Cyanation Of Aryl Halides Research Articles

Development of Pd/C-Catalyzed Cyanation of Aryl Halides

A practical method for palladium-catalyzed cyanation of aryl halides using Pd/C is described. The new method can be applied to a variety of aryl bromide and active aryl chloride substrates to effect efficient conversions. The process features many advantages over existing cyanation conditions and the practical utility of the process has been demonstrated on scale.

An efficient palladium catalytic system for microwave assisted cyanation of aryl halides

Application of a new catalytic system for cyanation reaction of various aryl halides using K 4[Fe(CN) 6] as cyanating source was examined. The reactions were performed under microwave irradiation and results showed that application of this catalytic system and DMF at 130 °C minimized the reaction times from hours to minutes in good to excellent yields.

Highly efficient recyclable heterogeneous palladium catalyst for C–C coupling, amination and cyanation reactions

An inexpensive, air–moisture stable and reusable PS–Pd(II)–anthra complex was synthesized by reacting chloro-methylated polystyrene with anthranilic acid to get polymer anchored ligand which was then reacted with PdCl 2 to get polymer anchored complex. This complex was characterized by different spectroscopic and elemental analyses. The activity of the Pd-complex as catalyst was tested for the Suzuki, Heck, Sonogashira cross-coupling and also for amination and cyanation reactions under various conditions. The catalyst exhibits high catalytic activities for the coupling of various aryl halides with organoboronic acid, alkene, alkyne and amine along with the cyanation of aryl halides providing excellent yields of desired product. Further, the catalyst can be easily recovered quantitatively by simple filtration and reused up to five times without sufficient loss of its catalytic activity.

ChemInform Abstract: Ligand‐Free CuI‐Catalyzed Cyanation of Aryl Halides Using K4[Fe(CN)6] as Cyanide Source and Water as Solvent.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Corrigendum to “Microwave-enhanced and ligand-free copper-catalyzed cyanation of aryl halides with K4[Fe(CN)6] in water” [Tetrahedron Lett. 50 (2009) 4595–4597

Corrigendum to “Microwave-enhanced and ligand-free copper-catalyzed cyanation of aryl halides with K4[Fe(CN)6] in water” [Tetrahedron Lett. 50 (2009) 4595–4597

Ligand-free CuI-catalyzed cyanation of aryl halides using K 4[Fe(CN) 6] as cyanide source and water as solvent

A methodology for the cyanation of aryl iodides is reported using copper iodide as the catalyst, K 4[Fe(CN) 6] as the cyanide source, and small quantities of water and tetraethylene glycol as the solvent. Reactions are complete within 30 min of microwave heating at 175 °C. A simple work-up procedure has also been devised.

ChemInform Abstract: Microwave‐Enhanced and Ligand‐Free Copper‐Catalyzed Cyanation of Aryl Halides with K4[Fe(CN)6] in Water.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Ligand-Free Cu-Catalyzed Cyanation of Aryl Halides with K4[Fe(CN)6] in Water

A simple methodology for Cu-catalyzed cyanation of aryl halides with K4[Fe(CN)6] was developed with water as the solvent in conjunction with ligand-free Cu(OAc)2·H2O as the catalyst. The suggested methodology is applicable to cyanation of a wide range of aryl iodides and activated aryl bromides, and allows the catalyst to be reused six times with a very slight change in the catalytic activity. Keywords: Cyanation, aryl halide, ligand-free catalyst, water solvent

Microwave-enhanced and ligand-free copper-catalyzed cyanation of aryl halides with K 4[Fe(CN) 6] in water

Copper-catalyzed cyanation of aryl halides was improved to be more economical and environmentally friendly by using water as the solvent and ligand-free Cu(OAc) 2·H 2O as the catalyst under microwave heating. The suggested methodology was applicable to a wide range of substrates including aryl iodides and activated aryl bromides.

Development of an Open-Air and Robust Method for Large-Scale Palladium-Catalyzed Cyanation of Aryl Halides: The Use of i-PrOH to Prevent Catalyst Poisoning by Oxygen

Palladium-catalyzed cyanation of aryl halides is an often capricious reaction and lacks robustness due to catalyst poisoning by oxygen. In this report, an open-air and robust method for large-scale cyanation was developed and the use of commercially available i-propanol as an additive was critical for achieving the open-air, robust and scaleable process. Under the protection by i-propanol, the catalyst life was significantly prolonged.

