185669-66-3Relevant articles and documents
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.
Selective reductive amination of aldehydes from nitro compounds catalyzed by molybdenum sulfide clusters
Pedrajas,Sorribes,Junge,Beller,Llusar
supporting information, p. 3764 - 3768 (2017/08/21)
Secondary amines are selectively obtained from low value starting materials using hydrogen and a non-noble metal-based catalyst. The reductive amination of aldehydes from nitroarenes or nitroalkanes is efficiently catalyzed by a well-defined diamino molybdenum sulfide cluster in a one-pot homogeneous reaction. The integrity of the molecular cluster catalyst is preserved along the process.
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.
