29865-61-0Relevant academic research and scientific papers
Palladium-catalyzed monoarylation of nitroalkanes
Vogl, Erasmus M.,Buchwald, Stephen L.
, p. 106 - 111 (2002)
A general protocol for the Pd-catalyzed-arylation of nitroalkanes is described. Substituted aryl bromides as well as aryl chlorides can be coupled efficiently with a variety of nitroalkanes under mild conditions to selectively yield the monoarylated products. This method tolerates a number of functional groups including ketones, esters, and olefins. Notably, the arylation of nitroalkanes can be effected chemoselectively over ketone and ester arylation.
Micelle-enabled palladium catalysis for convenient sp2-sp3 coupling of nitroalkanes with aryl bromides in water under mild conditions
Brals, Jeremy,Smith, Justin D.,Ibrahim, Faisal,Gallou, Fabrice,Handa, Sachin
, p. 7245 - 7250 (2017/11/09)
The efficacy of custom surfactant FI-750-M, designed to mimic polar solvents such as DMF and 1, 4-dioxane, has been demonstrated with the palladium-catalyzed sp2-sp3 coupling of nitroalkanes to aryl bromides using a heteroleptic palladium catalyst under unprecedentedly mild conditions. Optimized reaction conditions mostly provided good yields up to gram scale, with high selectivity and functional group tolerance for a wide scope of aryl bromides. Use of surfactant FI-750-M makes water the gross reaction medium and enables in-flask recycling. The behavior of the surfactant has been elucidated with DLS and cryo-TEM measurements, and mechanistic investigations have revealed the importance of the π-allyl ligand in the catalytic cycle.
Synthesis of 5-alkyl-5-aryl-γ-lactams from 1-aryl-substituted nitroalkanes and methyl acrylate via Michael addition and reductive lactamization
Xu, Jingjing,Li, Xingyao,Wu, Jinlong,Dai, Wei-Min
, p. 3839 - 3846 (2014/06/09)
A general method for accessing 5-alkyl-5-aryl-γ-lactams has been developed using readily available aryl bromides, nitroalkanes, and methyl acrylate as the starting materials. The palladium-catalyzed arylation of nitroalkanes gave the 1-aryl-substituted nitroalkanes, which underwent the DBU-mediated Michael addition with methyl acrylate at room temperature to afford the methyl 4-aryl-4-nitroalkanoates. The latter were then subjected to the nitro reduction using NaBH4-NiCl2·6H2O in MeOH at 0 °C to furnish, after treatment with aqueous K 2CO3 at room temperature, the 5-alkyl-5-aryl-γ- lactams in good to excellent overall yields. Selected examples of N-alkylation of the γ-lactams were also illustrated.
Synthesis of 5-alkyl-5-aryl-1-pyrroline N-oxides from 1-aryl-substituted nitroalkanes and acrolein via Michael addition and nitro reductive cyclization
Xu, Jingjing,Li, Xingyao,Wu, Jinlong,Dai, Wei-Min
, p. 6384 - 6391 (2015/03/30)
A general method for accessing 5-alkyl-5-aryl-1-pyrroline N-oxides (AAPOs) has been established using readily available aryl bromides, nitroalkanes, and acrolein as the starting materials. The palladium-catalyzed arylation of nitroalkanes gave the 1-aryl-substituted nitroalkanes, which underwent the Et3N-catalyzed Michael addition with acrolein at room temperature to afford the 4-aryl-4-nitroaldehydes. The latter were then subjected to the nitro reductive cyclization using Zn-HOAc in EtOH at 0 °C followed by warming the reaction mixture to room temperature for 24 h, furnishing the 5-alkyl-5-aryl-1-pyrroline N-oxides in good overall yields. Selected examples of 1,3-dipolar cycloaddition of the cyclic nitrones with methyl methacrylate were also described.
A simple and highly efficient procedure for the preparation of aliphatic nitro compounds directly from alcohols
Baruah, Apurba,Kalita, Biswajit,Barua, Nabin C.
, p. 1064 - 1066 (2007/10/03)
A simple and highly efficient one-pot synthesis of aliphatic nitro compounds from the corresponding alcohols with NaNO2-AcOH-HCl system is described.
