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Green and Scalable Aldehyde‐Catalyzed Transition Metal‐Free Dehydrative N‐ Alkylation of Amides and Amines with Alcohols
Author(s) -
Xu Qing,
Li Qiang,
Zhu Xiaogang,
Chen Jianhui
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201200881
Subject(s) - chemistry , alkylation , aldehyde , dehydrogenation , catalysis , transition metal , alcohol , combinatorial chemistry , organic chemistry , alcohol oxidation
In contrast to the borrowing hydrogen‐type N‐ alkylation reactions, in which alcohols were activated by transition metal‐catalyzed anaerobic dehydrogenation, the addition of external aldehydes was accidentally found to be a simple and effective protocol for alcohol activation. This interesting finding subsequently led to an efficient and green, practical and scalable aldehyde‐catalyzed transition metal‐free dehydrative N‐ alkylation method for a variety of amides, amines, and alcohols. Mechanistic studies revealed that this reaction most possibly proceeds via a simple but interesting transition metal‐free relay race mechanism.