Copper-catalyzed coupling reaction of aryl and vinyl halides with terminal alkynes

Okuro, Kazumi; Furuune, Makoto; Miura, Masahiro; Nomura, Masakatsu

doi:10.1016/s0040-4039(00)79093-9

Cited by 80 publications

(21 citation statements)

References 10 publications

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“…According to GC‐MS data (entry 6), in 7 hours, in the reaction mixture, iodide 1a (14%), alkyne‐1 2d (5%), tolane 3e (62%), and buta‐1,3‐diyne 4a (18%) are detected. Noteworthy, earlier in various palladium‐free Cu(I)‐catalyzed Sonogashira cross‐couplings, the formation of buta‐1,3‐diyne was not observed . For the comparison purpose, we have implemented a similar reaction with the Ph 3 P (system A ) .…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, over two last decades, the researchers have focused their attention on the development of palladium‐free version of the Sonogashira cross‐coupling. The first successful results in this area were disclosed by Miura et al who showed that triphenylphosphine (Ph 3 P) turned out to be the most efficient ligand in the Sonogashira reaction, while other phosphorus‐containing ligands, (PhO) 3 P, n ‐BuPPh 2 , and ( n ‐Bu) 3 P, exerted a significantly lower activity. At the moment, the search for new catalytic systems deprived from costly palladium catalysts with using different ligands keeps being continued …”

Section: Introductionmentioning

confidence: 99%

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Tri(1‐naphthyl)phosphine as a ligand in palladium‐free Sonogashira cross‐coupling of arylhalogenides with acetylenes

Govdi

Vasilevsky

Малышева

et al. 2018

Heteroatom Chemistry

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Tri(1‐naphthyl)phosphine (Np3P) has been easily prepared in 34% yield from red phosphorus and 1‐bromonaphthalene in the superbasic system t‐BuONa/DMSO. The expedient procedures for the synthesis of aryl acetylenes by Sonogashira coupling of aryl iodides with terminal alkynes using Np3P as a ligand have been developed. For the first time, it is found that the reaction with compounds containing electron‐donating substituents preferably affords buta‐1,3‐diynes.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Tri(1‐naphthyl)phosphine as a ligand in palladium‐free Sonogashira cross‐coupling of arylhalogenides with acetylenes

Govdi

Vasilevsky

Малышева

et al. 2018

Heteroatom Chemistry

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“…Despite of the early success of PPh 3 ,– a range of commercial available ligands including EN, DMEDA,– DABCO, pyrimidines, acac, [6i] rac ‐BINOL, [6j] salicylic acid and methionine– were found to accelerate the copper‐catalyzed Sonogashira reaction. A key advantage of these simple ligands for copper over some others was the easily access to bidentated coordination mode, and consequently stabilized catalytic active species.…”

Section: Methodsmentioning

confidence: 99%

Triazine‐Triazole Conjugates as Potent Ligands for Cu–Catalyzed Sonogashira Reaction

Wang

Sun

et al. 2016

ChemistrySelect

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Triazine Triazole conjugates (TT) were developed as efficient ligand system for CuSO 4 ·5H 2 O catalyzed Sonogashira and decarboxylative cross-coupling reaction. This new protocol showed good compatibility with a broad range of substitutents and afforded moderate to excellent yields. TT ligands are rapid constructed and highly modular electronically and sterically.Alkyne products obtained via Sonogashira reaction widely used in the most diverse areas of chemistry, such as dyes, sensors, electronics, polymers, guest-host constructs, natural products and heterocycle synthesis. [1][2] The classic Sonogashira coupling procedures relied on palladium as catalyst, and originally copper iodide was added to facilitate the transmetallation of alkynyl moiety. [3] The high cost of palladium salts, requirement of copper co-catalyst, high oxophillicity associated with phosphine ligands have rendered Pd unpopular, particularly for large-scale reactions. For these reasons, much recent effort has been made to achieve the Sonogashira reaction in absence of the expensive noble metal palladium and using more sustainable metals like Fe, [4] Ni [5] and Cu. [6] Among them, copper is a potent alternative to the palladium in a large variety of CÀN, CÀO, and CÀC cross-coupling reactions. These Cu-catalyzed reactions are robust, can be performed with simple ligands, making them highly attractive to these engaged in the synthesis of complex molecular architecture. [7] Despite of the early success of PPh 3 , [6a-c] a range of commercial available ligands including EN, [6d] DMEDA, [6e-f] DABCO, [6g] pyrimidines, [6h] acac, [6i] rac-BINOL, [6j] salicylic acid [6k] and methionine [6l-m] were found to accelerate the copper-catalyzed Sonogashira reaction. A key advantage of these simple ligands for copper over some others was the easily access to bidentated coordination mode, and consequently stabilized catalytic active species. The steric and electronic optimization on these simple molecules also enhanced the activity of copper catalyst. N,N'dibenzyl-BINAM, [6n] diphenylpropane-1,3-dione, [6o] N,N'-di-8-quinolylamidinates, [6p] N,N-dimethylglycine [6q] were prepared ac- [a]

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“…Ausbeute [%] [a] t [154,155] Vorgeschlagen wurde ein Reaktonsmechanismus, bei dem anfänglich eine Kupferacetylid-Spezies gebildet wird, die das für die Reaktion unverzichtbare PPh 3 koordiniert. [155] Neuerdings wurden einige weitere Kupfer-Katalysatorsysteme vorgestellt (Schema 61), in denen ein Stickstoffdonorligand das Triphenylphosphan ersetzt; [156,157] aufgrund der erforderlichen Metallmenge (10 Mol-%) und Temperatur sind diese Systeme nicht besser als der Katalysator von Miura für die Alkinylierung von Aryliodiden.…”

Section: Arylsubstratunclassified

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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Copper-catalyzed coupling reaction of aryl and vinyl halides with terminal alkynes

Cited by 80 publications

References 10 publications

Tri(1‐naphthyl)phosphine as a ligand in palladium‐free Sonogashira cross‐coupling of arylhalogenides with acetylenes

Tri(1‐naphthyl)phosphine as a ligand in palladium‐free Sonogashira cross‐coupling of arylhalogenides with acetylenes

Triazine‐Triazole Conjugates as Potent Ligands for Cu–Catalyzed Sonogashira Reaction

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

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