Reduction of ester groupings in porphyrins with sodium borohydride

Reduction of the corresponding acyl derivatives by means of sodium borohydride [1, 2] is usually employed to obtain porphyrins with -hydroxyalkyl substituents.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, p. 860, June, 1973.     

Ruthenium catalysed reduction of alkenes using sodium borohydride

The reduction of alkenes has been achieved using NaBH₄ as the reducing agent using 0.5-1.0 mol % Ru(PPh₃)₄H₂ in the presence of water.     

Selective reduction of vinylhydroxyphenyl azomethines by sodium borohydride

Conclusions Vinylhydroxyphenyl azomethines are reduced by sodium borohydride at room temperature only at the azomethine group.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2076–2078, September, 1978.     

Photo-enhanced reduction of carbonyl compounds by sodium borohydride

The reduction of ketones and some esters by sodium borohydride is dramatically accelerated by uv irradiation. The reaction seems to proceed from the (n, π) excited state of the carbonyl compound. The photocatalytic effect is dependent on the solvent polarity and substituents on aromatic carboxylic acids and alcohols of esters.     

Investigations of polyaniline-platinum composites prepared by sodium borohydride reduction

Two procedures were applied for the preparation of polyaniline (PANI)-Pt composites in aqueous solutions using sodium borohydride as the reducing agent. The first one involved reduction of Pt ions originating from PtCl₄ conducted in the presence of PANI. The second was a two-step method in which doping of PANI with Pt-containing anions was followed by their reduction. The composites containing various amounts of Pt were obtained. They were characterized by X-ray diffraction, X-ray photoelectron and IR spectroscopies. This allowed to establish differences in the efficiency of both methods of composite preparation. It was also found that the composites show mainly redox activity in catalytic isopropyl alcohol conversion.     

The stereoselective reduction of α-aminodeoxybenzoin derivatives with sodium borohydride

Total stereoselectivity is observed in the sodium borohydride reduction of α-aminodeoxybenzoins and their hydrochlorides in various hydroxylic solvents. RS - SR isomer (erythro) was the only aminoalcohol obtained.     

Regioselective reduction of 2-cyanoprop-2-enethioamides with sodium borohydride

Treatment of 2-cyanoprop-2-enethioamides with NaBH₄ in EtOH gave C-alkylated cyanothioacetamides in 62–69% yields.     

Microdetermination of carbonyl compounds by reduction with alkaline sodium borohydride

Summary Alkaline sodium borohydride has been employed as a reducing reagent for the titrimetric determination of compounds containing the carbonyl function. The sample is dissolved in methanol and is then reduced with alkaline sodium borohydride. After completion of the reaction, the excess sodium borohydride is back titrated against standardized hydrochloric acid solution using methyl red as indicator. The stoichiometry between the carbonyl function and sodium borohydride is 41.

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Zusammenfassung Natriumborhydrid dient als Reduktionsmittel zur Titration von Carbonylverbindungen. Die Probe wird in Methanol gelöst und dann mit alkalischem Natriumborhydrid reduziert. Nach Ablauf der Reaktion wird der Überschuß mit Salzsäure gegen Methylrot zurücktitriert. Carbonylverbindung und Natriumborhydrid reagieren im Verhältnis 41.

     

Enantioselective reduction of ketophosphonates using chiral acid adducts with sodium borohydride

A method for asymmetric reduction of α-and β-ketophosphonates using a chiral complex prepared from sodium borohydride and D-or L-tartaric acid is developed. Reduction of α-or β-ketophosphonates by these reagents led to formation of corresponding (S)-or (R)-hydroxyphosphonates. Reduction of chiral di(1R,2S,5R)-menthylketophosphonates by the chiral complex NaBH₄/(R,R)-tartaric acid due to the dual compliant asymmetric induction resulted in increased stereoselectivity of the reaction and led to formation of the hydroxyphosphonates with ee 90% or higher. On the other hand, reduction of di(1R,2S,5R)-methylketophosphonates by the chiral complex NaBH₄/(S,S)-tartaric acid proceeded as non-compliant dual asymmetric induction and resulted in decreased reaction stereoselectivity leading to formation of hydroxyphosphonates with ～45–60% ee. The developed methodology was applied to the synthesis of (R)-phosphocarnitine in multigram amounts.     

