200279-80-7Relevant academic research and scientific papers
Enhanced Hydride Donation Achieved Molybdenum Catalyzed Direct N-Alkylation of Anilines or Nitroarenes with Alcohols: From Computational Design to Experiment
Huang, Ming,Huang, Yong-Liang,Ke, Zhuofeng,Lan, Xiao-Bing,Li, Weikang,Liu, Jiahao,Liu, Yan,Ye, Zongren,Zhao, Cunyuan
, p. 10377 - 10382 (2021)
An example of homogeneous Mo-catalyzed direct N-alkylation of anilines or nitroarenes with alcohols is presented. The DFT aimed design suggested the easily accessible bis-NHC-Mo(0) complex features a strong hydride-donating ability, achieving effective N-alkylation of anilines or challenging nitroarenes with alcohols. The enhanced hydride-donating strategy should be useful in designing highly active systems for borrowing hydrogen transformations.
Base-mediated cascade amidination/: N -alkylation of amines by alcohols
Hu, Mao-Lin,Jia, Xiaofei,Liang, Zuyu,Lu, Fenghong,Zhang, Chunyan,Zhang, Guoying
supporting information, p. 10489 - 10492 (2020/10/02)
A base-mediated cascade amidination/N-alkylation reaction of amines by alcohols has been developed. For the first time, nitriles have been identified as an efficient and benign water acceptor reagent in N-alkylation. Notably, the procedure tolerates a series of functional groups, such as methoxyl, halo, vinyl and hetero groups, providing a convenient method to construct different substituted diamino compounds, 15N labeled amine and could be scaled up to 1 mol scale offering 138.7 g of the desired product in good yield in one-pot. Mechanistic studies provided strong evidence for the amidination of amines with nitriles facilitated by t-BuOK.
Cobalt-Catalyzed Alkylation of Aromatic Amines by Alcohols
R?sler, Sina,Ertl, Michael,Irrgang, Torsten,Kempe, Rhett
supporting information, p. 15046 - 15050 (2016/01/25)
The implementation of inexpensive, Earth-abundant metals in typical noble-metal-mediated chemistry is a major goal in homogeneous catalysis. A sustainable or green reaction that has received a lot of attention in recent years and is preferentially catalyzed by Ir or Ru complexes is the alkylation of amines by alcohols. It is based on the borrowing hydrogen or hydrogen autotransfer concept. Herein, we report on the Co-catalyzed alkylation of aromatic amines by alcohols. The reaction proceeds under mild conditions, and selectively generates monoalkylated amines. The observed selectivity allows the synthesis of unsymmetrically substituted diamines. A novel Co complex stabilized by a PN5P ligand catalyzes the reactions most efficiently. Sustainable C-N bond formation: An easily accessible Co complex efficiently catalyzes the alkylation of aromatic amines by alcohols. The mild reaction conditions permit the use of sensitive functional groups (I, Br) and the observed selective monoalkylation allows the synthesis of unsymmetrically alkylated diamines.
Green and scalable aldehyde-catalyzed transition metal-free dehydrative N-alkylation of amides and amines with alcohols
Xu, Qing,Li, Qiang,Zhu, Xiaogang,Chen, Jianhui
supporting information, p. 73 - 80 (2013/03/13)
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. Copyright
