Electrosynthesis of heteroaromatic aldehydes by palladium-catalyzed carbonylation of heteroaromatic iodides in the presence of formic acid

Chiarotto, Isabella; Feroci, Marta

doi:10.1016/j.jorganchem.2006.01.054

Cited by 7 publications

(7 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…A totally different electrochemical approach to aromatic and heteroaromatic aldehydes was presented by Chiarotto et al [81] Based on preliminary investigations, [82] the formylation of aryl iodides was accomplished in the presence of formic acid and an atmospheric pressure of carbon monoxide. [81b] The necessary formate ions for an efficient formylation were generated from HCOOH in the presence of 10 mol % palladium-phosphane complexes under electrolytic conditions (À1.2 V versus SCE).…”

Section: Reductive Carbonylationmentioning

confidence: 99%

Palladium‐Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds

2009

View full text Add to dashboard Cite

Palladium-catalyzed carbonylation reactions of aromatic halides in the presence of various nucleophiles have undergone rapid development since the pioneering work of Heck and co-workers in 1974, such that nowadays a plethora of palladium catalysts are available for different carbonylative transformations. The carboxylic acid derivatives, aldehydes, and ketones prepared in this way are important intermediates in the manufacture of dyes, pharmaceuticals, agrochemicals, and other industrial products. In this Review, the recent academic developments in this area and the first industrial processes are summarized.

show abstract

Section: Reductive Carbonylationmentioning

confidence: 99%

Palladium‐Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds

2009

View full text Add to dashboard Cite

show abstract

“…The development of electrochemical functionalization reaction of aryl iodide and aryl bromide which emerged earlier is relatively mature. [78][79][80][81][82] Undoubtedly, it had been proved that Pd might effectively facilitate the formylation reaction of aryl iodide/heteroaryl iodide with CO at atmospheric pressure in the presence of formic acid to produce the corresponding aldehyde. [79,80] Chiarotto et al reported that Pd coordinated by tertiary amines was used for the coupling of heteroaromatic iodides and CO to generate heteroaromatic aldehydes.…”

Section: Halogenated Hydrocarbon-based Electrocatalytic Carbonylationmentioning

confidence: 99%

“…[78][79][80][81][82] Undoubtedly, it had been proved that Pd might effectively facilitate the formylation reaction of aryl iodide/heteroaryl iodide with CO at atmospheric pressure in the presence of formic acid to produce the corresponding aldehyde. [79,80] Chiarotto et al reported that Pd coordinated by tertiary amines was used for the coupling of heteroaromatic iodides and CO to generate heteroaromatic aldehydes. It was precisely the use of formic acid as a proton source that avoided the use of high-pressure hydrogen (Scheme 18 Chiarotto).…”

Section: Halogenated Hydrocarbon-based Electrocatalytic Carbonylationmentioning

confidence: 99%

“…It was precisely the use of formic acid as a proton source that avoided the use of high-pressure hydrogen (Scheme 18 Chiarotto). [80] The ionic liquid was employed in the silver-catalyzed aminobromopyridine carboxylation reaction in a non-separating electrolytic cell, with a yield of 75% and no other products were detected (Scheme 18 Huang). [81] Cyclic voltammetry was used to compare the catalytic ability of various transition metals on bromobenzene: Ag, Cu, and Au all showed better activity than glassy carbon electrodes.…”

Section: Halogenated Hydrocarbon-based Electrocatalytic Carbonylationmentioning

confidence: 99%

See 1 more Smart Citation

Electrochemical Approaches to Carbonylative Coupling Reactions

Shi

Xia

Huang

2021

Chemistry An Asian Journal

View full text Add to dashboard Cite

The carbonylation reaction is an effective way to introduce CO or other carbonyl groups into organic compounds, and widely used in the preparation of aldehydes, ketones, amides, and esters. The replacement of conventional reaction approaches by greener electrochemical methods is appealing with great synthetic potential as well as inherent safety, owing to the avoidance of external oxidants or reductants and a more facile control in product selectivity. In this minireview, we give a summary of the recent development of carbonylation reactions via the electrochemical approach.

show abstract

“…Diese Methode ergab für die meisten Produkte gute Ausbeuten. Die analoge elektrochemische Carbonylierung von Iodthiophenen, ‐furanen und ‐pyridinen mit dem phosphanfreien Katalysatorsystem Pd(OAc) 2 /DABCO lieferte mäßige bis gute Ausbeuten 81a…”

Section: Reduktive Carbonylierungenunclassified

Palladiumkatalysierte Carbonylierungen von Arylhalogeniden und ähnlichen Substraten

2009

View full text Add to dashboard Cite

Um eine CO‐Gruppe reicher: (Hetero‐)Arene sind aus der industriellen Herstellung von Agrochemikalien, Farbstoffen, Pharmaka etc. nicht wegzudenken. Während der vergangenen Jahrzehnte wurden übergangsmetallkatalysierte Kupplungen von Arylhalogeniden mit Nucleophilen aller Art entwickelt. Dieser Aufsatz fasst aktuelle Fortschritte auf dem Gebiet der palladiumkatalysierten Carbonylierungen von Arylhalogeniden und ähnlichen Verbindungen zusammen (siehe Schema). Palladiumkatalysierte Carbonylierungen von Arylhalogeniden in Gegenwart verschiedener Nucleophile haben sich seit ihrer Einführung durch Heck und Mitarbeiter im Jahr 1974 schnell weiterentwickelt, sodass heute eine Vielzahl von Palladiumkatalysatoren für unterschiedliche Carbonylierungsreaktionen verfügbar ist. Auf diesem Weg erhältliche Carbonsäurederivate, Aldehyde und Ketone sind wichtige Zwischenstufen bei der industriellen Herstellung von Farbstoffen, Pharmaka, Agrochemikalien und anderen Produkten. In diesem Aufsatz werden aktuelle Ergebnisse aus der akademischen Forschung und erste industrielle Prozesse zusammengefasst.

show abstract

Electrosynthesis of heteroaromatic aldehydes by palladium-catalyzed carbonylation of heteroaromatic iodides in the presence of formic acid

Cited by 7 publications

References 19 publications

Palladium‐Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds

Palladium‐Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds

Electrochemical Approaches to Carbonylative Coupling Reactions

Palladiumkatalysierte Carbonylierungen von Arylhalogeniden und ähnlichen Substraten

Contact Info

Product

Resources

About