657408-07-6

Uses

SPhos [2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl] is an air-stable, electron-rich biaryl phosphine ligand.

Reactions

Ligand/palladium catalyst for general Suzuki-Miyaura cross-coupling reactions. Ligand/palladium catalyst for the Suzuki-Miyaura coupling of aryltrifluoroborates with aryl chlorides. Ligand/palladium catalyst for the Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters. Ligand/palladium catalyst for the Kumada-Corriu cross-coupling reaction. Ligand/palladium catalyst for the borylation of aryl halides with pinacol borane. Suzuki couplings involving amino acids. Synthesis of biaryl derivatives of 4-hydroxyphenyl glycine, tyrosine and tryptophan. Synthesis of substituted adamantylzinc reagents using Mg-insertion in the presence of zinc chloride. Highly efficient catalyst for the palladium-catalyzed Suzuki-Miyura reaction of heteroaryl halides and heteroaryl boronic acids and esters.

Chemical Properties

White solid

General Description

SPhos [2-Dicyclohexylphosphino-2′, 6′-dimethoxybiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions. S-Phos can be prepared in one pot by the directed ortho-lithiation of 1,3-dimethoxybenzene with n-BuLi at room temperature, followed by cooling to 0 °C and addition of neat 1-bromo-2-chlorobenzene to give 2-bromo-1′,3′-dimethoxybiphenyl. Without isolation, the THF solution is cooled to −78°C and treated sequentially with n-BuLi and Cy2PCl, followed by warming to room temperature. After workup and crystallization, S-Phos is obtained in 59% yield.