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Journal articles on the topic 'Nitriles. Catalysis'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Robertson, Dan E., Jennifer A. Chaplin, Grace DeSantis, Mircea Podar, Mark Madden, Ellen Chi, Toby Richardson, et al. "Exploring Nitrilase Sequence Space for Enantioselective Catalysis." Applied and Environmental Microbiology 70, no. 4 (April 2004): 2429–36. http://dx.doi.org/10.1128/aem.70.4.2429-2436.2004.

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ABSTRACT Nitrilases are important in the biosphere as participants in synthesis and degradation pathways for naturally occurring, as well as xenobiotically derived, nitriles. Because of their inherent enantioselectivity, nitrilases are also attractive as mild, selective catalysts for setting chiral centers in fine chemical synthesis. Unfortunately, <20 nitrilases have been reported in the scientific and patent literature, and because of stability or specificity shortcomings, their utility has been largely unrealized. In this study, 137 unique nitrilases, discovered from screening of >600 biotope-specific environmental DNA (eDNA) libraries, were characterized. Using culture-independent means, phylogenetically diverse genomes were captured from entire biotopes, and their genes were expressed heterologously in a common cloning host. Nitrilase genes were targeted in a selection-based expression assay of clonal populations numbering 106 to 1010 members per eDNA library. A phylogenetic analysis of the novel sequences discovered revealed the presence of at least five major sequence clades within the nitrilase subfamily. Using three nitrile substrates targeted for their potential in chiral pharmaceutical synthesis, the enzymes were characterized for substrate specificity and stereospecificity. A number of important correlations were found between sequence clades and the selective properties of these nitrilases. These enzymes, discovered using a high-throughput, culture-independent method, provide a catalytic toolbox for enantiospecific synthesis of a variety of carboxylic acid derivatives, as well as an intriguing library for evolutionary and structural analyses.

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2

Lévay, Krisztina, and László Hegedűs. "Recent Achievements in the Hydrogenation of Nitriles Catalyzed by Transitional Metals." Current Organic Chemistry 23, no. 18 (November 26, 2019): 1881–900. http://dx.doi.org/10.2174/1385272823666191007160341.

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Amines are important and valuable intermediates in the pharmaceutical, plastic and agrochemical industry. Hence, there is an increasing interest in developing improved process for the synthesis of amines. The heterogeneous catalytic hydrogenation of nitriles is one of the most frequently applied methods for the synthesis of diverse amines, but the homogeneous catalysis has also received a growing attention from the catalysis community. This mini-review provides an overview of the recent achievements in the selective reduction of nitriles using both homogeneous and heterogeneous transition metal catalysts.

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3

Lee, S. G., J. Kim, and J. Bouffard. "Tandem Divergent Catalysis using Nitriles." Synfacts 10, no. 12 (November 18, 2014): 1347. http://dx.doi.org/10.1055/s-0034-1379609.

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4

Ren, Yun-Lai, Jianji Wang, Xinzhe Tian, Fangping Ren, Xinqiang Cheng, and Shuang Zhao. "Direct Conversion of Benzyl Ethers into Aryl Nitriles." Synlett 29, no. 18 (October 16, 2018): 2444–48. http://dx.doi.org/10.1055/s-0037-1611062.

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A direct method was developed for the conversion of benzyl ethers into aryl nitriles by using NH4OAc as the nitrogen source and oxygen as the terminal oxidant with catalysis by TEMPO/HNO3; the method is valuable for both the synthesis of aromatic nitriles and for the deprotection of ether-protected hydroxy groups to form nitrile groups in multistep organic syntheses.

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5

Naeimi, Hossein, and Mohsen Moradian. "Metal(II) Schiff base complexes as catalysts for the high-regioselective conversion of epoxides to β-hydroxy nitriles in glycol solvents." Canadian Journal of Chemistry 84, no. 11 (November 1, 2006): 1575–79. http://dx.doi.org/10.1139/v06-158.

