Copper-catalyzed cyanation of aryl iodides with α-cyanoacetates via C–CN bond activation

Zhang, Songlin; Huang, Lu

doi:10.1039/c5ob01675d

Cited by 29 publications

(11 citation statements)

References 57 publications

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“…Mechanistic studies clearly show that the aryl aldehydes were key intermediates formed during the tandem catalytic process involving cyanation of the electron‐rich arenes (See Figure 32). [43] …”

Section: Organic Cyanide Sourcementioning

confidence: 99%

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Copper Mediated Chemo‐ and Stereoselective Cyanation Reactions

et al. 2021

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Earth‐abundant transition metal based catalytic materials can become pivotal for clean chemical manufacturing due to their facile handling and air moisture stability replacing conventional expensive noble metal based catalytic systems. Amongst the non‐noble metals, copper based catalytic systems due to the variable oxidation states have been effectively used as the tunable and multifunctional catalytic materials for the promotion of selective organic transformations. These copper based catalytic systems effectively promote multifarious organic transformations promoting functionalization of the easily available organic substrates. Nitriles are a significant class of nitrogen‐containing compounds finding applications in pharmaceutical and fine chemical industries. Several organic and inorganic cyanide sources have been effectively usedto cyanate organic compounds by using multi‐ferrous copper catalysts. Furthermore, nitrile compounds are key components used for the synthesis of drug molecules and fabrication of functionalized materials.

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Section: Organic Cyanide Sourcementioning

confidence: 99%

“…The catalytic material gave an excellent catalytic performance for a broad range of functional groups attached to the aromatic ring system (See Figure 65). [43] …”

Section: Organic Cyanide Sourcementioning

confidence: 99%

Copper Mediated Chemo‐ and Stereoselective Cyanation Reactions

et al. 2021

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“…In this regard, the direct use of metal/silyl cyanides or the in situ generation of cyanide ion is often involved (Fig. 1a, b : K 4 [Fe(CN) 6 ] 8 – 14 , K 3 [Fe(CN) 6 ] 15 , ethyl cyanoacetate 16 , 17 , acetone cyanohydrin 18 – 20 , butyronitrile 21 , 4-cyanopyridine N -oxide 22 , formamide 23 , DMF/NH 4 + 24 – 26 , etc). These reactions proceed through Rosenmund-von Braun reaction mechanism and suffer from limited catalytic efficiency and/or substrate scope due to strong coordination ability and poisoning of cyanide ion.…”

Section: Introductionmentioning

confidence: 99%

Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species

et al. 2020

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Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO 2 /NH 3 as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive CC coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotopelabeled) drugs.

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“…Aryl nitriles are important key constituents of pharmaceuticals, agrochemicals, dyes, and natural products . The successful examples for the synthesis of benzonitriles were reported using superstoichiometric amount of toxic cyanide sources under harsh reaction conditions . Among cyanide sources, K 4 [Fe (CN) 6 ] is attractive candidate in synthetic chemists as non‐toxic cyano source .…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of Pd/MnO₂ nanocomposite using Solanum melongena plant extract and its application for the one‐pot synthesis of 5‐substituted 1H‐tetrazoles from aryl halides

Nasrollahzadeh

Ghorbannezhad

Sajadi

2018

Applied Organom Chemis

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In this work, for the first time, Solanum melongena plant extract was used for the green synthesis of Pd/MnO 2 nanocomposite via reduction osf Pd(II) ions to Pd(0) and their immobilization on the surface of manganese dioxide (MnO 2 ) nanoparticles (NPs) as an effective support. The synthesized nanocomposite were characterized by various analytical techniques such as Fourier transform infrared (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), field emission scanning electron microscopy (FESEM), energy dispersive X-ray spectroscopy (EDS) and UV-Vis spectroscopy. The catalytic activity of Pd/MnO 2 nanocomposite was used as a heterogeneous catalyst for the one-pot synthesis of 5-substituted 1H-tetrazoles from aryl halides containing various electron-donating or electron-withdrawing groups in the presence of K 4 [Fe (CN) 6 ] as non-toxic cyanide source and sodium azide. The products were obtained in good yields via a simple methodology and easy work-up. The nanocatalyst can be recycled and reused several times with no remarkable loss of activity. Highlights:• Green synthesis of Pd/MnO 2 nanocomposite using Solanum melongena extract.• Pd/MnO 2 nanocomposite was characterized by FT-IR, XRD, FESEM, EDS and TEM.• One-pot synthesis of 5-substituted 1H-tetrazoles from aryl halides using Pd/MnO 2 nanocomposite.• The catalyst can be easily recycled and reused several times without sensible loss in its catalytic efficiency.

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Copper-catalyzed cyanation of aryl iodides with α-cyanoacetates via C–CN bond activation

Cited by 29 publications

References 57 publications

Copper Mediated Chemo‐ and Stereoselective Cyanation Reactions

Copper Mediated Chemo‐ and Stereoselective Cyanation Reactions

Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species

Biosynthesis of Pd/MnO₂ nanocomposite using Solanum melongena plant extract and its application for the one‐pot synthesis of 5‐substituted 1H‐tetrazoles from aryl halides

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Copper-catalyzed cyanation of aryl iodides with α-cyanoacetates via C–CN bond activation

Cited by 29 publications

References 57 publications

Copper Mediated Chemo‐ and Stereoselective Cyanation Reactions

Copper Mediated Chemo‐ and Stereoselective Cyanation Reactions

Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species

Biosynthesis of Pd/MnO2 nanocomposite using Solanum melongena plant extract and its application for the one‐pot synthesis of 5‐substituted 1H‐tetrazoles from aryl halides

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Biosynthesis of Pd/MnO₂ nanocomposite using Solanum melongena plant extract and its application for the one‐pot synthesis of 5‐substituted 1H‐tetrazoles from aryl halides