37567-58-1Relevant 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.
Bioinspired Nitroalkylation for Selective Protein Modification and Peptide Stapling
Adebomi, Victor,Mahesh, Sriram,Muneeswaran, Zilma P.,Raj, Monika
supporting information, p. 2793 - 2801 (2020/01/25)
Nitroalkanes react specifically with aldehydes, providing rapid, stable, and chemoselective protein bioconjugation. These nitroalkylated proteins mimic key post-translational modifications (PTMs) of proteins and can be used to understand the role of these
S-benzyl isothiouronium chloride as a recoverable organocatalyst for the reduction of conjugated nitroalkenes with Hantzsch ester
Nguyen, Quynh Pham Bao,Kim, Jae Nyoung,Kim, Taek Hyeon
supporting information; experimental part, p. 6513 - 6516 (2012/08/28)
The reduction of conjugated nitroalkenes into nitroalkanes with Hantzsch ester using S-benzyl isothiouronium chloride as a recoverable organocatalyst was successfully accomplished with high yield and excellent chemoselectivity.
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.
Organocatalytic biomimetic reduction of conjugated nitroalkenes
Zhang, Zhiguo,Schreiner, Peter R.
, p. 2559 - 2564 (2008/03/13)
A thiourea-catalyzed biomimetic reduction of conjugated nitroalkenes has been developed. Various aromatic and aliphatic conjugated nitroalkenes can be reduced to give the respective nitroalkanes with good yields under mild conditions. This protocol is not only practical, but may also provide insight into the mechanisms of redox transformations in biological systems. Georg Thieme Verlag Stuttgart.
Borrowing hydrogen: Iridium-catalysed reactions for the formation of C-C bonds from alcohols
Black, Phillip. J.,Cami-Kobeci, Gerta,Edwards, Michael G.,Slatford, Paul A.,Whittlesey, Michael K.,Williams, Jonathan M. J.
, p. 116 - 125 (2007/10/03)
Alcohols have been employed as substrates for C-C bond-forming reactions which involve initial activation by the temporary removal of hydrogen to form an aldehyde. The intermediate aldehyde is converted into an alkene via a Horner-Wadsworth-Emmons reaction, nitroaldol and aldol reactions. The 'borrowed hydrogen' is then returned to the alkene to form a C-C bond. The Royal Society of Chemistry 2006.
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.
In Situ Generation and Synthetic Application of 2-Phenylbenzimidazoline to the Selective Reduction of Carbon-Carbon Double Bonds of Electron-Deficient Olefins
Chikashita, Hidenori,Nishida, Shuichi,Miyazaki, Makoto,Morita, Yasuhiro,Itoh, Kazuyoshi
, p. 737 - 746 (2007/10/02)
2-Phenylbenzimidazoline (PBI) as a mild, selective, and convenient reducing agent was efficiently generated in situ from o-phenylenediamine and benzaldehyde in alcohols.A generally applicable method for the selective reduction of carbon-carbon double bonds of a variety of electron-deficient olefins with an alcoholic solution of PBI is described.The reduction of α,β-unsaturated ketones to the corresponding saturated ketones could also be accomplished (but, less effectively) with PBI with the aid of a Lewis-acid catalyst. 1-Methyl-2-(o-nitrophenyl)benzimidazoline prepared and isolated by the reaction of o-nitrobenzaldehyde with N-methyl-o-phenylenediamine reduced benzylidenemalononitrile to give benzylmalononitrile and 1-methyl-2-(o-nitrophenyl)benzimidazoline in high yields.This shows the validity of PBI to be the actual reducing species in the present reduction system.From a mechanistic study, the present reductions could be interpreted in terms of a mechanism involving a synchronous transport of a pair of hydrogens or a sequential transfer of a hydride and a proton from PBI to the olefins.
Isolation and Structure of Thalictoside
Ina, Hiroji,Iida, Hideo
, p. 726 - 729 (2007/10/02)
Thalictoside (1), a novel glycoside containing a nitro group, was isolated from Thalictrum aquilegifolium and the structure was shown to be 4-hydroxy-1-(2-nitroethyl)benzene 4-O-β-D-glucopyranoside on the basis of chemical transformations, spectral analys
