Thienylbenzotriazole promoted highly active gold nanoparticles supported on N-doped graphene as efficient catalysts in water and a mechanism exploration

Ye, Dongdong; Huang, Ronghui; Zhu, Hao; Zou, Liang‐Hua; Wang, Dawei

doi:10.1039/c8qo00941d

Cited by 50 publications

(7 citation statements)

References 89 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Alcohol as one of inexpensive, stable, readily available, and less harmful substances that can be produced through the microbial fermentation of biomass plays an important role in both organic synthesis and industrial production. [ 1–4 ] Metal‐mediated utilization of alcohols as electrophiles or alkylating agents to construct C–C bonds has been considered as an atom‐economic method and has received significant attention, [ 5–7 ] because the products are known for its diverse biological and pharmaceutical properties. In the past decade, the direct cross‐coupling of secondary and primary alcohols has been developed.…”

Section: Introductionmentioning

confidence: 99%

Magnetic Fe₃O₄@Ag nanoparticles catalyzed C–C cross‐coupling reaction of aromatic alcohols

Tang

Feng

Huang

et al. 2022

Applied Organom Chemis

View full text Add to dashboard Cite

The construction of complex molecules from readily available alcohols via C–C bond formation reactions is of great interest in organic synthesis. Silver‐coated Fe3O4 nanoparticles (Fe3O4@Ag) were prepared and used as magnetic catalyst for the chemoselective C–C cross‐coupling of benzyl alcohol and 1‐phenylethanol to form 1,3‐diphenylpropan‐1‐one or 1,3‐diphenylpropan‐1‐ol. This magnetically separable catalyst was also found to exhibit high catalytic activity in one‐pot, three‐component reaction of benzyl alcohol, 1‐phenylethanol and 3‐aminopyrazole for the synthesis of pharmaceutical skeleton pyrazolo[1,5‐a]pyrimidine. The catalytic system can be successfully reused 10 times with a small decrease of its catalytic performance. The catalyst shows extraordinary catalytic activity, high stability, good reusability, and wide applicability to diverse substrates.

show abstract

Section: Introductionmentioning

confidence: 99%

Magnetic Fe₃O₄@Ag nanoparticles catalyzed C–C cross‐coupling reaction of aromatic alcohols

Tang

Feng

Huang

et al. 2022

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…Therefore, heterogeneous catalysts with recyclability have been developed such as supported catalysts. Our group has engaged in developing heterogeneous catalysts for dehydrogenation and hydrogen-borrowing reactions that are recyclable, such as polymer Zr-CIA, 17 POP-Ir, 18 Cu(binap)I] 2 , 19 TTA-Au-NG, 20 NQ-MR, 21 and Au@HT. 22 However, some catalytic systems are effective as catalysts, but demonstrate poor recyclability and stability, for example, catalysts with noble metal cores, such as iridium and gold, while others have reduced catalytic ability after several cycles.…”

Section: Introductionmentioning

confidence: 99%

Silver/manganese dioxide nanorod catalyzed hydrogen-borrowing reactions and tert-butyl ester synthesis

Luo

Yang

et al. 2021

Journal of Chemical Research

Self Cite

View full text Add to dashboard Cite

Silver/manganese dioxide (Ag@MnO2) nanorods are synthesized and characterized by scanning electron microscopy, transmission electron microscopy, energy dispersive X-ray spectroscopy, X-ray powder diffraction, and X-ray photoelectron spectroscopy. It was discovered that Ag@MnO2 nanorods can realize hydrogen-borrowing reactions in high yields and are also effective for the synthesis of tert-butyl esters from aryl cyanides and tert-butyl hydroperoxide in a short period of time. Mechanistic experiments revealed that this catalytic system acts as a Lewis acid in hydrogen-borrowing reactions, while the synthesis of tert-butyl esters occurs through a radical pathway. This is the first report on the excellent catalytic activity of Ag@MnO2 nanorods as a catalyst.

show abstract

“…[33][34][35][36][37][38][39][40][41][42][43][44][45][46][47] From the perspectives of sustainable development and easy recovery, it is clearly necessary to develop a recoverable catalytic system to realize the synthesis of 2-(phenylthio)phenol derivatives with good efficiency and recyclability. Based on our continuing efforts towards sustainable development in dehydrogenation, [48][49][50][51][52][53][54] borrowing hydrogen reactions [55][56][57][58][59] and quinone synthesis, [60][61][62][63][64][65][66] herein, we report that the heterogeneous [Cu(binap)I] 2 complex supported on hydrotalcite can be applied to cascade C─H functionalization with sequential hydroxylation from arylboric acids and thiophenols under mild conditions, leading to 2-sulfanylphenols and arylthioquinones, respectively (Fig. 2).…”

Section: Introductionmentioning

confidence: 99%

The Cascade C─H functionalization with sequential hydroxylation and oxidation through heterogeneous BINAP‐copper on hydrotalcite

Zhang

Wang

et al. 2020

J of Chemical Tech & Biotech

Self Cite

View full text Add to dashboard Cite

BACKGROUND Aromatic thioether derivatives exist widely in natural products and have significant applications in modern synthesis and the pharmaceutical industry; for example, 2‐sulfanylphenols and arylthioquinones are important intermediates in the processing of anticancer, antibiotic, antivirus and antimalarial drugs. Direct C─H hydroxylation was considered as one of the efficient methods for the synthesis of these compounds. Homogeneous transition metal catalysts usually were used through a cross‐coupling of halogen‐substituted phenols with thiophenols. However, from the perspectives of sustainable development and easy recovery, it is necessary to develop an efficient and recoverable catalytic system to realize the synthesis of aromatic thioether derivatives with good efficiency and recyclability. RESULTS The heterogeneous catalyst [Cu(binap)I]2@HT in the present work showed good catalytic activity for the C─H hydroxylation of benzenethiol and phenylboronic acid. The catalytic system was tolerant to various substituents including alkyl, alkoxy, ester, halogen or trifluoromethyl on the phenyl ring of the thiophenols or arylboric acids. In addition to electron‐donating groups, the products with strong electron‐withdrawing groups, such as methyl formylate and trifluoromethyl also were achieved with good yields at 90 °C for 12 h (68% and 66%, respectively). Repeated experiment results showed that the catalyst could be reused at least five times without obvious decrease in catalytic activity. CONCLUSION A BINAP‐Cu complex supported on hydrotalcite was prepared and used as a heterogeneous catalyst for the C─H activation of thiophenol under mild reaction conditions. Through a cascade C─H hydroxylation and further oxidation process, 2‐Sulfanylphenols and arylthioquinones could be obtained with moderate‐to‐good yields for a series of 2‐(phenylthio)phenol derivatives using the heterogeneous catalyst [Cu(binap)I]2@HT. In addition, this heterogeneous catalyst showed good recylbility. © 2020 Society of Chemical Industry

show abstract

Thienylbenzotriazole promoted highly active gold nanoparticles supported on N-doped graphene as efficient catalysts in water and a mechanism exploration

Abstract: Gold nanocomposite catalyzed alkylation of ketone with alcohol, alcohol and alcohol, particularly for amine and amine in water.

Cited by 50 publications

References 89 publications

Magnetic Fe₃O₄@Ag nanoparticles catalyzed C–C cross‐coupling reaction of aromatic alcohols

Magnetic Fe₃O₄@Ag nanoparticles catalyzed C–C cross‐coupling reaction of aromatic alcohols

Silver/manganese dioxide nanorod catalyzed hydrogen-borrowing reactions and tert-butyl ester synthesis

The Cascade C─H functionalization with sequential hydroxylation and oxidation through heterogeneous BINAP‐copper on hydrotalcite

Contact Info

Product

Resources

About

Thienylbenzotriazole promoted highly active gold nanoparticles supported on N-doped graphene as efficient catalysts in water and a mechanism exploration

Abstract: Gold nanocomposite catalyzed alkylation of ketone with alcohol, alcohol and alcohol, particularly for amine and amine in water.

Cited by 50 publications

References 89 publications

Magnetic Fe3O4@Ag nanoparticles catalyzed C–C cross‐coupling reaction of aromatic alcohols

Magnetic Fe3O4@Ag nanoparticles catalyzed C–C cross‐coupling reaction of aromatic alcohols

Silver/manganese dioxide nanorod catalyzed hydrogen-borrowing reactions and tert-butyl ester synthesis

The Cascade C─H functionalization with sequential hydroxylation and oxidation through heterogeneous BINAP‐copper on hydrotalcite

Contact Info

Product

Resources

About

Magnetic Fe₃O₄@Ag nanoparticles catalyzed C–C cross‐coupling reaction of aromatic alcohols

Magnetic Fe₃O₄@Ag nanoparticles catalyzed C–C cross‐coupling reaction of aromatic alcohols