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A facile preparation of 3-hydroxy propanenitrile derivatives is described involving ring opening of epoxides with potassium cyanide in glycol solvents in the presence of Schiff base complexes as catalysts. This method occurs under neutral and mild conditions with high yields and high regioselectivity. Thus, several β-Hydroxy nitriles, useful intermediates toward biologically-active molecules, are easily obtained at room temperature.Key words: β-hydroxy nitrile, Schiff base, epoxide, glycol, catalyst.

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6

Zhao, Zhao Hui, Han Bo Zou, and Wei Ming Lin. "Influence of Final Nitriding Temperature on the Preparation and the Catalytic Performance of CoMoN_x/CNTs for Ammonia Decomposition." Advanced Materials Research 557-559 (July 2012): 1514–17. http://dx.doi.org/10.4028/www.scientific.net/amr.557-559.1514.

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A series of cobalt-molybdenum nitride catalysts were prepared using Co-Mo oxide precursors via temperature-programmed reaction in N2-H2 mixed gases. The catalysts were characterized by N2 physical adsorption, X-ray diffraction, temperature-programmed desorption of H2. Their catalytic performance was evaluated in the model reaction of ammonia decomposition. The influence of the final nitriding temperatures on the surface properties and the catalytic perfomance of CoMoNx/CNTs were described. The catalyst nitrided at 650°C shows the best catalytic performance. The results indicated that a suitable final nitriding temperature contributes directly to the formation of nitrides and favor the catalyst activity.

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7

Watson, Geert, Parviz Gohari Derakhshandeh, Sara Abednatanzi, Johannes Schmidt, Karen Leus, and Pascal Van Der Voort. "A Ru-Complex Tethered to a N-Rich Covalent Triazine Framework for Tandem Aerobic Oxidation-Knoevenagel Condensation Reactions." Molecules 26, no. 4 (February 5, 2021): 838. http://dx.doi.org/10.3390/molecules26040838.

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Herein, a highly N-rich covalent triazine framework (CTF) is applied as support for a RuIII complex. The bipyridine sites within the CTF provide excellent anchoring points for the [Ru(acac)2(CH3CN)2]PF6 complex. The obtained robust RuIII@bipy-CTF material was applied for the selective tandem aerobic oxidation-Knoevenagel condensation reaction. The presented system shows a high catalytic performance (>80% conversion of alcohols to α, β-unsaturated nitriles) without the use of expensive noble metals. The bipy-CTF not only acts as the catalyst support but also provides the active sites for both aerobic oxidation and Knoevenagel condensation reactions. This work highlights a new perspective for the development of highly efficient and robust heterogeneous catalysts applying CTFs for cascade catalysis.

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8

Marquez, Carlos, Matthieu Corbet, Simon Smolders, Philippe Marion, and Dirk De Vos. "Double metal cyanides as heterogeneous Lewis acid catalysts for nitrile synthesis via acid-nitrile exchange reactions." Chemical Communications 55, no. 86 (2019): 12984–87. http://dx.doi.org/10.1039/c9cc05382d.

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9

Leadbeater, Nicholas, Jyoti Nandi, and Mason Witko. "Combining Oxoammonium Cation Mediated Oxidation and Photoredox Catalysis for the Conversion of Aldehydes into Nitriles." Synlett 29, no. 16 (September 12, 2018): 2185–90. http://dx.doi.org/10.1055/s-0037-1610272.

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A method to oxidize aromatic aldehydes to nitriles has been developed. It involves a dual catalytic system of 4-acetamido-TEMPO and visible-light photoredox catalysis. The reaction is performed using ammonium persulfate as both the terminal oxidant and nitrogen source.

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10

Jiang, Shuai-Shuai, Yan-Chen Wu, Shu-Zheng Luo, Fan Teng, Ren-Jie Song, Ye-Xiang Xie, and Jin-Heng Li. "Silver-mediated oxidative 1,2-alkylesterification of styrenes with nitriles and acids via C(sp3)–H functionalization." Chemical Communications 55, no. 85 (2019): 12805–8. http://dx.doi.org/10.1039/c9cc06437k.