Solvent-free reduction of aldehydes and ketones using solid acid-activated sodium borohydride

A simple and convenient procedure for the reduction of aldehydes and ketones with sodium borohydride activated by solid acids such as boric acid, benzoic acid, and p-toluenesulfonic acid monohydrate under solvent-free conditions is described.     

Preparation of aldehydes by sodium aluminum hydride reduction of carboxylate esters

Summary Sodium aluminum hydride reduces carboxylate esters and lactones in good yield to the corresponding aldehydes and hydroxy aldehydes.Translated from Izvestiya Akademii Nauk SSR, Seriya Khimicheskaya, No. 5, pp. 926–928, May, 1964     

Ultrafast room-temperature reduction of graphene oxide by sodium borohydride,sodium molybdate and hydrochloric acid

Since graphene-based materials have shown great potential in many fields,it is important to explore ultrafast and high-efficient methods to synthesize reduced graphene oxide(rGO) using inexpensive reducing agents under mild conditions.Here,we reported a novel method for the ultrafast chemical reduction of graphene oxide(GO) at room temperature using sodium borohydride(NaBH₄),sodium molybdate(Na₂MoO₄) and hydrochloric acid(HCl).The reduction was carried out within 2 min.A series of characterization results revealed that the obtained reduced graphene oxide has higher reduction degree than that synthesized by NaBH₄ alone at high temperature.Moreover,rGO electrode based on the present reducing method exhibited a superior specific capacitance of 139.8 F/g at a current density of1 A/g,indicating that it can be used as electrode materials for supercapacitors.     

One-pot carbonyl reduction and carbonate formation using sodium borohydride in dialkyl carbonate solvents

Preparation of mixed carbonates proceeded in one step from ketones and aldehydes via treatment with NaBH₄ in dimethyl or diethyl carbonate solvent at elevated temperatures. This is an efficient and convenient alternative to the traditional two-step sequence of carbonyl reduction to alcohol and subsequent carbonate formation by treatment with an alkyl chloroformate. 25 examples are presented from 49 to 92% yield, highlighting the versatility of this reaction.     

Solution conformation of the two alditols obtained by sodium borohydride reduction of N-acetylneuraminic acid

The stereochemistries and the conformations of the two alditols1 and2 (3:2) obtained upon reduction of N-acetylneuraminic acid were determined in aqueous solution using proton and carbon nuclear magnetic resonance spectroscopy. Molecular mechanics calculation was proved to be not applicable onto alditols, if the balance of the conformational equilibrium is maintained by 1,3-diaxial interactions. No measurable amount of the -N-acetylneuraminic acid like triple bent alditol form, which is believed to be the substrate of theClostridium perfringens lyase, could be detected in solution. In aqueous solution compound2 is present in its extended form. One can expect that the necessary energy contribution of approximately 1 kcal to fold2 into the form which is recognized by the enzyme is easily available.

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Zur Konformation der beiden durch Reduktion von N-Acetyl-Neuraminsäure mit Natriumborhydrid erhaltenen Alditole in wäßriger Lösung

Zusammenfassung Bei der Reduktion von N-Acetyl-Neuraminsäure mit Natriumborhydrid in wäßriger Lösung werden die Alditole1 und2 im Verhältnis 3:2 gebildet. Die stereochemische Zuordnung und die Konformation der beiden Epimere in Lösung wurden mit Hilfe einer NMR-Analyse durchgeführt. In Ergänzung dazu wurde die Anwendbarkeit von Rechnungen des Typus Molekulare Mechanik auf flexible Moleküle dieser Art untersucht und gefunden, daß Populationen von Konformationen, welche primär durch 1,3-diaxiale Wechselwirkungen determiniert sind, durch Rechnungen dieses Typs nicht vorhersagbar sind. In wäßriger Lösung liegt Verbindung2 in gestreckter Form vor. Die aus2 ableitbare -N-Acetylneuraminsäure ähnliche Konformation, welche dem Substrat derClostridium perfringens-Lyase entspricht, ist um 1 kcal energiereicher als die der gestreckten Form und liegt in Lösung nicht in meßbaren Mengen vor. Man kann erwarten, daß dieser Energiebeitrag unschwer bei der Einbettung in die Enzymtasche der Lyase aufgebracht werden kann.