemistry.