111-26-2Relevant articles and documents
Yakhontov et al.
, (1970)
Nanopalladium on amino-functionalized mesocellular foam as an efficient and recyclable catalyst for the selective transfer hydrogenation of nitroarenes to anilines
Verho, Oscar,Nagendiran, Anuja,Tai, Cheuk-Wai,Johnston, Eric V.,Baeckvall, Jan-E.
, p. 205 - 211 (2014)
Herein, we report on the use of nanopalladium on amino-functionalized siliceous mesocellular foam as an efficient heterogeneous catalyst for the transfer hydrogenation of nitroarenes to anilines. In all cases, the protocol proved to be highly selective and favored the formation of the desired aniline as the single product in high yields with short reaction times if naturally occurring and renewable γ-terpinene was employed as the hydrogen donor. Furthermore, the catalyst displayed excellent recyclability over five cycles and negligible leaching of metal into solution, which makes it an eco-friendly and economic catalyst to perform this transformation. The scalability of the protocol was demonstrated with the reduction of 4-nitroanisole on a 2 g scale, in which p-anisidine was isolated in 98 % yield. Copyright
Fe3O4 nanoparticles: A conveniently reusable catalyst for the reduction of nitroarenes using hydrazine hydrate
Kim, Seyoung,Kim, Eunsuk,Kim, B. Moon
, p. 1921 - 1925 (2011)
A magnetic personality: Commercially available Fe3O4 nanoparticles were utilized for efficient nitroarene reductions, and could be recycled up to 10 times using magnetic separation, whilst retaining activity (99 % aniline yield in each case without any side-products). Excellent chemoselectivity for reduction of the nitro versus other functional groups, such as halogen, ester, O-benzyl, and N-Cbz groups, was observed.
PHOTODETOSYLATION OF SULFONAMIDES INITIATED BY ELECTRON TRANSFER FROM AN ANIONIC SENSITIZER
Art, J. F.,Kestemont, J. P.,Soumillion, J. Ph.
, p. 1425 - 1428 (1991)
A new and efficient photosensitized process for the detosylation of a wide variety of sulfonamides is presented.The excited β-naphthoxide anion is used as sensitizer, in methanol as solvent.Electron transfer from the excited naphthoxide anion to the electron-accepting sulfonamide leads, in the presence of sodium borohydride, to the recovering of amines after cleavage of the radical anion.
Soffer
, p. 998 (1957)
Elucidation of reaction scheme describing malondialdehyde - Acetaldehyde - Protein adduct formation
Tuma,Kearley,Thiele,Worrall,Haver,Klassen,Sorrell
, p. 822 - 832 (2001)
Malondialdehyde and acetaldehyde react together with proteins and form hybrid protein conjugates designated as MAA adducts, which have been detected in livers of ethanol-fed animals. Our previous studies have shown that MAA adducts are comprised of two distinct products. One adduct is composed of two molecules of malondialdehyde and one molecule of acetaldehyde and was identified as the 4-methyl-1,4-dihydropyridine-3,5-dicarbaldehyde derivative of an amino group (MDHDC adduct). The other adduct is a 1:1 adduct of malondialdehyde and acetaldehyde and was identified as the 2-formyl-3-(alkylamino)butanal derivative of an amino group (FAAB adduct). In this study, information on the mechanism of MAA adduct formation was obtained, focusing on whether the FAAB adduct serves as a precursor for the MDHDC adduct. Upon the basis of chemical analysis and NMR spectroscopy, two initial reaction steps appear to be a prerequisite for MDHDC formation. One step involves the reaction of one molecule of malondialdehyde and one of acetaldehyde with an amino group of a protein to form the FAAB product, while the other step involves the generation of a malondialdehyde - enamine. It appears that generation of the MDHDC adduct requires the FAAB moiety to be transferred to the nitrogen of the MDA - enamine. For efficient reaction of FAAB with the enamine to take place, additional experiments indicated that these two intermediates likely must be in positions on the protein of close proximity to each other. Further studies showed that the incubation of liver proteins from ethanol-fed rats with MDA resulted in a marked generation of MDHDC adducts, indicating the presence of a pool of FAAB adducts in the liver of ethanol-fed animals. Overall, these findings show that MDHDC - protein adduct formation occurs via the reaction of the FAAB moiety with a malondialdehyde - enamine, and further suggest that a similar mechanism may be operative in vivo in the liver during prolonged ethanol consumption.
Method for preparing amine through catalytic reduction of nitro compound by cyclic (alkyl) (amino) carbene chromium complex
-
Paragraph 0015, (2021/04/17)
The cyclic (alkyl) (amino) carbene chromium complex is prepared from corresponding ligand salt, alkali and CrCl3 and used for catalyzing pinacol borane to reduce nitro compounds in an ether solvent under mild conditions to generate corresponding amine. The method for preparing amine has the advantages of cheap and accessible raw materials, mild reaction conditions, wide substrate application range, high selectivity and the like, and is simple to operate.
Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application
Han, Bo,Jiao, Haijun,Wu, Lipeng,Zhang, Jiong
, p. 2059 - 2067 (2021/09/02)
Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.
Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines
An, Duk Keun,Jaladi, Ashok Kumar,Kim, Hyun Tae,Yi, Jaeeun
, (2021/11/17)
Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.