Bis(1-adamantyl)(2-morpholinophenyl)phosphine (Mor-DalPhos)

Abstract

(ligand employed in transition metal-catalyzed reactions) Alternate Name: di(1-adamantyl)-2-morpholinophenylphosphine. Physical Data: mp 219–224 °C. Solubility: soluble in most polar organic solvents. Form Supplied in: White to pale yellow powder or crystals. Also commercially available as preformed Au-ligand complexes such as (MeCN)(Mor-Dalphos)Au(I) SbF_6 and [Mor-Dalphos]Au(I)Cl. Analysis of Reagent Purity: NMR, Elemental Analysis. Preparative Method: Pd-catalyzed cross-coupling of N-(2-bromophenyl)morpholine and diadamantyl phosphine. Handling, Storage, and Precautions: the phosphine is not particularly sensitive to air or moisture although precautions, such as storage under inert atmosphere in a cool place, should be taken during long-term storage. Bis(1-adamantyl)(2-morpholinophenyl)phosphine (Mor-DalPhos) is a phosphine ligand that has been employed in Pd-catalyzed cross-coupling reactions and Au-catalyzed hydroamination and [3+2] annulations. This ligand, when combined with an appropriate Pd-source, is particularly effective for promoting selective monoarylation processes between aryl electrophiles and nucleophiles such as ammonia, hydrazine, and acetone.