Rapid Homogeneous-Phase Sonogashira Coupling Reactions Using Controlled Microwave Heating

Erdélyi, Máté; Gogoll, Adolf

doi:10.1021/jo0057250

Cited by 188 publications

(126 citation statements)

References 38 publications

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“…[83] General protocols for microwave-assisted Sonogashira reactions under controlled conditions were first reported in 2001 by ErdØlyi and Gogoll. [84] Typical reaction conditions for the coupling of aryl iodides, bromides, chlorides, and triflates involve DMF as the solvent, diethylamine as the base, and [PdCl 2 (PPh 3 ) 2 ] (2-5 mol %) as the catalyst with CuI (5 mol %) as an additive. [84] Gogoll and co-workers later utilized these protocols in a rapid domino Sonogashira sequence to synthesize amino ester 6 (Scheme 7).…”

Section: Sonogashira Reactionsmentioning

confidence: 99%

“…[84] Typical reaction conditions for the coupling of aryl iodides, bromides, chlorides, and triflates involve DMF as the solvent, diethylamine as the base, and [PdCl 2 (PPh 3 ) 2 ] (2-5 mol %) as the catalyst with CuI (5 mol %) as an additive. [84] Gogoll and co-workers later utilized these protocols in a rapid domino Sonogashira sequence to synthesize amino ester 6 (Scheme 7). [85] Essentially the same experimental protocol was employed by Vollhardt and co-workers to synthesize o-dipropynylated arene 8, which served as the precursor to tribenzocyclyne 9 through an alkyne metathesis reaction (Scheme 8).…”

Section: Sonogashira Reactionsmentioning

confidence: 99%

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Controlled Microwave Heating in Modern Organic Synthesis

2004

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Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of “microwave flash heating” in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

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Section: Sonogashira Reactionsmentioning

confidence: 99%

Section: Sonogashira Reactionsmentioning

confidence: 99%

Controlled Microwave Heating in Modern Organic Synthesis

2004

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“…Then the ethyl 7-anilinopyrrolo[1,2-a]quinoxaline-4-carboxylates 12k,l were synthesized via the Buchwald palladiumcatalyzed cross-coupling reaction of 3-chloroaniline or 3-(trimethylsilylethynyl)aniline [37,38] with 16 in the presence of BINAP and cesium carbonate (Scheme 3). The deprotection of the acetylene moiety of compound 12l by tetrabutylammonium fluoride (TBAF) led to anilinopyrrolo[1,2-a]quinoxaline 17 [39,40].…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and biological evaluation of novel substituted pyrrolo[1,2-a]quinoxaline derivatives as inhibitors of the human protein kinase CK2

Guillon¹,

Borgne²,

Rimbault³

et al. 2013

European Journal of Medicinal Chemistry

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a b s t r a c tHerein we describe the synthesis and properties of substituted phenylaminopyrrolo[1,2-a]quinoxalinecarboxylic acid derivatives as a novel class of potent inhibitors of the human protein kinase CK2. A set of 15 compounds was designed and synthesized using convenient and straightforward synthesis protocols. The compounds were tested for inhibition of human protein kinase CK2, which is a potential drug target for many diseases including inflammatory disorders and cancer. New inhibitors with IC 50 in the microand sub-micromolar range were identified. The most promising compound, the 4-[(3-chlorophenyl) amino]pyrrolo[1,2-a]quinoxaline-3-carboxylic acid 1c inhibited human CK2 with an IC 50 of 49 nM. Our findings indicate that pyrrolo[1,2-a]quinoxalines are a promising starting scaffold for further development and optimization of human protein kinase CK2 inhibitors.

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“…[148] Ohne Lösungsmittelzusatz und bei gründlicher Durchmischung konnte eine Vielzahl von Ein Vergleich der veröffentlichten Daten zeigt, dass die Reaktionen unter Mikrowellenbestrahlung etwa 20-bis 100-mal schneller ablaufen. [149] Die Kupplung von desaktivierten Halogeniden wie Bromanisol, ortho-substituierten Substraten und einem Heteroarylchlorid in hoher Ausbeute ist eine bemerkenswerte Leistung. Die Trimethylsilylgruppe ermöglicht eine weitere Funktionalisierung der Enine, es ist aber sicherlich auch von Interesse, dieses Systems mit anderen terminalen Alkinen zu erproben.…”

Section: Katalyse Mit Mikrowellenstrahlungunclassified

Palladium‐Katalysatorsysteme für die Synthese von konjugierten Eninen durch Sonogashira‐Kupplungen und verwandte Alkinylierungen

2007

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Konjugierte Alkine sind stets wiederkehrende Synthesebausteine in Naturstoffen, zahlreichen unverzichtbaren industriellen Zwischenstufen, in Pharmazeutika und Agrochemikalien sowie in molekularen Materialien für Optik und Elektronik. Daher zählt die palladiumkatalysierte Verknüpfung der sp2‐hybridisierten Kohlenstoffatome von Aryl‐, Heteroaryl‐ und Vinylhalogeniden mit den sp‐hybridisierten Kohlenstoffatomen von terminalen Acetylenen in einer Kreuzkupplung unbestreitbar zu den bedeutendsten Entwicklungen der Alkinchemie in den vergangenen fünfzig Jahren. Auf die grundlegenden Arbeiten der 1970er folgte eine intensive Suche nach allgemeineren und verlässlicheren Reaktionsbedingungen. Das Interesse an einer katalytischen Aktivierung anspruchsvoller Substrate, die unbedingte Notwendigkeit, den Ressourcenverbrauch zu minimieren, und die einfache Synthese einer stetig wachsenden Zahl an funktionalisierten Eninen führte allmählich zu den aktuellen Katalysatoren mit hohen Umsatzzahlen. Der vorliegende Aufsatz gibt einen Überblick über hoch wirksame Palladium‐Katalysatorsysteme für die direkte Alkinylierung von C(sp2)‐Halogeniden mit terminalen Alkinen in homogener oder heterogener Phase.

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Rapid Homogeneous-Phase Sonogashira Coupling Reactions Using Controlled Microwave Heating

Cited by 188 publications

References 38 publications

Controlled Microwave Heating in Modern Organic Synthesis

Controlled Microwave Heating in Modern Organic Synthesis

Synthesis and biological evaluation of novel substituted pyrrolo[1,2-a]quinoxaline derivatives as inhibitors of the human protein kinase CK2

Palladium‐Katalysatorsysteme für die Synthese von konjugierten Eninen durch Sonogashira‐Kupplungen und verwandte Alkinylierungen

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