Synthesis of poly(3-phenyl-2,5-thiophene) by nickel-catalyzed coupling polymerization of 3-phenyl-2,5-dichlorothiophene

Ueda, Mitsuru; Miyaji, Yoshiyuki; Ito, Takashi; Oba, Yoshihiro; Sone, Tyo

doi:10.1021/ma00010a008

Cited by 61 publications

(37 citation statements)

References 5 publications

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“…[6][7][8][9][10] Nickel reactions facilitated by the addition of zinc powder have been utilized in a similar fashion in organic synthesis, [11][12][13] as well as in efficient condensation polymerizations. [14][15][16] These reactions are not always well controlled, require prolonged heating at high temperatures, and the products have high levels of metal impurities that can be difficult and costly to remove. This trace-metal contamination is especially problematic if the end use is in pharmaceutical or microelectronic applications in which safety, performance, and reliability require stringent control of purity.…”

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confidence: 99%

Nickel‐Catalyzed Coupling of Aryl Bromides in the Presence of Alkyllithium Reagents

Jhaveri¹,

Carter²

2008

Chemistry A European J

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Transition-metal-catalyzed coupling reactions of halogenated molecules leading to formation of new carbon-carbon bonds are a very important category of reactions used in the synthesis of complex compounds and conjugated polymers. [1][2][3] Within the past decade, this methodology has evolved into a powerful synthetic tool for the preparation of a wide range of specialty polymers, composite materials, and pharmaceutically active compounds both in the laboratory and on the industrial scale. It is also widely appreciated in the context of parallel synthesis and combinational chemistry. [4,5] We desired to develop an improved catalytic method for transition-metal-catalyzed aryl coupling reactions and report herein the one-pot, one-step, nickel-catalyzed coupling of aryl bromides in the presence of alkyllithium reagents [Eq. (1)].Metallic reagents including palladium and nickel complexes have demonstrated to be quite effective in C À C coupling reactions. Typically, coupling reactions of aryl halides involving the use of catalytic amounts of nickel(II) complexes require the addition of either magnesium or zinc to facilitate efficient coupling and regeneration of active nickel(0) catalytic species. For example, Kumada coupling reactions use magnesium for the formation of active alkyl/ aryl magnesium bromide species (Grignard formation), which is generally a substrate-and solvent-specific reaction (working optimally in tetrahydrofuran or diethyl ether as solvents). [6][7][8][9][10] Nickel reactions facilitated by the addition of zinc powder have been utilized in a similar fashion in organic synthesis, [11][12][13] as well as in efficient condensation polymerizations. [14][15][16] These reactions are not always well controlled, require prolonged heating at high temperatures, and the products have high levels of metal impurities that can be difficult and costly to remove. This trace-metal contamination is especially problematic if the end use is in pharmaceutical or microelectronic applications in which safety, performance, and reliability require stringent control of purity. Another known aryl-halide coupling reaction involves the use of highly reactive zinc (Rieke zinc), which is prepared by reduction of ZnCl 2 with lithium naphthalenide and has been shown to readily undergo oxidative addition with alkyl, aryl, and vinyl halides under mild conditions to generate the corresponding organozinc compounds. These reactive organozinc compounds are then cross-coupled with other aryl or vinyl halides using palladium(0) catalysts. [17] Recently, homocoupling of bromide compounds has been facilitated through the combination of metallic magnesium and a catalytic amount of iron salts.[18] Coupling reactions involving activated dihalogenated thiophene molecules catalyzed by nickel(II) complexes have also been demonstrated in the presence of reactive zinc (Rieke zinc) [19] or an alkylmagnesium reagent (GRIM/McCullough method) [20] to form regioregular polythiophenes.Coupling reactions of halogenated molecules involving nickel(0) compl...