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A new silver-mediated 1,2-alkylesterification of alkenes with nitriles and acids promoted by a catalytic amount of nickel catalyst for producing acyloxylated nitriles has been developed via a C(sp³)–H functionalization process.

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11

Vagkidis, Nikolaos, Alexander J. Brown, and Paul A. Clarke. "Evaluation of Amino Nitriles and an Amino Imidate as Organocatalysts in Aldol Reactions." Synthesis 51, no. 21 (August 8, 2019): 4106–12. http://dx.doi.org/10.1055/s-0039-1690150.

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The efficiency of l-valine and l-proline nitriles and a tert-butyl l-proline imidate as organocatalysts for the aldol reaction have been evaluated. l-Valine nitrile was found to be a syn-selective catalyst, while l-proline nitrile was found to be anti-selective, and gave products in modest to good enantioselectivities. tert-Butyl l-proline imidate was found to be a very efficient catalyst in terms of conversion of starting reagents to products, and gave good anti-selectivity. The enantioselectivity of the tert-butyl l-proline imidate was found to be good to excellent, with products being formed in up to 94% enantiomeric excess.

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12

Cho, Jin Hee, Sangmoon Byun, Ahra Cho, and B. Moon Kim. "One-pot, chemoselective synthesis of secondary amines from aryl nitriles using a PdPt–Fe3O4 nanoparticle catalyst." Catalysis Science & Technology 10, no. 13 (2020): 4201–9. http://dx.doi.org/10.1039/d0cy00630k.

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We have developed a new catalytic method for the one-pot, cascade synthesis of unsymmetrical secondary amines via the reductive amination of aryl nitriles with nitroalkanes using a PdPt–Fe₃O₄ nanoparticle (NP) catalyst.

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13

Stuart, John G., and Kenneth M. Nicholas. "Cobalt-Mediated Synthesis of Propargyl Nitriles and α-Alkoxy Propargyl Nitriles." Synthesis 1989, no. 06 (1989): 454–55. http://dx.doi.org/10.1055/s-1989-27287.

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14

Rucká, Lenka, Martin Chmátal, Natalia Kulik, Lucie Petrásková, Helena Pelantová, Petr Novotný, Romana Příhodová, Miroslav Pátek, and Ludmila Martínková. "Genetic and Functional Diversity of Nitrilases in Agaricomycotina." International Journal of Molecular Sciences 20, no. 23 (November 28, 2019): 5990. http://dx.doi.org/10.3390/ijms20235990.

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Nitrilases participate in the nitrile metabolism in microbes and plants. They are widely used to produce carboxylic acids from nitriles. Nitrilases were described in bacteria, Ascomycota and plants. However, they remain unexplored in Basidiomycota. Yet more than 200 putative nitrilases are found in this division via GenBank. The majority of them occur in the subdivision Agaricomycotina. In this work, we analyzed their sequences and classified them into phylogenetic clades. Members of clade 1 (61 proteins) and 2 (25 proteins) are similar to plant nitrilases and nitrilases from Ascomycota, respectively, with sequence identities of around 50%. The searches also identified five putative cyanide hydratases (CynHs). Representatives of clade 1 and 2 (NitTv1 from Trametes versicolor and NitAg from Armillaria gallica, respectively) and a putative CynH (NitSh from Stereum hirsutum) were overproduced in Escherichia coli. The substrates of NitTv1 were fumaronitrile, 3-phenylpropionitrile, β-cyano-l-alanine and 4-cyanopyridine, and those of NitSh were hydrogen cyanide (HCN), 2-cyanopyridine, fumaronitrile and benzonitrile. NitAg only exhibited activities for HCN and fumaronitrile. The substrate specificities of these nitrilases were largely in accordance with substrate docking in their homology models. The phylogenetic distribution of each type of nitrilase was determined for the first time.

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15

Riley, Darren, and Nicole Neyt. "Approaches for Performing Reductions under Continuous-Flow Conditions." Synthesis 50, no. 14 (June 18, 2018): 2707–20. http://dx.doi.org/10.1055/s-0037-1610153.

