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

•Highly effective carbohydrate-based phosphine for Suzuki-Miyaura reaction.•Reaching room temperature activities with the conditions suitable for industrial application.•Observing a positive role of carbohydrate-hydroxy for catalytic reaction.

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 K2CO3 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.

Graphical abstractTwo easily accessing carbohydrate-based mono-phosphines show room temperature activities for palladium-catalyzed Suzuki-Miyaura reaction under the conditions suitable for pharmaceutical industrial application; the carbohydrate hydroxy participated in the catalytic reaction and contributed to the activity of the supported catalyst.Download full-size image