543692-85-9Relevant academic research and scientific papers
An Unconventional Reaction of 2,2-Diazido Acylacetates with Amines
H?ring, Andreas P.,Biallas, Phillip,Kirsch, Stefan F.
supporting information, p. 1526 - 1539 (2017/04/01)
We have discovered that 2,2-diazido acylacetates, a class of compounds with essentially unknown reactivity, can be coupled to amines through a new strategy that does not involve any reagents. 2,2-Diazido acetate is the unconventional leaving group under carbon–carbon bond cleavage. This reaction leads to the construction of amide bonds, tolerates various functionalities and is performed equally well in numerous solvents under experimentally simple conditions. We also demonstrate that the isolation of the 2,2-diazido acylacetate compounds can be circumvented: Acylacetates were easily fragmented when treated with (Bu4N)N3 and iodine in the presence of an amine at room temperature. By using this method, a broad range of acylacetates with various structural motifs were directly transformed into amides.
Copper-Catalyzed Carbonylative Synthesis of Aliphatic Amides from Alkanes and Primary Amines via C(sp3)-H Bond Activation
Li, Yahui,Zhu, Fengxiang,Wang, Zechao,Wu, Xiao-Feng
, p. 5561 - 5564 (2016/08/18)
Amides are important intermediates and building blocks in organic synthesis. Among the known preparation procedures, aminocarbonylation is an interesting and powerful tool. However, most of the studies were focused on noble metal-catalyzed synthesis of ar
Catalytic hydrogenation of unactivated amides enabled by hydrogenation of catalyst precursor
Miura, Takashi,Held, Ingmar E.,Oishi, Shunsuke,Naruto, Masayuki,Saito, Susumu
, p. 2674 - 2678 (2013/06/26)
A general method for catalytic hydrogenation of unactivated amides was achieved. During the catalyst induction period, a novel structural change was observed involving full hydrogenation of the interior unsaturated bonds of the pyridines of the Ru-containing catalyst precursor. Based on this observation, the mechanism of amide hydrogenation may involve a two-step pathway, wherein the Ru catalyst having an H-Ru-N-H functionality is generated in the first step, followed by the amide carbonyl group interacting with the outer, rather than the inner, sphere of the Ru catalyst.