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A concise overview of approaches to perform reductions of various functionalities including aldehydes, ketones, esters, imines, nitriles, nitro groups, alkenes and alkynes under continuous-flow conditions are highlighted and discussed in this short review.1 Introduction2 Reduction of Aldehydes, Ketones and Esters3 Reduction of Imines and Nitriles4 Reduction of Nitro Groups5 Reduction of Alkenes6 Partial Reduction of Alkynes7 Conclusion

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16

Selvam, Nagarajan Panneer, Sundar Saranya, and Paramasivan T. Perumal. "A convenient and efficient protocol for the synthesis of symmetrical N,N′-alkylidine bisamides by sulfamic acid under solvent-free conditions." Canadian Journal of Chemistry 86, no. 1 (January 1, 2008): 32–38. http://dx.doi.org/10.1139/v07-134.

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A simple and convenient approach to the synthesis of symmetrical N,N′-alkylidine bisamides is described. Aromatic and aliphatic nitriles react with aromatic aldehydes in the presence of sulfamic acid to give the corresponding bisamides in moderate yields.Key words: alkylidine bisamides, nitrile, sulfamic acid.

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17

Nandi, Jyoti, and Nicholas E. Leadbeater. "Visible-light-driven catalytic oxidation of aldehydes and alcohols to nitriles by 4-acetamido-TEMPO using ammonium carbamate as a nitrogen source." Organic & Biomolecular Chemistry 17, no. 41 (2019): 9182–86. http://dx.doi.org/10.1039/c9ob01918a.

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A mild and efficient route to prepare nitriles from aldehydes by combining photoredox catalysis with oxoammonium cations is reported. The methodology is also extended to the one-pot two-step conversion of alcohols to nitriles.

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18

Svoboda, Jiří, Zuzana Kocfeldová, and Jaroslav Paleček. "Reaction of 4-substituted benzaldehydes and acetophenones with chloroacetonitrile." Collection of Czechoslovak Chemical Communications 53, no. 4 (1988): 822–32. http://dx.doi.org/10.1135/cccc19880822.

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Under conditions of phase-transfer catalysis or in homogeneous solution of potassium tert-butoxide the title compounds give stereoisomeric mixtures of substituted 2,3-epoxy nitriles III and IV. Alkaline hydrolysis of epoxy nitriles IV afforded the corresponding 2-arylpropanals in low yields. On treatment with methanol and potassium carbonate, epoxy nitriles III and IV were converted into epoxy esters in good yields.

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19

Martínková, Ludmila, Norbert Klempier, Margit Preiml, Mária Ovesná, Marek Kuzma, Veronika Mylerová, and Vladimír Kren. "Selective biotransformation of substituted alicyclic nitriles by Rhodococcus equi A4." Canadian Journal of Chemistry 80, no. 6 (June 1, 2002): 724–27. http://dx.doi.org/10.1139/v01-205.

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Nitrile hydratase from Rhodococcus equi A4 discriminated between geometric isomers of substituted alicyclic nitriles. The enzyme transformed trans-4-benzoyloxycyclohexanecarbonitrile (trans-1a), cis-3-benzoyloxy cyclohexanecarbonitrile (cis-2a), trans-2-hydroxycyclohexanecarbonitrile (trans-3a), and trans-2-hydroxycyclo pentanecarbonitrile (trans-4a) into the corresponding amides. On the contrary, cis-2-hydroxycyclohexanecarbonitrile (cis-3a) and cis-2-hydroxycyclopentanecarbonitrile (cis-4a) were not converted to a significant extent. cis-4-Ben zoyl oxycyclohexanecarbonitrile (cis-1a) was also a substrate of the enzyme but reacted slowly. Diequatorial arrangement of the substituents in trans-1a, cis-2a, and trans-3a appears to positively influence the activity of the nitrile hydratase.

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20

Gour-Salin, Barbara J., Paule Lachance, and Andrew C. Storer. "Inhibition of papain by peptide nitriles: conversion of the nitrile group into other functionalities via the papain:nitrile thioimidate ester adduct." Canadian Journal of Chemistry 69, no. 8 (August 1, 1991): 1288–97. http://dx.doi.org/10.1139/v91-192.

