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

2011; Wiley; Volume: 50; Issue: 13 Linguagem: Inglês

10.1002/anie.201006660

1521-3773

Yingsheng Zhao, Siong Wan Foo, Susumu Saito,

Chemical Synthesis and Analysis

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. Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.