C60-catalyzed direct C–H arylation of benzene with aryl iodides in air

Kwok, Tsz Yiu; Sonnenschein, Christoph; To, Ching Tat; Liu, Jianwen; Chan, Kin Shing

doi:10.1016/j.tet.2015.04.044

Cited by 8 publications

(4 citation statements)

References 49 publications

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“…Then 3f undergoes base-promoted β-H elimination to generate M(ttp)H and regenerates thiophene. Alternatively, direct aromatization of the allylic radical 3e with O 2 also generates M(ttp)(2-thienyl) . Pathway B is metalloradical addition to thiophene to give 3g and subsequent base-promoted β-H elimination to afford M(ttp)(2-thienyl).…”

Section: Results and Discussionmentioning

confidence: 99%

Base-Promoted, Aerobic, and Regioselective Carbon–Hydrogen Bond Activation of Thiophene with Group 9 Metalloporphyrins

Yang

Zhang

et al. 2016

Organometallics

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List of Contents 1. Reaction Conditions Optimization (S2) 2. X-ray Crystallographic Data and Structure of Rh(ttp)(2-thienyl) (3b) (S3) 3. Titration Experiments (S5) 4. NMR Spectra (S11) S2 Reaction Conditions OptimizationThe general procedures described in the experimental section were followed in the optimization reactions.(1) The reaction of Co II (ttp) with thiophene:Co II (ttp) (1a; 11.3 mg, 0.0155 mmol) were added to thiophene (1000 µL, 12.5 mmol). The mixture was heated at 120 o C under air for 2 days. 1a was quantitatively recovered.Co II (ttp) (1a; 11.3 mg, 0.0155 mmol) were added to thiophene (1000 µL, 12.5 mmol). The mixture was degassed for three freeze-pump-thaw cycles, then filled with N 2 . It was then heated at 120 o C under N 2 for 4 days. Co(ttp)(2-thienyl) (3a) was obtained in trace yield with 83% recovery of 1a.Co II (ttp) (1a; 11.3 mg, 0.0155 mmol), KOH (8.7 mg, 0.155 mmol) were added to thiophene (1000 µL, 12.5 mmol). The mixture was heated at 140 o C under air for 6 days. Co(ttp)(2-thienyl) (3a) was obtained in 20% yield with 60% recovery of 1a.Co II (ttp) (1a; 11.3 mg, 0.0155 mmol), KOH (8.7 mg, 0.155 mmol) and H 2 O (28 µL, 1.55 mmol) were added to thiophene (1000 µL, 12.5 mmol). The mixture was heated at 140 o C under air for 8 days. 1a was quantitatively recovered.(2) The reaction of Rh III (ttp)Cl with thiophene:Temperature effects: Rh(ttp)Cl (1b; 11.0 mg, 0.0136 mmol), aqueous KOH (5.5 M, 24.5 µL, 0.135 mmol) were added to thiophene (1000 µL, 12.5 mmol). The mixture was heated at under air. Isolated yields of Rh(ttp)(2-thienyl) (3b) for the reaction at 180 o C for 6 h: 47%; at 200 o C for 2 h: 87%. Yields of Rh(ttp)(3-thienyl) (3c) for the reaction at 180 o C for 6 h: 4; at 200 o C for 2 h: 9%.Atmosphere effects: Rh(ttp)Cl (1b; 11.0 mg, 0.0136 mmol), aqueous KOH (5.5 M, 24.5 µL, 0.135 mmol) were added to thiophene (1000 µL, 12.5 mmol). For the reaction conducted under N 2 , the mixture was degassed for three freeze-pump-thaw cycles, then filled with N 2 .The mixture was heated at 200 o C. Rh(ttp)(2-thienyl) (3b) was obtained in 25% yield under N 2 for 4 h, and 87% yield under air. KOH loading effects: Rh(ttp)Cl (1b; 11.0 mg, 0.0136 mmol), aqueous KOH (n equiv) were added to thiophene (1000 µL, 12.5 mmol). The mixture was heated at 200 o C.

