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Direct hydroxyethylation of amines by carbohydrates via ruthenium catalysis

Author:
Jia, Le, Makha, Mohamed, Du, Chen-Xia, Quan, Zheng-Jun, Wang, Xi-Cun, Li, Yuehui
Source:
Green chemistry 2019 v.21 no.11 pp. 3127-3132
ISSN:
1463-9270
Subject:
amino alcohols, aromatic amines, catalysts, catalytic activity, green chemistry, hydrogen, imines, ruthenium, sugars
Abstract:
An efficient and halogen-free catalytic methodology for the synthesis of β-amino alcohols from aromatic amines and biomass-derived carbohydrates is demonstrated for the first time. The activation of C5/C6 sugars by a ruthenium catalyst selectively generates the C2 alkylating reagent glycolaldehyde. The transformation involves metal-catalyzed hydrogen borrowing for the reduction of the imine intermediate. A series of arylamines bearing various substituents were successfully transformed into the desired products in good to excellent yields.
Agid:
6460468