Studies on selective preparation of aromatic compounds. XII. The selective reductive dehalogenation of some halophenols with zinc powder in basic and acidic media

Tashiro, Masashi; Fukata, Gouki

doi:10.1021/jo00425a014

Cited by 36 publications

(17 citation statements)

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“…In the case of substrates substituted with bromine or iodine upon reduction of corresponding oximes, debromination and deiodination were observed (for a representative example see Figure S4). The reductive dehalogenation upon action of zinc powder in basic and acidic media was already described, and also includes the reaction carried out by zinc dust in the presence of ammonium formate and base (mainly NaOH) [50,51].…”

Section: Chemistrymentioning

confidence: 99%

Phosphonic Acid Analogs of Fluorophenylalanines as Inhibitors of Human and Porcine Aminopeptidases N: Validation of the Importance of the Substitution of the Aromatic Ring

et al. 2020

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A library of phosphonic acid analogs of phenylalanine substituted with fluorine, chlorine and trifluoromethyl moieties on the aromatic ring was synthesized and evaluated for inhibitory activity against human (hAPN) and porcine (pAPN) aminopeptidases. Fluorogenic screening indicated that these analogs are micromolar or submicromolar inhibitors, both enzymes being more active against hAPN. In order to better understand the mode of the action of the most active compounds, molecular modeling was used. It confirmed that aminophosphonic portion of the enzyme is bound nearly identically in the case of all the studied compounds, whereas the difference in activity results from the placement of aromatic side chain of an inhibitor. Interestingly, both enantiomers of the individual compounds are usually bound quite similarly.

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Section: Chemistrymentioning

confidence: 99%

Phosphonic Acid Analogs of Fluorophenylalanines as Inhibitors of Human and Porcine Aminopeptidases N: Validation of the Importance of the Substitution of the Aromatic Ring

et al. 2020

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“…Zinc is well-known as a selective reagent for the reductive dehalogenation of aryl halides in both acidic and basic conditions at or above 20°C. 24 The relative rates for dehalogenation by zinc are reported as I > Br > Cl. Accordingly, at 10-15°C, we observed <5% dechlorination for 4c and 4d, nearly 50% debromination for 4e and 4f, and complete deiodination for 4h by HPLC.…”

Section: A-i 3a-i 4a-i 5 a -I 1a-imentioning

confidence: 99%

Chemoselective Zinc/HCl Reduction of Halogenated β-Nitrostyrenes: Synthesis of Halogenated Dopamine Analogues

Maresh

Ralko

Speltz

et al. 2014

Synlett

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A detailed account regarding the synthesis of 2-and 5-halogenated dopamine is given. The key step is a chemoselective reduction of a nitrostyrene by Zn/HCl at 0 °C. These conditions represent a simple, low-cost alternative to reduction by water-sensitive hydride donors and two-step procedures. Under these conditions, aryl fluoride, chloride, and bromide groups are stable. However, iodine undergoes significant reductive dehalogenation.

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“…When another chlorine atom was introduced at this site, the resulting 2,3‐dichloro‐1‐fluoronaphthalene (98 %) was functionalized after a further deprotonation (intermediate 38 ), at the 4‐position this time. The heavier chlorine atom could be selectively removed by catalytic hydrogenation or reduction with zinc58 to afford the 4‐fluoronaphthalene‐1‐carboxylic acid (87 %) 57…”

Section: Regioflexibility In Hydrogen–metal Exchangementioning

confidence: 99%

The 2×3 Toolbox of Organometallic Methods for Regiochemically Exhaustive Functionalization

Schlosser

2004

Angew Chem Int Ed

283

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This review describes a concept aimed at rational and maximal structure proliferation. To this end, simple aromatic or heterocyclic starting materials, often bulk chemicals, are converted into all regionisomerically possible polar organometallic intermediates (mostly lithiated species), which then may be combined with any of the countless electrophiles to provide attractive new building blocks, particularly functionalized derivatives. The practical implementation relies on a set ("toolbox") of sophisticated recipes developed by mechanistically guided modification of the two most prominent exchange methods used for the generation of polar organometallic compounds: hydrogen-metal and halogen-metal interconversion. These mutant methods ("old methods in a new outfit") amplify the existing options for organic synthesis by ensuring maximum regioflexibility. At the same time they offer new insight into factors that govern organometallic reactivity and provide hints on how to alter or finetune this reactivity judiciously.

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Studies on selective preparation of aromatic compounds. XII. The selective reductive dehalogenation of some halophenols with zinc powder in basic and acidic media

Cited by 36 publications

References 0 publications

Phosphonic Acid Analogs of Fluorophenylalanines as Inhibitors of Human and Porcine Aminopeptidases N: Validation of the Importance of the Substitution of the Aromatic Ring

Phosphonic Acid Analogs of Fluorophenylalanines as Inhibitors of Human and Porcine Aminopeptidases N: Validation of the Importance of the Substitution of the Aromatic Ring

Chemoselective Zinc/HCl Reduction of Halogenated β-Nitrostyrenes: Synthesis of Halogenated Dopamine Analogues

The 2×3 Toolbox of Organometallic Methods for Regiochemically Exhaustive Functionalization

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