Acid-Enabled Palladium-Catalyzed β-C(sp3)-H Functionalization of Weinreb Amides

Pd-catalyzed modification of C-H bonds via chelation with weakly coordinating groups normally requires a transient directing group or presynthesized nitrogen-based strong coordinating ligands. Herein, we report Pd(II)-catalyzed C(sp(3))-H arylation and alkenylation of Weinreb amides. A commercially available, inexpensive sulfonic acid was employed to enhance the coordination of the catalyst with weak-coordinating substrates by increasing the electrophilicity of in situ formed palladium catalysts.

Automated summary

In this study, a new method was developed to enhance the coordination of Pd catalysts with weak-coordinating substrates using a commercially available sulfonic acid, enabling arylation and alkenylation of C(sp(3))-H bonds of Weinreb amides.