Improving palladium-catalyzed cyanation of aryl halides: development of a state-of-the-art methodology using potassium hexacyanoferrate(II) as cyanating agent

Schareina, Thomas; Zapf, Alexander; Beller, Matthias

doi:10.1016/j.jorganchem.2004.08.020

Cited by 178 publications

(73 citation statements)

References 67 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Drawbacks of these reactions are the high temperature required (150-250°C) and the use of stoichiometric amounts of copper(I) cyanide, which leads to equimolar amounts of heavy metal waste. On an industrial scale, aryl cyanides are mainly produced via ammoxidation of the corresponding toluene derivatives [6]. Since the discovery of transition metal catalyzed cross-coupling reactions, a great deal of interest has been dedicated to the development of a practical catalytic version of this transformation [7].…”

Section: Introductionmentioning

confidence: 99%

“…In 2004, Beller et al introduced potassium ferrocyanide, K 4 [Fe(CN) 6 ], as a novel cyanation reagent with lower toxicity and without special precautions for handling [21]. This reagent is used industrially for metal extractions for the fabrication of a range of advanced materials.…”

Section: Introductionmentioning

confidence: 99%

“…This reagent is used industrially for metal extractions for the fabrication of a range of advanced materials. It is also used in low doses in some food preparations [11] and as an anti-agglutinating auxiliary for NaCl [6].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Microwave-enhanced cyanation of aryl halides with a dimeric ortho-palladated complex catalyst

Hajipour

Abrisham

Tavakoli

2011

Transition Met Chem

View full text Add to dashboard Cite

A new dimeric ortho-palladated complex of 2-methoxyphenethylamine was synthesized and characterized and its application as a cyanation catalyst was investigated. The main advantages of this catalyst are its easy preparation, handling, stability, and moisture insensitivity. Thus, [Pd{C 6 H 3 (CH 2 CH 2 NH 2 )-4-OMe-5-j 2 -C,N}(l-Br)] 2 showed excellent catalytic activity for the cyanation of aryl iodides and bromides with K 4 [Fe(CN) 6 ], in DMF in the presence of K 2 CO 3 under microwave irradiation and conventional heating at 130°C to give the desired cyanoarene products in good to high yields. The less reactive aryl chlorides also react with K 4 [Fe(CN) 6 ] to give moderate yields of the aromatic nitriles. The effects of various parameters such as solvent, base, and amount of catalyst were studied. The reaction is suitable for a wide variety of substituted aryl halides with different electronic properties. Application of microwave irradiation improved the yields of the reactions and reduced the reaction times from hours to minutes.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Microwave-enhanced cyanation of aryl halides with a dimeric ortho-palladated complex catalyst

Hajipour

Abrisham

Tavakoli

2011

Transition Met Chem

View full text Add to dashboard Cite

show abstract

“…The majority require the use of toxic inorganic or organic cyanide sources, such as alkali-metal cyanides, trimethylsilyl cyanide [49], or acetone cyanohydrin (for a review see [50], [51]). In 2004, Beller and co-workers reported the use of potassium hexacyanoferrate(II), K 4 [Fe(CN) 6 ], as a cyanide source [52,53]. This has greatly reduced toxicity as compared to alkali metal cyanides such as KCN.…”

Section: Introductionmentioning

confidence: 99%

Development of Methodologies for Copper-Catalyzed C–O Bond Formation and Direct Cyanation of Aryl Iodides

2010

View full text Add to dashboard Cite

We present a new methodology using copper(I) oxide as a catalyst in conjunction with cesium carbonate as a base for the preparation of diaryl and aryl-alkyl ethers. A range of aryl iodides, phenols and primary alcohols can be used as substrates and reactions are performed using microwave heating. We also present the use of Cu 2 Fe(CN) 6 as both catalyst and cyanating agent for the direct conversion of aryl iodides to nitriles.

show abstract

“…Cyanierungen erfordern aufgrund der besonderen Eigenschaften des Cyanidions andersartige Reaktionsbedingungen. Hier konnte u. a. ein ligandfreies Katalysatorsystem entwickelt werden [8].…”

Section: Introductionunclassified

Neues Zentrum für Angewandte Katalyseforschung: Institute aus Berlin und Rostock fusionieren zum Leibniz‐Institut für Katalyse e. V. an der Universität Rostock

Zapf

Rosenthal

2006

Chemie Ingenieur Technik

View full text Add to dashboard Cite

Improving palladium-catalyzed cyanation of aryl halides: development of a state-of-the-art methodology using potassium hexacyanoferrate(II) as cyanating agent

Cited by 178 publications

References 67 publications

Microwave-enhanced cyanation of aryl halides with a dimeric ortho-palladated complex catalyst

Microwave-enhanced cyanation of aryl halides with a dimeric ortho-palladated complex catalyst

Development of Methodologies for Copper-Catalyzed C–O Bond Formation and Direct Cyanation of Aryl Iodides

Neues Zentrum für Angewandte Katalyseforschung: Institute aus Berlin und Rostock fusionieren zum Leibniz‐Institut für Katalyse e. V. an der Universität Rostock

Contact Info

Product

Resources

About