Carbohydrate-based phosphines as supporting ligand for palladium-catalyzed Suzuki–Miyaura cross-coupling reaction

Abstract Carbohydrate-based mono-phosphines ( 1 and 2 ) derived from glucose have been explored as supporting ligand for palladium-catalyzed Suzuki–Miyaura reaction. The combination of phosphine to palladium in a ratio of 2:1 resulted in a longer-living system than that in a ratio of 1:1. Using K 2 CO 3 as base, aryl bromides as well as active aryl chlorides can be coupled nearly quantitatively by 0.1–0.2 mol % of 1 /Pd(OAc) 2 with 95–99% of isolated yields. The amount of the catalyst could be lowered to 0.01 mol % under the optimized condition with 80% yield at room temperature. The carbohydrate hydroxyl group in 1 was found to contribute to catalytic activity.