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Iron/Amino Acid Catalyzed Direct N‐Alkylation of Amines with Alcohols
Author(s) -
Zhao Yingsheng,
Foo Siong Wan,
Saito Susumu
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201006660
Subject(s) - alkylation , catalysis , alcohol , chemistry , carbon atom , organic chemistry , hydrogen atom , hydrogen , combinatorial chemistry , medicinal chemistry , group (periodic table) , alkyl
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 (S N ) at the sp 3 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.