Novel motif for bidentate P,N ligands. Application to Pd-catalyzed Suzuki cross-coupling reactions

A library of novel C2-symmetric P,N ligands based on a Tröger’s base backbone was prepared via a concise two-step synthesis starting from a commercially available aniline derivative. X-ray crystallography and 31P NMR studies confirm that a single ligand molecule can accommodate two palladium atoms via coordination to nitrogen and phosphorus. Preliminary results proved the synthetic potential of this species in Suzuki cross-coupling reactions of aryl bromides with arylboronic acids.

Graphical abstractNew P,N ligands based on Tröger’s base scaffold were synthesized. X-ray studies confirm their doubly bidentate character as one ligand molecule coordinates two palladium atoms resulting in C2-symmetric complex. The catalytic potential of the ligands was examined at palladium-catalyzed Suzuki cross-coupling reaction.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A library of novel P,N ligands based on Tröger’s base scaffold was synthesized. ► Their coordination properties were investigated by spectroscopic methods and X-ray analysis. ► Preliminary studies on their activity in Suzuki cross-coupling were done.