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.
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Zhao et al. (2011) studied this question.
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