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Section: Results and Discussionmentioning

confidence: 99%

Base-Promoted, Aerobic, and Regioselective Carbon–Hydrogen Bond Activation of Thiophene with Group 9 Metalloporphyrins

Yang

Zhang

et al. 2016

Organometallics

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“…[24][25][26][27] This significant change in the corrosion behavior of the nanostructured stainless steel is mainly due to the change in the passive film structure. [28] The grain structure, the grain boundary density, and the native oxide layer differences between the microstructure and nanostructured samples are schematically demonstrated in Fig. 7.…”

Section: Resultsmentioning

confidence: 99%

“…7, the nanostructured sample possesses a higher grain boundary density, which proves the higher density of the native oxide layer on the surface of the nanostructured sample compared with the microstructure one. [17,28] The metals native oxide layer is considered as a protective layer (resistance to corrosion) against the metal reactions in the corrosive environment. [29] By increasing the thickness and density of the native oxide layer, the metal corrosion resistance will enhance significantly.…”

Section: Resultsmentioning

confidence: 99%

“…[30] Therefore, as it is expected, the corrosion resistance of the nanostructured metals is much greater than the microstructure ones. [17,28] The quick and uniform passivation on the metal surface (the native oxide on the metal surface) is considered as a rigid barrier to localized corrosion. [31] Zheng et al [32] found out that performing the eight passes of ECAP process on the 304 stainless steel resulted in a nanostructured one.…”

Section: Resultsmentioning

confidence: 99%

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Corrosion and biological behavior of nanostructured 316L stainless steel processed by severe plastic deformation

Hajizadeh

Maleki-Ghaleh

Arabi

et al. 2015

Surf. Interface Anal.

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Nanostructured metals have different mechanical, chemical, and physical behaviors in comparison with the microstructured ones. Numerous research studies demonstrated that the biological behavior of nanostructured metallic implants was improved significantly. Concerning the nanostructured metals, decreasing the corrosion rate and the releasing of hazardous ions from metallic implants, and thus increasing the biocompatibility of implants are due to improving the native oxide layer. In the present study, nanostructured 316L stainless steel (biomedical grade) was manufactured via equal channel angular pressing (ECAP) method. To do so, the 316L stainless steel (SS) was exposed to the ECAP operation for eight passes. The impact of the ECAP process on corrosion behavior of SS samples was evaluated through performing the electrochemical polarization corrosion tests in Ringer's solution. Scanning electron microscopy was employed to study the surface morphology of common SS and ECAPed SS sample after the electrochemical polarization tests. Moreover, the biological behavior of the samples was evaluated via cell culture using fibroblast cells. The corrosion test results revealed a substantial decrease of corrosion rate from 3.12 (coarse‐grained sample) to 0.42 μA cm−2 (for nanostructured). Furthermore, the cell proliferation in the interface of nanostructured sample and cell culture medium enhanced dramatically compared with the coarse‐grained one. The much better biological behavior of nanostructured SS sample in comparison with the coarse‐grained one is mostly due to the significant decrease of corrosion rate on the surface of SS samples, and the presence of much more chrome oxide on the surface of SS sample. Copyright © 2015 John Wiley & Sons, Ltd.

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fullerenes

Sloby¹

2020

Catalysis From a to Z

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C60-catalyzed direct C–H arylation of benzene with aryl iodides in air

Cited by 8 publications

References 49 publications

Base-Promoted, Aerobic, and Regioselective Carbon–Hydrogen Bond Activation of Thiophene with Group 9 Metalloporphyrins

Base-Promoted, Aerobic, and Regioselective Carbon–Hydrogen Bond Activation of Thiophene with Group 9 Metalloporphyrins

Corrosion and biological behavior of nanostructured 316L stainless steel processed by severe plastic deformation

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