Air-stable and highly efficient indenyl-derived phosphine ligand: Application to Buchwald–Hartwig amination reactions

2-Mesitylindenyl phosphine ligand (1) and [(2-mesitylindenyl)dicyclohexyl-phosphine]PdCl2 (2) have been synthesized and fully characterized by NMR and elemental analysis, as well as by X-ray crystallography for 2. A Highly active catalyst system derived from a palladium precatalyst and bulky 2-mesitylindenyl phosphine ligand (1) for the Buchwald–Hartwig amination reaction of aryl halides with primary and secondary amines has been developed. This method allows for the preparation of a wide variety of amines in moderate to excellent yields and displays a high level of activity for the coupling of aryl chlorides as well as hindered aryl bromides.

2-Mesitylindenyl phosphine ligand and [(2-mesitylindenyl)dicyclohexyl phosphine]-PdCl2 have been synthesized, and utilized in the palladium-catalyzed Buchwald–Hartwig amination reaction, providing good to excellent yields of amination products. Figure optionsDownload as PowerPoint slideHighlights
► 2-Mesitylindenyl phosphine ligand (1) has been synthesized.
► [(2-Mesitylindenyl)dicyclohexyl-phosphine]PdCl2 (2) has been synthesized.
► A highly active catalyst system for the C–N coupling reaction has been developed.