29865-50-7Relevant academic research and scientific papers
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.
Enantioselective hydrogenation of α,β-disubstituted nitroalkenes
Li, Shengkun,Huang, Kexuan,Zhang, Xumu
supporting information, p. 8878 - 8881 (2014/08/05)
The first highly chemo- and enantioselective hydrogenation of α,β-disubstituted nitroalkenes was accomplished with rhodium/JosiPhos-J2 as a catalyst, with the yield and enantioselectivity of up to 95% and 94%, respectively. The α-chiral nitroalkanes will provide an entry to valuable chiral amphetamines which are otherwise not so easily accessed. This journal is the Partner Organisations 2014.
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.
Asymmetric reduction of nitroalkenes with baker's yeast
Kawai, Yasushi,Inaba, Yoshikazu,Tokitoh, Norihiro
, p. 309 - 318 (2007/10/03)
Various α,β-disubstituted and trisubstituted nitroalkenes were chemoselectively reduced with baker's yeast to the corresponding nitroalkanes. Stereoselectivities of the reduction of α,β-disubstituted nitroalkenes were modest to low, and e.e.s up to 52% were obtained. Trisubstituted nitroalkenes could be reduced to the corresponding nitroalkanes with excellent enantioselectivities, moderate diastereoselectivities and in good yield.
The yeast-mediated reduction of nitrostyrenes in organic solvent systems
Bak, Radoslaw R.,McAnda, Anita F.,Smallridge, Andrew J.,Trewhella, Maurie A.
, p. 1257 - 1260 (2007/10/03)
A range of nitrostyrenes have been reduced with dried baker's yeast in an organic solvent system. It was found that the reduction proceeded smoothly to give the corresponding nitroalkanes in good yield and with higher efficiency than the corresponding aqueous reaction system. No evidence for reduction of the nitro group was observed. In the case of β-methyl nitrostyrenes, racemic mixtures were formed, and it was shown that this is not due to racemization of the product.
REDUCTION OF AROMATIC NITROALKENES WITH BAKER'S YEAST
Takeshita, Mitsuhiro,Yoshida, Sachiko,Kohno, Yoichiro
, p. 553 - 562 (2007/10/02)
Aromatic nitroalkenes were reduced chemoselectively with baker's yeast to give the corresponding nitroalkanes.
