- A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, N-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride
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The first mild, in situ, single-pot, high-yielding well-screened copper (II) salt-based catalyst system utilizing the hydrogen surrogacy of sodium borohydride for selective hydrogenation of a broad range of nitro substrates into the corresponding amine under habitancy of water or methanol like green solvents have been described. Moreover, this catalytic system can also activate various functional groups for hydride reduction within prompted time, with low catalyst-loading, without any requirement of high pressure or molecular hydrogen supply. Notably, this system explores a great potential to substitute expensive traditional hydrogenation methodologies and thus offers a greener and simple hydrogenative strategy in the field of organic synthesis.
- Kalola, Anirudhdha G.,Prasad, Pratibha,Mokariya, Jaydeep A.,Patel, Manish P.
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supporting information
p. 3565 - 3589
(2021/10/12)
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- A magnetic nanoparticle catalyzed eco-friendly synthesis of cyanohydrins in a deep eutectic solvent
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Magnetic Fe3O4 nanoparticles in deep eutectic solvents (DESs) have been regard as excellent catalysts for highly efficient cyanosilylation of various aldehydes and epoxides using trimethylsilyl cyanide TMSCN in high yields with excellent selectivity. Fe3O4 nanoparticles were synthesized and applied as a catalyst for the preparation of a wide variety of cyanohydrins (α-hydroxy nitriles and β-hydroxy nitriles) in readily available urea-choline chloride deep eutectic solvent DES as the most promising environmentally benign and cost-effective green solvent. Magnetic DES operates at very mild reaction conditions and can be easily recycled without significant loss of its catalytic activity.
- Azizi, Najmedin,Rahimi, Zahra,Alipour, Masoumeh
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p. 61191 - 61198
(2015/07/28)
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- Facile synthesis of an organic-inorganic nanocomposite, PEG-silica, by sol-gel method; Its characterization and application as an efficient catalyst in regioselective nucleophilic ring opening of epoxides: Preparation of β-azido alcohols and β-cyanohydrin
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The sol-gel method was used for the synthesis of a PEG-silica hybrid. In order to introduce PEG into the cavities of silica gel, first, the bis(3-trimethoxysilylpropyl)-polyethylene glycol precursor was synthesized by the reaction of 3-chloropropyltrimeth
- Kiasat, Ali Reza,Nazari, Simin,Davarpanah, Jamal
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p. 124 - 130
(2014/03/21)
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- Unexpected cleavage of 2-azido-2-(hydroxymethyl)oxetanes: Conformation determines reaction pathway?
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An unanticipated cleavage of 2-azido-2-(hydroxymethyl)oxetanes is reported. In attempts to oxidize the title oxetanyl alcohols to the corresponding carboxylic acids with RuO4, cleaved nitriles were formed as the sole isolable products, while a
- Farber, Elisa,Herget, Jackson,Gascon, Jose A.,Howell, Amy R.
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supporting information; experimental part
p. 7565 - 7572
(2011/02/26)
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- An environmentally benign catalytic method for efficient and selective nucleophilic ring opening of oxiranes by zirconium tetrakis(dodecyl Sulfate)
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An operationally simple and environmentally benign protocol for a highly regio- and chemoselective preparation of β-substituted alcohols by means of ring-opening reactions of oxiranes with various aliphatic alcohols, H 2O, NaN3 , and NaCN as nucleophiles in the presence of catalytic amounts of zirconium tetrakis(dodecyl sulfate) as Lewis acid/surfactant-combined catalysts (LASCs) was developed. The high efficiency of the catalyst was confirmed by the high product yields obtained within desired times and, in particularly by the reusability of the ZrIV complex.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Aliabadi, Marzieh
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scheme or table
p. 405 - 413
(2010/05/19)
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- LiOH-catalyzed simple ring opening of epoxides under solvent-free conditions
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LiOH has been found to be a very simple and selective catalyst for the rapid and mild synthesis of β-hydroxy sulfides and β-hydroxyl nitriles by ring opening of epoxides with aromatic, aliphatic, and heterocyclic thiols and trimethylsilyl cyanide at room temperature under solvent free conditions. All the reactions proceeded satisfactorily in short times and afforded the corresponding products in good to excellent yields with high regioselectivity and chemoselectivity under mild reaction conditions. Copyright Taylor & Francis Group, LLC.
- Azizi, Najmedin,Khajeh-Amiri, Alireza,Ghafuri, Hossein,Bolourtchian, Mohammad
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experimental part
p. 1550 - 1557
(2010/09/06)
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- Biocatalytic cascade for the synthesis of enantiopure β-azidoalcohols and β-hydroxynitriles
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A three-step, two-enzyme, one-pot reaction sequence starting from prochiral a-chloroketones leading to enantiopure (3- azidoalcohols and (3-hydroxynitriles is described. Asymmetric bioreduction of a-chloroketones by hydrogen transfer catalysed by an alcohol dehydrogenase (ADH) established the stereogenic centre in the first step to furnish enantiopure chlorohydrin intermediates. Subsequent biocatalysed ring closure to the epoxide and nucleophilic ring opening with azide, N3-, or cyanide, CN-, both catalysed by a nonselective halohydrin dehalogenase (Hhe) proceeded with full retention of configuration to give enantiopure (-azidoalcohols and (3-hydroxynitriles, respectively. Both enantiomers of various optically pure (-azidoalcohols and (-hydroxynitriles were synthesised.
