21473-45-0Relevant articles and documents
The first conversion of primary alkyl halides to nitroalkanes under aqueous medium
Ballini, Roberto,Barboni, Luciano,Giarlo, Guido
, p. 6907 - 6908 (2004)
Primary nitroalkanes and α,ω-dinitroalkanes can be easily obtained in aqueous medium by reaction of the corresponding halo derivatives with silver nitrite. The procedure works well with both alkyl bomide and alkyl iodide and proceeds in satisfactory to good yields even in the presence of other functionalities, minimizing the formation of the undesired alkyl nitrites.
Iridium-catalyzed highly chemoselective and efficient reduction of nitroalkenes to nitroalkanes in water
Chen, Yang,Liu, Changmeng,Xu, Dong,Xu, Jiaxi,Yang, Zhanhui
supporting information, p. 6050 - 6058 (2021/08/23)
An iridium-catalyzed highly chemoselective and efficient transfer hydrogenation reduction of structurally diverse nitroalkenes was realized at very low catalyst loading (S/C = up to 10000 or 20?000), using formic acid or sodium formate as a traceless hydride donor in water. Excellent functionality tolerance is also observed. The turnover number and turnover frequency of the catalyst reach as high as 18?600 and 19?200 h-1, respectively. An inert atmosphere protection is not required. The reactivities of nitroalkenes are dependent on their substitution pattern, and the pH value is a key factor to accomplish the complete conversion and excellent chemoselectivity. Purification of products is achieved by simple extraction without column chromatography. The reduction procedure is facilely amplified to 10 g scale at 10?000 S/C ratio. The potential of this green reduction in enantioselective hydrogenation has been demonstrated.
Nano-NiFe2O4 as an efficient catalyst for regio- and chemoselective transfer hydrogenation of olefins/alkynes and dehydrogenation of alcohols under Pd-/Ru-free conditions
Payra, Soumen,Saha, Arijit,Banerjee, Subhash
, p. 52495 - 52499 (2016/06/13)
Here, we have demonstrated the magnetic nano-NiFe2O4 catalyzed transfer hydrogenation of olefins/alkynes using isopropyl alcohol as a source of hydrogen under ligand/base/Pd-/Ru-metal-free conditions, and dehydrogenation of alcohols under oxidant-free conditions.
Catalyst-free chemoselective reduction of the carbon-carbon double bond in conjugated alkenes with Hantzsch esters in water
He, Qi,Xu, Zhihong,Jiang, Dehong,Ai, Wensi,Shi, Ronghua,Qian, Shan,Wang, Zhouyu
, p. 8671 - 8674 (2014/03/21)
A simple, efficient and green protocol for chemoselective reduction of carbon-carbon double bond in conjugated alkenes with Hantzsch esters is described. Without any additional catalysts, a series of conjugated alkenes with strong electron-withdrawing groups were reduced in water with excellent yield. Functional groups such as nitrile, ester, nitro, fluoro, chloro, bromo, furanyl and benzyl are all tolerated by the reaction conditions employed. The Royal Society of Chemistry.
Useful extensions of the henry reaction: Expeditious routes to nitroalkanes and nitroalkenes in aqueous media
Chandrasekhar, Sosale,Shrinidhi, Annadka
, p. 3008 - 3018 (2014/10/16)
The products of the Henry nitroaldol reaction from nitromethane and several aldehydes were reduced to the corresponding nitroalkanes with (n-Bu) 3SnH in water under microwave irradiation (80 °C/10 min), or dehydrated to the corresponding nitroalkenes with K2CO3 in water (generally 0-5 °C/20 min). Both "one-pot" reactions occur in excellent yields across a range of aliphatic and aromatic (including heteroaromatic) substrates. It seems likely that the deoxygenation of the nitroaldols occurs via coordination of an oxygen atom of the nitro group with a tin atom, which facilitates hydride delivery in the transition state. The elimination of water from the nitroaldols in mild base is likely driven by the stability of the conjugated nitroalkene products. The elimination required workup with 2 N HCl, which likely displaces a nitroalkane-nitroalkene equilibrium towards the latter. These extensions of the Henry reaction lead to products not easily obtained otherwise.
Visible-light-promoted C-C bond cleavage: Photocatalytic generation of iminium ions and amino radicals
Cai, Shunyou,Zhao, Xinyang,Wang, Xinbo,Liu, Qisong,Li, Zigang,Wang, David Zhigang
, p. 8050 - 8053 (2012/08/29)
Photoscissors: Structurally variable and synthetically robust iminium ions and amino radicals species could be simultaneously generated by visible-light-promoted photoredox cleavage of the C-C bonds in simple vicinal diamine precursors under very mild reaction conditions. Copyright
The highly chemoselective transfer hydrogenation of the carbon-carbon double bond of conjugated nitroalkenes by a rhodium complex
Xiang, Jing,Sun, Er-Xiao,Lian, Chun-Xia,Yuan, Wei-Cheng,Zhu, Jin,Wang, Qiwei,Deng, Jingen
experimental part, p. 4609 - 4620 (2012/07/28)
Chemoselective transfer hydrogenation of conjugated nitroalkenes catalyzed by [RhCl2Cp·]2-diamine complex (Cp ·=η5-C5Me5) using HCOOH/Et3N (5:2) (TEAF) as a hydrogen source was realized. A variety of nitrostyrenes, β-methyl nitrostyrenes, and 3-methyl-4-nitro-5-alkenyl- isoxazoles were reduced smoothly in good to excellent yields in short reaction time. Other functional groups are inert under the reaction conditions.
Cascade formation of isoxazoles: Facile base-mediated rearrangement of substituted oxetanes
Burkhard, Johannes A.,Tchitchanov, Boris H.,Carreira, Erick M.
, p. 5379 - 5382 (2011/07/08)
Give me five! Nitro compounds and oxetan-3-one react through an intriguing cascade sequence to give isoxazole-4-carbaldehydes using inexpensive reagents in a one-pot procedure (see scheme; Ms=methanesulfonyl). A variety of 3-substituted isoxazole-4-carbaldehydes were obtained in high overall yields.
Catalyst-free and solventless Hantzsch ester mediated reduction of nitroolefins at elevated temperature
Chauhan, Pankaj,Kaur, Kirandeep,Bala, Neeraj,Kumar, Vikas,Chimni, Swapandeep Singh
experimental part, p. 304 - 309 (2011/05/02)
A catalyst-free and solventless protocol for the reduction of nitroolefins to the corresponding nitroalkanes at 100°C has been developed. Various nitroalkenes have been reduced in good to excellent yield with short reaction times.
Polymer-supported hantzsch 1,4-dihydropyridine ester: An efficient biomimetic hydrogen source for the reduction of ketimines and electron-withdrawing group conjugated olefins
Che, Jun,Lam, Yulin
experimental part, p. 1752 - 1758 (2010/09/11)
A polymer-supported Hantzsch 1,4-dihydropyridine ester was observed to be a useful selective reducing agent for the reduction of ketimines and electron-withdrawing conjugated olefins. The rate of the reduction of electron-withdrawing conjugated olefins is dependent on the nature of the conjugated substituents and could be enhanced by microwave irradiation. The reduction of (Z)-α-cyano-β-bromomethylcinnamates to cyclopropane derivatives using polymer-supported Hantzsch 1,4-dihydropyridine ester was found to proceed stereoselectively and in good yields.