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Peptide nitriles are reversible inhibitors of papain that form thioimidates with the cysteine thiol in the enzyme's active site. These thioimidates undergo reactions with thiols and amines to form acids and amidines, respectively. These reactions were also found to be stereospecific. Only a thioimidate derived from an L-amino acid nitrile will react with exogenous nucleophiles. These reactions were followed by 13C and 15N NMR techniques. Key words: papain, nitrile, l3C NMR, 15N NMR, thioimidate.

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21

Hota, Pradip Kumar, Subir Maji, Jasimuddin Ahmed, N. M. Rajendran, and Swadhin K. Mandal. "NHC-catalyzed silylative dehydration of primary amides to nitriles at room temperature." Chemical Communications 56, no. 4 (2020): 575–78. http://dx.doi.org/10.1039/c9cc08413d.

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22

Naruto, Hiroki, and Hideo Togo. "Preparation of 2-Arylquinolines from 2-Arylethyl Bromides and Aromatic Nitriles with Magnesium and N-Iodosuccinimide." Synthesis 52, no. 07 (January 23, 2020): 1122–30. http://dx.doi.org/10.1055/s-0039-1691642.

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Treatment of 2-arylethylmagnesium bromides, prepared from 2-arylethyl bromides and magnesium, with aromatic nitriles, followed by reaction with water and then with N-iodosuccinimide under irradiation with a tungsten lamp, gave the corresponding 2-arylquinolines in good to moderate yields under transition-metal-free conditions. 2-Alkylquinolines could be also obtained in moderate yields by the same procedure with 2-arylethyl bromides, magnesium, aliphatic nitriles bearing a secondary alkyl group, and N-iodosuccinimide.

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23

Borghs, Jannik C., Mai Anh Tran, Jan Sklyaruk, Magnus Rueping, and Osama El-Sepelgy. "Sustainable Alkylation of Nitriles with Alcohols by Manganese Catalysis." Journal of Organic Chemistry 84, no. 12 (May 22, 2019): 7927–35. http://dx.doi.org/10.1021/acs.joc.9b00792.

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24

Yildirim, Selcuk, Reto Ruinatscha, Rainer Gross, Roland Wohlgemuth, Hans-Peter E. Kohler, Bernard Witholt, and Andreas Schmid. "Selective hydrolysis of the nitrile group of cis-dihydrodiols from aromatic nitriles." Journal of Molecular Catalysis B: Enzymatic 38, no. 2 (February 2006): 76–83. http://dx.doi.org/10.1016/j.molcatb.2005.11.006.

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25

Barker, Graeme, Madeha R. Alshawish, Melanie C. Skilbeck, and Iain Coldham. "Remarkable Configurational Stability of Magnesiated Nitriles." Angewandte Chemie International Edition 52, no. 30 (June 19, 2013): 7700–7703. http://dx.doi.org/10.1002/anie.201303442.

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26

Fleming, Fraser F, Wang Liu, Somraj Ghosh, and Omar W Steward. "Metalated Nitriles: Internal 1,2-Asymmetric Induction." Angewandte Chemie International Edition 46, no. 37 (September 17, 2007): 7098–100. http://dx.doi.org/10.1002/anie.200701550.

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27

Tao, Chuanzhou, Bin Wang, Lei Sun, Zhou Liu, Yadong Zhai, Xiulian Zhang, and Jian Wang. "Merging visible-light photoredox and copper catalysis in catalytic aerobic oxidation of amines to nitriles." Organic & Biomolecular Chemistry 15, no. 2 (2017): 328–32. http://dx.doi.org/10.1039/c6ob02510b.

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28

Le Vaillant, Franck, Matthew D. Wodrich, and Jérôme Waser. "Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation." Chemical Science 8, no. 3 (2017): 1790–800. http://dx.doi.org/10.1039/c6sc04907a.

