Iron/Amino Acid Catalyzed Direct N-Alkylation of Amines with Alcohols

Ironing it out: The straightforward N‐alkylation using alcohols and iron/amino acid catalysis is described (see scheme). The reaction does not proceed by the conventional “borrowing hydrogen” mechanism, but appears to involve a substitution pathway (SN) at the sp3 carbon atom bearing the hydroxy gro...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2011-03, Vol.50 (13), p.3006-3009
Main Authors: Zhao, Yingsheng, Foo, Siong Wan, Saito, Susumu
Format: Article
Language:English
Subjects:
alcohols
Alcohols - chemistry
Alkylation
Amines - chemical synthesis
Amines - chemistry
amino acids
Amino Acids - chemistry
Catalysis
homogeneous catalysis
iron
Iron - chemistry
Molecular Structure
N-alkylation
Stereoisomerism
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Summary:Ironing it out: The straightforward N‐alkylation using alcohols and iron/amino acid catalysis is described (see scheme). The reaction does not proceed by the conventional “borrowing hydrogen” mechanism, but appears to involve a substitution pathway (SN) at the sp3 carbon atom bearing the hydroxy group of the alcohol. Developing a catalyst that is effective at a near neutral pH was key to the successful N‐alkylation.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201006660