Direct hydroxyethylation of amines by carbohydrates via ruthenium catalysis

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....

Full description

Saved in:
Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2019, Vol.21 (11), p.3127-3132
Main Authors: Jia, Le, Makha, Mohamed, Du, Chen-Xia, Quan, Zheng-Jun, Wang, Xi-Cun, Li, Yuehui
Format: Article
Language:English
Subjects:
Alcohols
Alkylation
Amines
Carbohydrates
Catalysis
Chemical synthesis
Glycolaldehyde
Green chemistry
Organic compounds
Reagents
Ruthenium
Sugar
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1463-9262
1463-9270
DOI:10.1039/C9GC01195A