Indium-mediated one-pot reductive conversion of nitroarenes to N-arylacetamides

Kim, Byeong Hyo; Han, Rongbi; Piao, Fengyu; Jun, Young Moo; Baik, Woonphil; Lee, Byung Min

doi:10.1016/s0040-4039(02)02479-6

Cited by 36 publications

(12 citation statements)

References 20 publications

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“…16 This protocol generally involves two steps; the rst step is the reduction of nitroarenes to the corresponding anilines and the second step is the carbonylation of anilines to the corresponding amides. Indium/AcOH, 17 Ni 2 B@Cu 2 O/NaBH 4 , 18 Pd-C/ NaBH 4 19 and Fe 3 O 4 @Cu(OH) x /NaBH 4 20 are some of the systems which have been reported for direct transformation of nitroarenes to amides. Although most of the published methods are useful synthetic methods, they generally suffer from long reaction times, unsatisfactory yields of the products and use of unrecoverable catalysts.…”

Section: Introductionmentioning

confidence: 99%

A new bifunctional heterogeneous nanocatalyst for one-pot reduction-Schiff base condensation and reduction–carbonylation of nitroarenes

2019

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Section: Introductionmentioning

confidence: 99%

A new bifunctional heterogeneous nanocatalyst for one-pot reduction-Schiff base condensation and reduction–carbonylation of nitroarenes

2019

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“…), ([Fe–AcOH]/100–110°C), ([In‐Ac 2 O–AcOH]/CH 3 OH/r.t. ), ([SmI 2 ‐EtOAc]/THF/under N 2 (g)/r.t. ), ([Sm‐Ac 2 O–AcOH]/CH 3 OH/r.t.…”

Section: Resultsmentioning

confidence: 99%

Application of Cu(Hdmg)₂ as a simple and cost‐effective catalyst for the convenient one‐pot reductive acetylation of aromatic nitro compounds

Zeynizadeh

Mousavi

Zarrin

2019

J Chinese Chemical Soc

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In this article, we have developed a novel and simple one‐pot reductive acetylation of aromatic nitro compounds with sodium borohydride (NaBH4) in ethyl acetate (EtOAc) under reflux conditions in the presence of the bis(dimethylglyoximato)copper(II) complex [Cu(Hdmg)2] as an efficient and cost‐effective copper‐containing catalyst. Notably, using the above‐mentioned one‐pot reaction, the corresponding acetamide derivatives were obtained in high to excellent yields.

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“…More recently, N -aryl acetamides were prepared in excellent yields from nitroarenes in the presence of acetic anhydride, acetic acid and In in a one -pot procedure. As an example of the use this method, the nitro arene (20) was transformed into the amine (21) in high yield (Scheme 17.10 ) [39] .…”

Section: Reduction Of Nitro Compoundsmentioning

confidence: 99%

Dissolving Metals

Yus

Foubelo

2008

Modern Reduction Methods

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17 IntroductionDissolving metals have been used extensively as reducing agents for more than a century but today they have been partially displaced from the central fi eld of organic synthesis by the use of other more selective methodologies, such as metal hydrides [1] and catalytic hydrogenations [2] . However, dissolving metals are still of interest for the selective reduction of specifi c polar functional groups (such as hindered cyclic ketones) and the reductive cleavage of some activated bonds [3] .Regarding the mode of action of electropositive metals in reduction processes, it is generally assumed that an initial single -electron transfer ( SET ) from the metal to the organic substrate takes place to give a radical anion [4] . Depending on the organic substrate and on the reaction conditions (mostly on the solvent), the highly reactive resulting radical anion can then decompose via a number of different routes. For instance, for compounds (I) with multiple C = X bonds (X = CR 2 , O, NR, S), the radical anion (II) could be protonated in the presence of a proton source (the solvent) to give a new radical (III) , which after a further SET from the metal, and further protonation of the resulting anion (IV) , would lead to the reduced product (V) . In the absence of a proton source, coupling of two radical anions (II) can occur to give fi rst the dianionic species (VI) and, after hydrolysis, compounds of type (VII) . Organic substrates (VIII) with activated bonds X − Y (X = CR 3 , OR, SR, NR 2 ; Y = CR 3 , OR, SR, NR 2 , Hal (F, Cl, Br, I)) also undergo reductive cleavage by means of electropositive metals through a SET mechanism. In this case, the initially formed radical anion (IX) suffers the activated X − Y bond scission to generate a radical (X) and an anion (XI) . Radical (X) would be converted to an anion after a new electron transfer from the metal, and fi nal protonation would yield the corresponding reduced products (XII) and (XIII) , respectively (Scheme 17.1 ).Most of the reductions by means of dissolving metals have been performed using highly electropositive metals, such as Li, Na and K, in liquid NH 3 as solvent. Less electropositive metals (Mg, Ca, Sr, Ba, Ni, Cu, Zn, In, Sn, Pb) have also been used, so by choosing the appropriate metal, solvent and cosolvent it is possible to

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Indium-mediated one-pot reductive conversion of nitroarenes to N-arylacetamides

Cited by 36 publications

References 20 publications

A new bifunctional heterogeneous nanocatalyst for one-pot reduction-Schiff base condensation and reduction–carbonylation of nitroarenes

A new bifunctional heterogeneous nanocatalyst for one-pot reduction-Schiff base condensation and reduction–carbonylation of nitroarenes

Application of Cu(Hdmg)₂ as a simple and cost‐effective catalyst for the convenient one‐pot reductive acetylation of aromatic nitro compounds

Dissolving Metals

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Indium-mediated one-pot reductive conversion of nitroarenes to N-arylacetamides

Cited by 36 publications

References 20 publications

A new bifunctional heterogeneous nanocatalyst for one-pot reduction-Schiff base condensation and reduction–carbonylation of nitroarenes

A new bifunctional heterogeneous nanocatalyst for one-pot reduction-Schiff base condensation and reduction–carbonylation of nitroarenes

Application of Cu(Hdmg)2 as a simple and cost‐effective catalyst for the convenient one‐pot reductive acetylation of aromatic nitro compounds

Dissolving Metals

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Application of Cu(Hdmg)₂ as a simple and cost‐effective catalyst for the convenient one‐pot reductive acetylation of aromatic nitro compounds