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Nickel‐Catalyzed Coupling of Aryl Bromides in the Presence of Alkyllithium Reagents

Jhaveri¹,

Carter²

2008

Chemistry A European J

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“…n X‐arylene‐X + n [Ni(0)L m ] → –(arylene) n –; arylene = p ‐phenylene, etc.) . π‐Conjugated polymers have been the focus of numerous studies because of their attractive chemical and physical properties…”

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confidence: 99%

Homocoupling of aryl halides promoted by an NiCl₂/bpy/Mg system in DMF

Yamamoto

2014

Applied Organom Chemis

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Homocoupling of aryl halides (2 ArX → Ar-Ar) promoted by NiCl 2 /2,2′-bipyridine (bpy)/Mg mixtures in DMF has been studied. Mixtures of NiCl 2 , bpy and Mg in DMF promoted homocoupling of aryl halides such as phenyl bromide and p-tolyl bromide to give the coupling products in good (e.g. approximately 60-75%) yields, and the homocoupling products were easily isolated from the reaction mixtures. Application of this homocoupling to dibromo-aromatic compounds (Br-arylene-Br: 2,5-dibromopyridine, 2,7-dibromo-9.9-dioctylfluorene and 2,7-dibromo-9,10-dioctyl-9,10-dihydrophenanthrene) gave the corresponding π-conjugated polymers, -(arylene) n -, in good yields. Organometallic processes for the homocoupling are discussed.

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“…There are several known synthetic routes to prepare poly-(arylene ether) (PAE) such as Ullman reactions, [14,15] nickelcoupling reactions, [16,17] and reactions between masked diphenol and trimethylsilyl or silyl groups. [18] These routes are, however, usually challenging owing to several problems such as incomplete removal of catalysts, difficulties in obtaining high molecular weights, and/or limited monomer structures.…”

Section: Introductionmentioning

confidence: 99%

“…The most widely used method for synthesizing PAE is nucleophilic aromatic substitution (SNAr) which also has some restrictions. [1,2,17,18] For example, this reaction requires high temperatures (120-180 8C) resulting in side reactions such as intermolecular cross-linking reactions. In this study, we report a new synthetic method towards fluorinated poly(arylene ethers) (F-PAE) from decafluorinated chalcone and fluorinated bisphenol at low temperature.…”

Section: Introductionmentioning

confidence: 99%

Novel Photosensitive Fluorinated Poly(arylene ether) Having Zero Birefringence

Zhong

Kim

et al. 2004

Macromol. Rapid Commun.

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Summary: A novel photosensitive fluorinated poly(arylene ether) containing chalcone units was synthesized from decafluorinated chalcone and fluorinated bisphenol at low temperature. Upon UV irradiation, the refractive indices of the polymer film were decreased because of the reduction of electronic polarizability in the chalocone moiety. The decrease was more significant in the in‐plane direction than in the out‐of‐plane direction, and consequently, zero birefringence (at 632.8 nm) was obtained after 90 s of exposure.The changes in the refractive indices and the birefringence of chalcone‐containing fluorinated poly(arylene ether) films synthesized and measured at 632.8 nm with respect to UV irradiation time.imageThe changes in the refractive indices and the birefringence of chalcone‐containing fluorinated poly(arylene ether) films synthesized and measured at 632.8 nm with respect to UV irradiation time.

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Synthesis of poly(3-phenyl-2,5-thiophene) by nickel-catalyzed coupling polymerization of 3-phenyl-2,5-dichlorothiophene

Cited by 61 publications

References 5 publications

Nickel‐Catalyzed Coupling of Aryl Bromides in the Presence of Alkyllithium Reagents

Nickel‐Catalyzed Coupling of Aryl Bromides in the Presence of Alkyllithium Reagents

Homocoupling of aryl halides promoted by an NiCl₂/bpy/Mg system in DMF

Novel Photosensitive Fluorinated Poly(arylene ether) Having Zero Birefringence

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Synthesis of poly(3-phenyl-2,5-thiophene) by nickel-catalyzed coupling polymerization of 3-phenyl-2,5-dichlorothiophene

Cited by 61 publications

References 5 publications

Nickel‐Catalyzed Coupling of Aryl Bromides in the Presence of Alkyllithium Reagents

Nickel‐Catalyzed Coupling of Aryl Bromides in the Presence of Alkyllithium Reagents

Homocoupling of aryl halides promoted by an NiCl2/bpy/Mg system in DMF

Novel Photosensitive Fluorinated Poly(arylene ether) Having Zero Birefringence

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Homocoupling of aryl halides promoted by an NiCl₂/bpy/Mg system in DMF