Metal-mediated and metal-catalyzed hydrolysis of nitriles

Kukushkin, Vadim Yu.; Pombeiro, Armando J. L.

doi:10.1016/j.ica.2004.04.029

Cited by 396 publications

(229 citation statements)

References 163 publications

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“…The conversion of nitriles into amides by conventional acid/base strategies usually requires harsh conditions and remains impractical for most purposes due to yield and selectivity issues, since these classical methods are frequently unable to control the over-hydrolysis of the primary amide product [7,8]. The use of transition metal complexes (mainly of as catalysts under neutral and mild conditions has allowed researchers to overcome these traditional barriers, and a large number of selective catalysts for the nitrile hydration process have seen the light during the last two decades [9][10][11][12][13][14][15]. Among them, the commercially available hydride-platinum(II) complex [PtH{(PMe2O)2H}(PMe2OH)] (1), first described by Ghaffar and Parkins in 1995 [16,17], has achieved great success among organic chemists because of its outstanding activity and selectivity and its exquisite compatibility with other functional groups ( Figure 1).…”

Section: Open Accessmentioning

confidence: 99%

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Cadierno

2015

Applied Sciences

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Abstract:The air-stable hydride-platinum(II) complex [PtH{(PMe2O)2H}(PMe2OH)], reported by Parkins and co-workers in 1995, is the most versatile catalyst currently available for the hydration of C≡N bonds. It features remarkable activity under relatively mild conditions and exceptionally high functional group compatibility, facts that have allowed the implementation of this complex in the synthesis of a large number of structurally complex, biologically active molecules and natural products. In this contribution, synthetic applications of the Parkins catalyst are reviewed.

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Section: Open Accessmentioning

confidence: 99%

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Cadierno

2015

Applied Sciences

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“…Imd does not react with uncomplexed RCN species under these reaction conditions, which provides evidence that the observed double coupling is Pt II -mediated and the promoting effect of the metal is rationalized by the activation of the NCR ligands toward nucleophilic attack [33,47,48] by Imd and also by the stabilization of the formed PANT species by the chelation.…”

Section: Resultsmentioning

confidence: 74%

Platinum(II)‐Mediated Double Coupling of 2,3‐Diphenylmaleimidine with Nitrile Functionalities To Give Annulated Pentaazanonatetraenate (PANT) Systems

et al. 2016

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“…It has been known that the nitrile groups (-C≡N) in SAN are capable of coordinating to various transition metal ions. [25][26][27][28][29] When Cr(VI) is electrochemically reduced at the electrode surface, -C≡N can interact with Cr(III) in the ways of (I) terminal (end-on) σ-bonded or (II) π-bonded (side-on). 28,29 We suggest that ASV of Cr(VI) may well be facilitated at the Graphite-SAN composite electrode, due to a strong interaction between the reduced Cr(III) and -C≡N groups.…”

Section: Swasv Of Cr(vi) At a Graphite-san Composite Electrodementioning

confidence: 99%

Anodic Stripping Voltammetry for the Determination of Trace Cr(VI) with Graphite/Styrene-Acrylonitrile Copolymer Composite Electrodes

et al. 2017

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Although the addition of complexing agents is not necessary for ASV determination, so far only a few studies have been reported, probably due to the poor sensitivity and precision. Nevertheless, the oxidative stripping peak of Cr(VI) located in a more positive potential region that has much less interference by some heavy 2017 © The Japan Society for Analytical Chemistry † To whom correspondence should be addressed. A square-wave anodic stripping voltammetry (SWASV) for the determination of trace amounts of hexavalent chromium Cr(VI) at a graphite/styrene-acrylonitrile (Graphite-SAN) copolymer composite electrode is described. This method involves a preconcentration step whereby the trace Cr(VI) was cathodically reduced to Cr(III) on an electrode surface in an acetate buffer (pH 5), followed by an anodic stripping technique with a square-wave voltammetric mode. It has been shown that the analytical sensitivity is significantly improved at the Graphite-SAN copolymer composite electrode in comparison with the conventional glassy carbon electrode, due to the strong interaction between Cr(III) and the nitrile end group of the SAN copolymer. The SWASV response was characterized with respect to the pH, deposition potential, possible interferences, etc. Under the optimal conditions, the stripping peak height linearly increased with the concentration of Cr(VI) in a range from 0 to 150 ng mL -1 with a correlation coefficient of 0.997, and a detection limit of 4.2 ng mL -1was achieved based on signal-to-noise ratio of about 3. The Graphite-SAN composite electrode exhibited some interesting advantages, such as high mechanical rigid, easy surface renewable, higher sensitivity and better peak resolution in comparison with the results at conventional glassy carbon electrodes. They have been applied to the determination of Cr(VI) in real water samples with satisfactory recoveries.

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Metal-mediated and metal-catalyzed hydrolysis of nitriles

Cited by 396 publications

References 163 publications

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Synthetic Applications of the Parkins Nitrile Hydration Catalyst [PtH{(PMe2O)2H}(PMe2OH)]: A Review

Platinum(II)‐Mediated Double Coupling of 2,3‐Diphenylmaleimidine with Nitrile Functionalities To Give Annulated Pentaazanonatetraenate (PANT) Systems

Anodic Stripping Voltammetry for the Determination of Trace Cr(VI) with Graphite/Styrene-Acrylonitrile Copolymer Composite Electrodes

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