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29

Lambers-Verstappen, Mariëlle M H., and Johannes G de Vries. "Rhodium-Catalysed Asymmetric Hydroformylation of Unsaturated Nitriles." Advanced Synthesis & Catalysis 345, no. 4 (April 2003): 478–82. http://dx.doi.org/10.1002/adsc.200390053.

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30

Wu, Xuesong, Jan Riedel, and Vy M. Dong. "Transforming Olefins into γ ,δ -Unsaturated Nitriles through Copper Catalysis." Angewandte Chemie International Edition 56, no. 38 (August 10, 2017): 11589–93. http://dx.doi.org/10.1002/anie.201705859.

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31

Wu, Xuesong, Jan Riedel, and Vy M. Dong. "Transforming Olefins into γ ,δ -Unsaturated Nitriles through Copper Catalysis." Angewandte Chemie 129, no. 38 (August 10, 2017): 11747–51. http://dx.doi.org/10.1002/ange.201705859.

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32

Czégéni, Csilla Enikő, Sourav De, Antal Udvardy, Nóra Judit Derzsi, Gergely Papp, Gábor Papp, and Ferenc Joó. "Selective Hydration of Nitriles to Corresponding Amides in Air with Rh(I)-N-Heterocyclic Complex Catalysts." Catalysts 10, no. 1 (January 16, 2020): 125. http://dx.doi.org/10.3390/catal10010125.

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A new synthetic method for obtaining [RhCl(cod)(NHC)] complexes (1–4) (cod = η4-1,5-cyclooctadiene, NHC = N-heterocyclic carbene: IMes, SIMes, IPr, and SIPr, respectively) is reported together with the catalytic properties of 1–4 in nitrile hydration. In addition to the characterization of 1–4 in solution by 13C NMR spectroscopy, the structures of complexes 3, and 4 have been established also in the solid state with single-crystal X-ray diffraction analysis. The Rh(I)-NHC complexes displayed excellent catalytic activity in hydration of aromatic nitriles (up to TOF = 276 h−1) in water/2-propanol (1/1 v/v) mixtures in air.

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33

Zhu, Lei, Taku Kitanosono, Pengyu Xu, and Shū Kobayashi. "Chiral Cu(II)-catalyzed enantioselective β-borylation of α,β-unsaturated nitriles in water." Beilstein Journal of Organic Chemistry 11 (October 27, 2015): 2007–11. http://dx.doi.org/10.3762/bjoc.11.217.

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The promising performance of copper(II) complexes was demonstrated for asymmetric boron conjugate addition to α,β-unsaturated nitriles in water. The catalyst system, which consisted of Cu(OAc)2 and a chiral 2,2′-bipyridine ligand, enabled β-borylation and chiral induction in water. Subsequent protonation, which was accelerated in aqueous medium, led to high activity of this asymmetric catalysis. Both solid and liquid substrates were suitable despite being insoluble in water.

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34

Chiba, Shunsuke, and Derek Yiren Ong. "Controlled Reduction of Nitriles by Sodium Hydride and Zinc Chloride." Synthesis 52, no. 09 (February 19, 2020): 1369–78. http://dx.doi.org/10.1055/s-0039-1690838.

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A new protocol for the controlled reduction of nitriles to aldehydes was developed using a combination of sodium hydride and zinc chloride. The iminyl zinc intermediates derived from aromatic nitriles could be further functionalized with allylmetal nucleophiles to afford homoallylamines. As the method allows the reduction of various aliphatic and aromatic nitriles with a concise procedure under milder reaction conditions and exhibits wide functional group compatibility, it is well suited for use in various opportunities in chemical synthesis.

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35

Vejvoda, Vojtěch, Ludmila Martínková, Alicja B. Veselá, Ondřej Kaplan, Sabine Lutz-Wahl, Lutz Fischer, and Bronislava Uhnáková. "Biotransformation of nitriles to hydroxamic acids via a nitrile hydratase–amidase cascade reaction." Journal of Molecular Catalysis B: Enzymatic 71, no. 1-2 (August 2011): 51–55. http://dx.doi.org/10.1016/j.molcatb.2011.03.008.

