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

Cho, Byung Tae; Kang, Sang Kyu; Kim, Min Sung; Ryu, Soo Ryeon; An, Duk Keun

doi:10.1016/j.tet.2006.05.083

Cited by 54 publications

(27 citation statements)

References 11 publications

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“…This reduction was carried out according to the method as previously described [9]. A mixture of (2) (10 mmol) and NaBH 4 (10 mmol) was ground with an agate mortar and a pestle for 10 min.…”

Section: Synthesis Of Veratryl Alcohol (3)mentioning

confidence: 99%

Synthesis and Heme Polymerization Inhibitory Activity (HPIA) Assay of Antiplasmodium of (1)-N-(3,4-Dimethoxybenzyl)-1,10-Phenanthrolinium Bromide from Vanillin

Fitriastuti¹,

Mardjan²,

Jumina³

et al. 2014

Indones. J. Chem.

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The synthesis of (1)-N-(3,4-dimethoxy-benzyl h to yield veratraldehyde in the form of light yellow solid (79% yield). Methylation product was reduced using sodium borohydride (NaBH 4 ) with grinding method and yielded veratryl alcohol in the form of yellow liquid (98% yield). Veratryl alcohol was brominated using PBr 3 to yield yellowish black liquid (85% yield). The final step was benzylation of 1,10-phenanthroline monohydrate with the synthesized veratryl bromide under reflux condition in acetone for 14 h to afford (1)-N-(3,4-dimethoxy-benzyl)-1,10-phenanthrolinium bromide (84%) as yellow solid with melting point of 166-177°C. The structures of products were characterized by FT-IR, GC-MS and

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Section: Synthesis Of Veratryl Alcohol (3)mentioning

confidence: 99%

Synthesis and Heme Polymerization Inhibitory Activity (HPIA) Assay of Antiplasmodium of (1)-N-(3,4-Dimethoxybenzyl)-1,10-Phenanthrolinium Bromide from Vanillin

Fitriastuti¹,

Mardjan²,

Jumina³

et al. 2014

Indones. J. Chem.

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“…[5a] More recently, solvent-free reductions of carbonyl compounds by sodium borohydride with added solid acids such as boric acid, benzoic acid, and 4-toluenesulfonic acid monohydrate [6] or wet silica have been reported. [7] All of these techniques, however, were not waste free, and the yields were less than quantitative.…”

Section: Introductionmentioning

confidence: 99%

Sodium Tetraalkoxyborates: Intermediates for the Quantitative Reduction of Aldehydes and Ketones to Alcohols through Ball Milling with NaBH₄

et al. 2009

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Stoichiometric molecular solid‐state vibrational ball milling, solvent‐free kneading ball milling, and mechanochemical ball milling of varied aldehydes and ketones with unmodified sodium borohydride under temperature control uses all hydrogen atoms of the reducing agent in fast reactions. It provides quantitative yields of thermally stable sodium tetraalkoxyborates. The easily isolated solids are extremely sensitive towards hydrolysis, leading to quantitative yields of the corresponding alcohols. The rapid syntheses are regiospecific and stereoselective. Varied substituents are not attacked, including the bromine of α‐bromo ketones. Conjugated aldehydes and ketones provide quantitative yields of the allylic alcohols free of contamination by saturated alcohols that would occur by reaction in solution. Depending on the stoichiometric ratio, benzil is quantitatively reduced to benzoin (4:1 ratio) or dihydrobenzoin (2:1 ratio). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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“…To this end, b-keto esters 21 were treated with five equivalents of NaBH 4 at 0 8C for 8 h, thus leading to, for example, the corresponding b-hydroxy esters 43 a, b after acidic workup in moderate-to-good yields (Scheme 9). [24] A small number of b-keto esters were further converted into the corresponding acids by stirring overnight in 15 % TFA in an acetonitrile/H 2 O mixture. Direct reversephase HPLC purification without previous workup led to the b-keto acids 44 in 75-81 % yield (Scheme 9).…”

Section: Full Papermentioning

confidence: 99%

Biology‐Oriented Combined Solid‐ and Solution‐Phase Synthesis of a Macroline‐Like Compound Collection

Wilk

Nören‐Müller

Kaiser

et al. 2009

Chemistry A European J

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Macrolines constitute a class of natural products that has more than 100 members and displays diverse biological activities. These compounds feature a cycloocta[b]indole scaffold that represents an interesting target structure for biology-oriented synthesis (BIOS). We have presented a solid-phase synthesis of isomerically pure cycloocta[b]indoles by employing the Pictet-Spengler reaction and the Dieckmann cyclization as key steps. The scope of this reaction sequence was investigated in more detail by using various additional diversification procedures, such as Pd-catalyzed Sonogashira or Suzuki couplings on a solid phase, thus allowing, for example, the generation of 10-substituted cycloocta[b]indole derivatives. Finally, solution-phase decoration of the cycloocta[b]indole skeleton by reduction and saponification was evaluated, thereby further extending the scope of the solid-phase synthesis.

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

Cited by 54 publications

References 11 publications

Synthesis and Heme Polymerization Inhibitory Activity (HPIA) Assay of Antiplasmodium of (1)-N-(3,4-Dimethoxybenzyl)-1,10-Phenanthrolinium Bromide from Vanillin

Synthesis and Heme Polymerization Inhibitory Activity (HPIA) Assay of Antiplasmodium of (1)-N-(3,4-Dimethoxybenzyl)-1,10-Phenanthrolinium Bromide from Vanillin

Sodium Tetraalkoxyborates: Intermediates for the Quantitative Reduction of Aldehydes and Ketones to Alcohols through Ball Milling with NaBH₄

Biology‐Oriented Combined Solid‐ and Solution‐Phase Synthesis of a Macroline‐Like Compound Collection

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

Cited by 54 publications

References 11 publications

Synthesis and Heme Polymerization Inhibitory Activity (HPIA) Assay of Antiplasmodium of (1)-N-(3,4-Dimethoxybenzyl)-1,10-Phenanthrolinium Bromide from Vanillin

Synthesis and Heme Polymerization Inhibitory Activity (HPIA) Assay of Antiplasmodium of (1)-N-(3,4-Dimethoxybenzyl)-1,10-Phenanthrolinium Bromide from Vanillin

Sodium Tetraalkoxyborates: Intermediates for the Quantitative Reduction of Aldehydes and Ketones to Alcohols through Ball Milling with NaBH4

Biology‐Oriented Combined Solid‐ and Solution‐Phase Synthesis of a Macroline‐Like Compound Collection

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Sodium Tetraalkoxyborates: Intermediates for the Quantitative Reduction of Aldehydes and Ketones to Alcohols through Ball Milling with NaBH₄