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Direct Alkylation of Amines with Alcohols Catalyzed by Base

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journal contribution
posted on 06.11.2015, 00:00 by Qiang-Qiang Li, Zu-Feng Xiao, Chuan-Zhi Yao, Hong-Xing Zheng, Yan-Biao Kang
A base-catalyzed/promoted transition-metal-free direct alkylation of amines with alcohols has been developed, giving the desired amines in generally high yields from either aromatic or aliphatic alcohols. On the basis of the 1H NMR and in situ IR (React-IR) monitoring experiments, isotope-labeling experiments, as well as control experiments, a novel “hemiaminal” model is proposed to understand the mechanism, which explains the formation of the “extra” aldehyde in the reaction.