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36

Armor, John N. "Transfer hydroge´nation with nitriles." Applied Catalysis A: General 107, no. 2 (January 1994): N19—N20. http://dx.doi.org/10.1016/0926-860x(94)85166-2.

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37

Vejvoda, Vojtěch, Ondřej Kaplan, Karel Bezouška, and Ludmila Martínková. "Mild hydrolysis of nitriles by the immobilized nitrilase from Aspergillus niger K10." Journal of Molecular Catalysis B: Enzymatic 39, no. 1-4 (May 2006): 55–58. http://dx.doi.org/10.1016/j.molcatb.2006.01.027.

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38

Winkler, Margit, Anton Glieder, and Norbert Klempier. "Enzyme stabilizer DTT catalyzes nitrilase analogue hydrolysis of nitriles." Chemical Communications, no. 12 (2006): 1298. http://dx.doi.org/10.1039/b516937b.

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39

Cao, Chengyao, Jinyu Sheng, and Chao Chen. "Cu-Catalyzed Cascade Annulation of Diaryliodonium Salts and Nitriles: Synthesis of Nitrogen-Containing Heterocycles." Synthesis 49, no. 23 (October 11, 2017): 5081–92. http://dx.doi.org/10.1055/s-0036-1589515.

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Developing versatile methodologies to construct various nitrogen-containing heterocycles is a crucially significant part of contemporary organic chemistry. This review summarizes recent developments on the formation of nitrogen-containing heterocycles triggered by diaryliodonium salts. Diaryliodonium salts, as electrophilic arylating agents in the presence of catalytic copper salts, can react with nitriles to give N-arylnitrilium cations, which are highly reactive species. These species can efficiently react with nucleophiles, including C-, N- and O-nucleophiles, to give the corresponding products. This strategy is not only efficient and convenient, but also enables the synthesis of diverse nitrogen-containing heterocycles such as quinolines, quinazolines, and phenanthridines.1 Introduction2 Strategies and Mechanisms3 Cascade Annulations3.1 Cascade Annulation of Diaryliodoniums, Nitriles and C-Nucleophiles3.2 Cascade Annulation of Diaryliodoniums, Nitriles and N-Nucleophiles3.3 Cascade Annulation of Diaryliodoniums, Nitriles and O-Nucleophiles4 Summary and Outlook

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40

Schneekönig, Jacob, Bianca Tannert, Helen Hornke, Matthias Beller, and Kathrin Junge. "Cobalt pincer complexes for catalytic reduction of nitriles to primary amines." Catalysis Science & Technology 9, no. 8 (2019): 1779–83. http://dx.doi.org/10.1039/c9cy00225a.

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41

Griffith, William P., and Maria Suriaatmaja. "Studies on transition-metal nitrido and oxo complexes. Part 20. Oxoruthenates and oxo-osmates in oxidation catalysis; cis-[Os(OH)2O4]2- as a catalytic oxidant for primary amines and for alcohols." Canadian Journal of Chemistry 79, no. 5-6 (May 1, 2001): 598–606. http://dx.doi.org/10.1139/v00-181.

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cis-[Os(OH)2O4]2 with [Fe(CN)6]3 and other co-oxidants has been studied as a catalytic reagent for the oxidative dehydrogenation of primary aromatic and aliphatic amines to nitriles, the oxidation of primary alcohols to carboxylic acids and of secondary alcohols to ketones. Electronic and Raman spectroscopy have been used to elucidate the nature of the oxoruthenates and oxo-osmates present in a number of reported organic oxidations catalyzed by ruthenium and osmium species.Key words: oxidation catalysis, ruthenium, osmium, amine dehydrogenation, alcohol oxidation.

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42

Neugebauer, Witold, Eric Pinet, Munsok Kim, and Paul R. Carey. "Modified method of synthesis of N-substituted dithioesters of amino acids and peptides in the Pinner reaction." Canadian Journal of Chemistry 74, no. 3 (March 1, 1996): 341–43. http://dx.doi.org/10.1139/v96-038.

