85995-47-7Relevant academic research and scientific papers
C-N and N-H Bond Metathesis Reactions Mediated by Carbon Dioxide
Wang, Yehong,Zhang, Jian,Liu, Jing,Zhang, Chaofeng,Zhang, Zhixin,Xu, Jie,Xu, Shutao,Wang, Fangjun,Wang, Feng
, p. 2066 - 2072 (2015)
Herein, we report CO2-mediated metathesis reactions between amines and DMF to synthesize formamides. More than 20 amines, including primary, secondary, aromatic, and heterocyclic amines, diamines, and amino acids, are converted to the corresponding formamides with good-to-excellent conversions and selectivities under mild conditions. This strategy employs CO2 as a mediator to activate the amine under metal-free conditions. The experimental data and in situ NMR and attenuated total reflectance IR spectroscopy measurements support the formation of the N-carbamic acid as an intermediate through the weak acid-base interaction between CO2 and the amine. The metathesis reaction is driven by the formation of a stable carbamate, and a reaction mechanism is proposed.
Transformylating amine with DMF to formamide over CeO2 catalyst
Wang, Yehong,Wang, Feng,Zhang, Chaofeng,Zhang, Jian,Li, Mingrun,Xu, Jie
, p. 2438 - 2441 (2014/03/21)
We here report a new protocol for the formylation of various amines, primary or secondary, aromatic or alkyl, cyclic or linear, mono- or di-amine, with dimethylformamide (DMF) as the formylation reagent to obtain the corresponding formamides in good to excellent yields over CeO2 catalyst. The reaction requires no homogeneous acidic or basic additives and is tolerant to water.
Synthesis of 2-oxazolones and α-aminoketones via palladium-catalyzed reaction of β,β-dibromoenamides
Chai, David I.,Hoffmeister, Laura,Lautens, Mark
supporting information; experimental part, p. 106 - 109 (2011/03/22)
β,β-Dibromoenamides show two different interesting reactivities based on the choice of R group under the reaction conditions. On the basis of mechanistic studies, both reactions proceed via an intermolecular Suzuki-Miyaura C-C coupling and an intramolecular C-O coupling.
Reaction of N-Nitroso-N-benzylformamide with Phenylmagnesium Bromide and Phenyllithium
Nakajima, Masayuki,Anselme, Jean-Pierre
, p. 2492 - 2496 (2007/10/02)
The action of aryl Grignard and lithium reagents on N-nitroso-N-benzylformamide (1) leads to products whose formation can be understood in terms of the intermediacy of benzyldiazotate ion.However, the presence of "hydrogen abstraction" products, e. g., anisole or naphthalene, coupled with the near absence of products traceable to the aldehyde moiety (expected from the attack at the formyl group) with 1 equiv of organometallics, suggests the initial formation of a complex.Possible rationalizations for the formation of the products are presented.
