Palladium-Catalyzed C−H Homocoupling of Thiophenes:  Facile Construction of Bithiophene Structure

Masui, Kentaro; Ikegami, Haruka; Mori, Atsunori

doi:10.1021/ja031855p

Cited by 302 publications

(102 citation statements)

References 21 publications

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“…B. als organische Dünn-filmtransistoren, Flüssigkristalle oder Solarzellen in der Elektronik und Photonik von Bedeutung sind. [58] 2-Arylpyridine konnten in der chelatkontrollierten palladiumkatalysierten dehydrierenden Homokupplung mit Pd-(OAc) 2 als Katalysator und Oxon als stöchiometrischem Oxidationsmittel umgesetzt werden (Schema 30). [59] Interessanterweise verliefen diese Umsetzungen selbst bei Umgebungstemperatur mit hoher Effizienz.…”

Section: Eisenkatalysierte Direkte Arylierungen Mit Metallorganischenunclassified

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

2009

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Das Gebiet der übergangsmetallkatalysierten direkten Arylierung unter C‐H‐Bindungsbruch hat in den letzten Jahren eine rasante Entwicklung erfahren, was dazu führte, dass sich solche Methoden immer mehr als Alternativen zu den herkömmlichen Kreuzkupplungen mit metallorganischen Reagentien etabliert haben. Insbesondere wurden zahlreiche Palladium‐ und Rutheniumkatalysatoren beschrieben, welche die direkte Arylierung von (Hetero)arenen mit anspruchsvollen Reaktionspartnern ermöglichen; hierzu gehören elektrophile Arylchloride und ‐tosylate oder auch einfache Arene in gekreuzten dehydrierenden Arylierungen.

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Section: Eisenkatalysierte Direkte Arylierungen Mit Metallorganischenunclassified

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

2009

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“…Hence, Ag + ions can be considered as terminal oxidants in these reactions. [15] The role of the Cu 2+ ions is less clear at present. We assume that, in analogy to the Wacker process, [16] Cu 2+ ions catalyze the oxidation of Pd 0 by O 2 when substoichiometric amounts of Ag + ions are applied (Table 1, entries 6 and 7).…”

Section: +mentioning

confidence: 98%

Palladium‐Catalyzed Dehydrogenative Cross‐Couplings of Benzazoles with Azoles

Han¹,

Mayer²,

Ofial³

2011

Angew Chem Int Ed

188

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“…We found that homocoupling of thiophenes took place at the CH bond adjacent to the sulfur atom by treatment of a catalytic amount of palladium and silver(I) fluoride. 24 Several thiophene derivatives bearing a substituent such as formyl, ethoxycarbonyl, acetyl, methyl, and aryl groups underwent the reaction. Benzothiophene and a thiazole derivative (5-position) also homocoupled smoothly as summarized in Table 14.…”

Section: Reactions At the Ch Bond Of Thiophene Derivativesmentioning

confidence: 99%

Palladium-Catalyzed CH Arylation and Dehydrogenative Homocoupling of Heteroaromatic Compounds and Application to the Design of Advanced Organic Materials

Mori¹,

Sugie²

2008

Bulletin of the Chemical Society of Japan

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125

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CH arylation of five-membered heteroaromatic compounds such as thiazoles and thiophenes recently developed by the authors is reviewed. The reaction of thiazole with aryl iodides in the presence of a palladium/copper catalyst system and tetrabutylammonium fluoride causes CH arylation at the 2-position of thiazole. The reaction of 2-arylthiazole with aryl iodide by the catalysis of a palladium complex with silver(I) fluoride induces CH arylation at the 5-position. The reactions allow preparation of a variety of 2,5-diarylthiazoles in a facile manner. Spectroscopic, thermal, and electrochemical characteristics of 2,5-diarylthiazole are summarized. Introduction of the 2,5-diarylthiazole moiety, which exhibits photoluminescent and liquid crystalline characteristics, into the side chain of polymethacrylate is also described. CH arylation of thiophene derivatives are described to occur similarly to the case of thiazole. CH homocoupling of thiophene leading to bithiophene, in which the carbon-bromine bond on the thiophene ring is completely intact in the palladium-catalyzed reaction, is also described. Mechanistic studies on the reactions of thiophene are shown with a stoichiometric use of arylpalladium(II) halide complex and thiophene to undergo electrophilic substitution at the thiphene ring toward the palladium atom and the following reductive elimination of the thus obtained aryl(thienyl)-palladium complex.

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Palladium-Catalyzed C−H Homocoupling of Thiophenes: Facile Construction of Bithiophene Structure

Cited by 302 publications

References 21 publications

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

Übergangsmetallkatalysierte direkte Arylierungen von (Hetero)Arenen durch C‐H‐Bindungsbruch

Palladium‐Catalyzed Dehydrogenative Cross‐Couplings of Benzazoles with Azoles

Palladium-Catalyzed CH Arylation and Dehydrogenative Homocoupling of Heteroaromatic Compounds and Application to the Design of Advanced Organic Materials

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