Ethylenediamine/Cu(OAc)2· H2O-catalyzed cyanation of aryl halides with K4[Fe(CN)6

Commercially available and inexpensive ethylenediamine/Cu(OAc) 2 · H 2 O has been found to be a highly effective catalyst system for the cyanation of aryl bromides in the solvent of NMP. At the same time, the highly activated aryl chlorides with NO 2 groups gave corresponding benzonitriles in good yields. Similar to the previous observation, it is not necessary to use an excess of K 4 [Fe(CN) 6 ] in the cyanation reaction (only 20 mol% of K 4 [Fe(CN) 6 ] was used). In other hand, a more remarkable KI-accelerated effect was observed for the cyanation reaction: the addition of KI increased the yield from 6% to 91% in the cyanation of bromobenzene.

ChemInform Abstract: Palladium‐Catalyzed Cyanation of Aryl Halides Using K4[Fe(CN)6] as Cyanide Source, Water as Solvent, and Microwave Heating.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A Bio-inspired Copper Catalyst System for Practical Catalytic Cyanation of Aryl Bromides

A general and environmentally improved protocol for the cyanation of aryl halides with the nontoxic cyanide source potassium hexacyanoferrate(II) (K 4 [Fe(CN) 6 ]) using copper catalysis and a ligand system based on l-alkyl-1H -imidazoles is presented. The advantages of this system are a wide substrate range, high selectivity, easy handling, and inexpensive reagents.

Pd/C‐Catalyzed Cyanation of Aryl Halides in Aqueous PEG

AbstractAn environmentally friendly Pd/C–PEG–H2O system was developed for the cyanation of aryl halides under microwave irradiation. A wide range of aryl bromides, iodides, and some activated chlorides were demonstrated to be cyanated smoothly by using nontoxic K4[Fe(CN)6]·3H2O as the cyanide source. There is no phosphorus‐ or nitrogen‐containing ligand or solvent involved. Moreover, this reaction can becarried out without the protection of inert atmosphere. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

Palladium-catalyzed cyanation of aryl halides using K 4[Fe(CN) 6] as cyanide source, water as solvent, and microwave heating

A methodology for the cyanation of aryl iodides and activated aryl bromides is reported using water as the solvent and K 4[Fe(CN) 6] as the cyanide source. Reactions are complete within 20 min.

Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate) catalyzed Suzuki, Heck, Sonogashira, and cyanation reactions

Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate): a structurally well-defined O-containing transition metal complex is reported as an efficient catalyst for Suzuki, Heck, and Sonogashira cross-coupling reactions. The protocol was also applied successfully for cyanation of aryl halides under milder operating conditions. The system tolerated the coupling of various aryl halides with alkenes, alkynes, and organoboronic acid along with the cyanation of aryl halides providing good to excellent yields of desired products.

ChemInform Abstract: Pd/C: A Recyclable Catalyst for Cyanation of Aryl Halides with K4[Fe(CN)6

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Pd/C: A Recyclable Catalyst for Cyanation of Aryl Halides with K4[Fe(CN)6

Aryl nitriles have been prepared from the corresponding aryl halides with potassium hexacyanoferrate(II) using Pd/C as a catalyst. No ligand or cocatalyst is required. This protocol also avoids the use of highly toxic alkali cyanides. Furthermore, the catalyst can be recycled via simple filtration and washing sequences.

A State‐of‐the‐Art Cyanation of Aryl Bromides: A Novel and Versatile Copper Catalyst System Inspired by Nature

A general protocol for the cyanation of aryl halides with the nontoxic cyanide source K4[Fe(CN)6] using copper catalysis and a ligand system based on 1-alkylimidazoles is presented. The advantages of this system are the high selectivity, a unique substrate range, easy handling, and inexpensive reagents.

Palladium-Catalyzed, Copper(I)-Mediated Coupling of Boronic Acids and Benzylthiocyanate. A Cyanide-Free Cyanation of Boronic Acids

A new method for the synthesis of nitriles is described. As a complement to the classic cyanation of aryl halides using cyanide sources and a transition metal catalyst, the palladium-catalyzed cross-coupling of thiocyanates with boronic acids in the presence of copper(I) thiophene-2-carboxylate (CuTC) affords nitriles in good to excellent yields.