- Schrittwieser, Joerg H.,Lavandera, Ivan,Seisser, Birgit,Mautner, Barbara,Kroutil, Wolfgang
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experimental part
p. 2293 - 2298
(2009/08/17)
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- Esters of 2-phenylalkanenitriles and antifungal compositions containing them
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Esters of 2-phenylalkanenitriles, such as 3-acetoxy-2-(2-chloro-5-(difluoromethoxy)phenyl)propanenitrile and 3-acetoxy-2-(4-chlorophenyl)propanenitrile, and compositions containing such esters, are useful as fungicides at very low concentrations.
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Page/Page column 7
(2008/12/06)
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- Micellar media for the efficient ring opening of epoxides with CN-, N3-, NO3-, NO2-, SCN-, Cl- and Br- catalyzed with Ce(OTf)4
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Micellar media are introduced for the efficient ring opening of epoxides with sodium salts of nucleophiles such as CN, N3-, NO3-, NO2, SCN, Br and Cl-, catalyzed with Ce(OTf)4. This method is an efficient procedure for the synthesis of different β-substituted alcohols under mild reaction conditions. The reaction with SCN- is an easy procedure for the high yielding preparation of epoxy sulfides.
- Iranpoor, Nasser,Firouzabadi, Habib,Shekarize, Marzieh
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p. 724 - 727
(2007/10/03)
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- Highly regioselective conversion of epoxides to β-hydroxy nitriles with cyanide exchange resin
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A simple and regioselective method is described for the efficient conversion of epoxides to β-hydroxy nitriles using Amberlite IRA-400 supported cyanide. The reactions occur in the absence of catalyst and furnish the corresponding β-hydroxy nitriles in high yields.
- Tamami,Iranpoor,Rezaei
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p. 3153 - 3157
(2007/10/03)
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- An Epoxide Ring-Opening Reaction via Hypervalent Silicate Intermediate: Synthesis of Statine
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The azide- and cyanide-opening reaction of epoxide with TBAF and TMSN 3 in THF or TBAF and TMSCN in MeCN occurred regioselectively to afford β-hydroxy azides and cyanides in good yield. These hypervalent silicates have been shown to be highly effective as nucleophilic azide and cyanide donors under mild conditions. This methodology has been applied to the preparation of statine.
- Konno, Hiroyuki,Toshiro, Emi,Hinoda, Naoyuki
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p. 2161 - 2164
(2007/10/03)
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- A mild and selective cleavage of p-methoxybenzyl Ethers by CBr4-MeOH
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p-Methoxybenzyl ethers were selectively deprotected to the corresponding alcohols and phenols in high yields by CBr4 in refluxing methanol under neutral reaction conditions.
- Yadav,Reddy, B. V. Subba
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p. 566 - 567
(2007/10/03)
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- Ring opening of epoxides with sodium cyanide catalyzed with Ce(OTf)4
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Efficient and regioselective conversion of epoxides to β-hydroxy nitriles with sodium cyanide in the presence of catalytic amounts of Ce(OTf)4 is described under solvent free conditions.
- Iranpoor,Shekarriz
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p. 2249 - 2254
(2007/10/03)
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- Easy Direct Stereo- and Regioselective Formation of β-Hydroxy Nitriles by Reaction of 1,2-Epoxides with Potassium Cyanide in the Presence of Metal Salts
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A simple efficient, anti stereoselective, and highly regioselective method for the synthesis of β-hydroxy nitriles by the direct opening of 1,2-epoxides with KCN in acetonitrile, in the presence of metal salts, is described.This new method appears to be competitive with the other methods previously reported. Key words: β-hydroxy nitriles; epoxide opening reactions; regioselectivity; catalysts.
- Chini, Marco,Crotti, Paolo,Favero, Lucilla,Macchia, Franco
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p. 4775 - 4778
(2007/10/02)
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- Total Syntheses of Substituted Hydrobenzindenes and Hydrophenanthrenes
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A new method, involving addition of ethyl m-methoxyatropate (10) and m-methoxyatroponitrile (12) to or condensation of the cyanohalides (18 and 20) with diones (33 and 34) and ethyl methyl 3-oxoadipate (56), has been developed for the synthesis of 1,2,3,4
- Banerjee, D.K.,Kasturi, T.R.,Purushotham, V.
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p. 395 - 411
(2007/10/02)
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