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An improved method for the synthesis of dithioesters of amino acids and peptides has been developed. The syntheses have been carried out from the nitriles. The addition of thiol to the nitrile derivative in the Pinner step of dithioester synthesis was activated with hydrogen fluoride. A few examples of dithioester synthesis using liquid HF are described. Some novel dithioesters, which are model compounds for resonance Raman spectroscopic studies of dithioacylpapain intermediates, are described. Key words: dithioesters, amino acids, Pinner reaction, HF, isotopes.

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43

Liguori, Angelo, Giovanni Sindona, Giovanni Romeo, and Nicola Uccella. "Direct Conversion of Hydroxamic Acids into Nitriles." Synthesis 1987, no. 02 (1987): 168. http://dx.doi.org/10.1055/s-1987-27874.

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44

Pearson-Long, Morwenna, Philippe Bertus, Julien Caillé, Mathilde Pantin, and Fabien Boeda. "Zinc-Mediated Double Addition on Functionalized Nitriles." Synthesis 51, no. 06 (January 24, 2019): 1329–41. http://dx.doi.org/10.1055/s-0037-1611704.

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Allylzinc reagents were used to access highly functionalized tertiary carbinamine derivatives in high yields from cyanoesters and cyanocarbonates. While the monoaddition of organometallics on nitriles is generally observed, in this work the nucleophilic allylation occurs twice, due to an intermediate transfer of the carbonyl moiety onto the nitrogen atom. The chemoselectivity of the reaction allows the presence of various functionalities and in the case of carbonate derivatives, the nature of the final product was modulated by kinetic control, giving selectively hydroxyamides or cyclic carbamates.

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45

Meshram, H. M. "Dehydration of Aldoximes to Nitriles with Clay." Synthesis 1992, no. 10 (1992): 943–44. http://dx.doi.org/10.1055/s-1992-26271.

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46

Chin, Chong Shik, and Byeongno Lee. "Hydrogenation of nitriles with iridium-triphenylphosphine complexes." Catalysis Letters 14, no. 1 (1992): 135–40. http://dx.doi.org/10.1007/bf00764228.

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47

Wang, Mei-Xiang. "Enantioselective Biotransformations of Nitriles in Organic Synthesis." Topics in Catalysis 35, no. 1-2 (June 2005): 117–30. http://dx.doi.org/10.1007/s11244-005-3817-1.

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48

Muchall, Heidi M., and Nick H. Werstiuk. "Ionization potentials of nitriles — Photoelectron spectra of succinonitrile and glutaronitrile." Canadian Journal of Chemistry 84, no. 9 (September 1, 2006): 1124–31. http://dx.doi.org/10.1139/v06-141.

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The He(I) photoelectron spectra of succinonitrile (1) and glutaronitrile (2), both with extensive overlap of ionization bands in the low-energy region, are reported. To assign ionizations, we studied the conformational behaviour and resulting ionization energy dependence of 1 and 2 computationally with the B3LYP/6-31+G(d) model chemistry based on the fact that it reliably reproduces the ionization potentials of eleven mono- and di-nitriles, both saturated and unsaturated. The correlation of proton affinities with observed ionization potentials of 1, 2, and malononitrile establishes the orbital sequence of four C≡N π orbitals followed by two nitrogen lone pair orbitals as the highest occupied molecular orbitals for all three compounds.Key words: photoelectron spectrum, ionization potential, conformational dependence, nitrile, DFT.

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49

Goodman, Jonathan T., and Thomas B. Rauchfuss. "Addition of Nitriles to Metal Sulfides: Possible Insight into the Metal Sulfide Catalyzed Hydrogenation of Nitriles and Dinitrogen." Angewandte Chemie International Edition in English 36, no. 19 (October 17, 1997): 2083–85. http://dx.doi.org/10.1002/anie.199720831.

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50

Guo, Beibei, Johannes G. de Vries, and Edwin Otten. "Hydration of nitriles using a metal–ligand cooperative ruthenium pincer catalyst." Chemical Science 10, no. 45 (2019): 10647–52. http://dx.doi.org/10.1039/c9sc04624k.

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