Tunable synthesis of furfurylamines or β-amino alcohols via Ru-catalyzed N–H functionalization using biomass-derived polyols

Abstract

We report the highly efficient conversion of readily available biomass-derived polyols with amines to valuable furfurylamines or β-amino alcohols compounds using ruthenium catalysis. The reaction outcome is readily tuned by the simple addition of 4 ​Å molecular sieves (furfurylamines vs. β-amino alcohols) with high chemo-selectivity. The proposed reaction mechanism involves ruthenium-catalyzed hydrogen borrowing for the reduction of the imine intermediate and C–C bond cleavage of polyols via a retro-aldol process. A series of arylamines was successfully transformed into the desired products with moderate to good yields.

Keywords

• Polyols
• Furfurylamines
• β-Amino alcohols
• Ru-catalyzed