Reactions of (polyhaloaryl)copper compounds with aryl, alkyl and allyl halides

Jukes, A. E.; Dua, S. S.; Gilman, Henry

doi:10.1016/s0022-328x(00)84513-1

Cited by 29 publications

(6 citation statements)

References 20 publications

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“…The first studies on pentafluorophenyl copper date back to reports by Cairncross and Sheppard, 2,7 DePasquale and Tamborski, 3 and Gilman et al 8 on its synthesis from the Grignard reagent C 6 F 5 MgX or the organolithium species C 6 F 5 Li through reaction with copper halides CuX (X = Cl, Br, I). Given the thermal lability of C 6 F 5 Li and the tendency to form cuprates with copper halides, the Grignard procedure is generally preferable (Scheme 1).…”

Section: Synthesis and Characterization Of Cuc 6 F 5 Preparationmentioning

confidence: 99%

Pentafluorophenyl copper: aggregation and complexation phenomena, photoluminescence properties, and applications as reagent in organometallic synthesis

Jäkle

2007

Dalton Trans.

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Recent advances in the chemistry of pentafluorophenyl copper are discussed, including the observation of strongly luminescent adducts with pyridine, the first successful structural characterization of an organocopper-arene complex, and the complexation with electron-rich transition metal complexes such as ferrocene derivatives. In addition, new applications in synthetic organometallic chemistry are discussed, which include the discovery of tin/copper exchange reactions for the preparation of organocopper compounds that are otherwise not readily accessible, and the selective transfer of the C(6)F(5) groups to boron to form catalytically active and electronically interesting organoboron polymers.

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Section: Synthesis and Characterization Of Cuc 6 F 5 Preparationmentioning

confidence: 99%

Pentafluorophenyl copper: aggregation and complexation phenomena, photoluminescence properties, and applications as reagent in organometallic synthesis

Jäkle

2007

Dalton Trans.

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“…2,3,4,5,6‐Pentafluoro‐2′‐methoxy‐1,1′‐biphenyl (8 c) :[ 17f , 21 ] Compound 8 c was synthesized from 7 (168 mg, 1.0 mmol) and 1‐iodo‐2‐methoxybenzene (234 mg, 1.0 mmol) in accordance with the general procedure. Purification by column chromatography ( n ‐hexane) afforded 149 mg of compound 8 c as a white solid (54 % yield).…”

Section: Methodsmentioning

confidence: 99%

“…Analytical data are in agreement with those previously reported in the literature. [ 17f , 21 ] R f ( n ‐hexane)=0.35; 1 H NMR (500 MHz, CDCl 3 ): δ =7.47 (ddd, J =8.3, 7.5, 1.7 Hz, 1H), 7.23 (d br, J =7.5 Hz, 1H), 7.06 (td, J =7.5, 1.0 Hz, 1H), 7.03 (d, J =8.3 Hz, 1H), 3.81 ppm (s, 3H); 13 C NMR (126 MHz, CDCl 3 ): δ =157.3, 144.6 (m, incl. app.…”

Section: Methodsmentioning

confidence: 99%

Infrared Irradiation‐Assisted Solvent‐Free Pd‐Catalyzed (Hetero)aryl‐aryl Coupling via C−H Bond Activation

et al. 2021

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The increasing attention towards environmentally friendly synthetic protocols has boosted studies directed to the development of green and sustainable methods for direct C−H bond arylation of (hetero)arenes. In this context, here the infrared (IR) irradiation‐assisted solvent‐free Pd‐catalyzed direct C−H bond arylation of (hetero)arenes was achieved. Several heteroaryl‐aryl coupling reactions were described, also involving heterocycles commonly used as building blocks for the synthesis of organic semiconductors. The reaction tolerated many functional groups on the aromatic nuclei. The IR‐irradiation as the energy source compared favorably with thermal heating and, in combination with solvent‐free conditions, provided an important contribution to the development of protocols fitting with the principles of green chemistry.

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“…Pentachlorophenyllithium (XVIII) has been prepared by Rausch and co-workers [208], and other authors [58,203,[209][210][211][212][213][214][215][216] , also by metal-halogen exchange with n-butyllithium at low temperatures (--70°C), generally in THFl…”

Section: (F) Reductionsmentioning

confidence: 99%