Recent Progress in the Research of the Transition-Metal-Catalyzed N-Directed Carbonyl and Alcohol Hydroxyl ortho C-C Bonds Activation Reactions

王晶晶,; 李峰,; 于晓波,; 刘澜涛,; 丁俊汝,; 谢佩瑶,; 王建辉,

doi:10.6023/cjoc201802007

Chin. J. Org. Chem.

2018

DOI: 10.6023/cjoc201802007

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Recent Progress in the Research of the Transition-Metal-Catalyzed N-Directed Carbonyl and Alcohol Hydroxyl ortho C-C Bonds Activation Reactions

王晶晶王晶晶¹,

李峰李峰²,

于晓波于晓波³

et al.

Abstract: Transition-metal-catalyzed C-C bond cleavage has been considered as one of the most interesting subject and challenging area in organometallic chemistry. The recent progress of transition-metal-catalyzed (Rh, Ni, Pd and Ru) nitrogen atom chelation-assisted C-C activation and controlled transformation is reviewed, and the mechanisms of these C-C activation reactions are also discussed.

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Cited by 7 publications

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New chelating N‐heterocyclic carbene palladium complexes immobilized on magnetic nanoparticles: Synthesis, characterization, and catalytic properties

Yang,

Liu,

Diao

et al. 2024

Applied Organom Chemis

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Two chelating N‐heterocyclic carbene (NHC) palladium complexes 3a‐b containing N‐(3‐bromopropyl)‐N′‐thioether difunctionalized imidazol‐2‐ylidene were synthesized by direct metalation of the precursor imidazolium salts and characterized by NMR and HR‐MS. The molecular structure of 3a has been further characterized unambiguously by X‐ray single crystal analysis. The subsequent substitution reaction with amine‐functionalized magnetic nanoparticles (MNPs‐NH2) afforded two highly active, stable, and recyclable magnetic nanoparticle supported NHC palladium complexes, MNPs‐NHC‐Pd I‐II, which were characterized by Fourier transform infrared spectroscopy (FT‐IR), X‐ray diffraction (XRD), inductively coupled plasma optical emission spectrometry (ICP‐OES), scanning electron microscopy (SEM), and X‐ray photoelectron spectroscopy (XPS). The MNPs‐NHC‐Pd complexes exhibited high catalytic activity in the Suzuki–Miyaura cross‐coupling reaction of aryl bromides with arylboronic acids, as well as in the reduction of toxic 4‐nitrophenol (4‐NP) under mild conditions. The recycling experiment of MNPs‐NHC‐Pd I in the Suzuki–Miyaura cross‐coupling reaction between 4‐bromoanisole and phenylboronic acid showed that the yield of 4‐methoxybiphenyl remained high at 88% within 0.5 h at 60 °C, indicating that the catalytic activity was well maintained for at least 10 cycles.

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New chelating N‐heterocyclic carbene palladium complexes immobilized on magnetic nanoparticles: Synthesis, characterization, and catalytic properties

Yang,

Liu,

Diao

et al. 2024

Applied Organom Chemis

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Transition‐Metal‐Catalyzed Carbon‐Carbon Bond Activation in Asymmetric Synthesis

Zhang

2021

Chin. J. Chem.

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Carbon-carbon activation | Transition-metal | Asymmetric catalysis | Asymmetric synthesis | Ring-opening reaction Catalytic asymmetric transformations involving carbon-carbon bond cleavages open intriguing strategies for the synthesis of chiral complex molecules. The transient organometallic species mainly generate from the oxidative addition of cyclic compounds with low valence metals or from β-carbon elimination of tert-alkoxyl metals. This overview covers the recent advances in transition-metal-catalyzed carbon-carbon bond activation in asymmetric synthesis. Xiufen Bi (left) was born in Anhui, China. She obtained her bachelor degree from Anhui Normal University in 2017. Then she turned to University of Science and Technology of China (USTC) to pursue her PhD degree of organic chemistry under the supervision of Professor Gu. Qiuchi Zhang (middle) was born in Sichuan, China. He received his bachelor degree from USTC in 2014. Then he turned to Nanyang Technological University for his doctoral studies and received PhD degree in 2019 under the supervision of Prof. Tech-Peng Loh. He is currently a post-doctor in Prof. Gu's group at USTC. Zhenhua Gu (right) studied chemistry at Nanjing University and received his PhD degree in Shanghai Institute of Organic Chemistry in 2007 with Prof. Shengming Ma. He conducted his postdoctoral research at University of California Berkeley and University of California at Santa Barbara. In 2012, he began his independent academic career at the USTC with the support of "Thousand Talents Plan". Research in his group is mainly focused on the development of new methods for asymmetric atropisomers and their related natural products synthesis.

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Study on the inhibition effect of citric acid on coal spontaneous combustion

Liu

Zhang

et al. 2022

Fuel

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Recent Progress in the Research of the Transition-Metal-Catalyzed N-Directed Carbonyl and Alcohol Hydroxyl ortho C-C Bonds Activation Reactions

Cited by 7 publications

References 1 publication

New chelating N‐heterocyclic carbene palladium complexes immobilized on magnetic nanoparticles: Synthesis, characterization, and catalytic properties

New chelating N‐heterocyclic carbene palladium complexes immobilized on magnetic nanoparticles: Synthesis, characterization, and catalytic properties

Transition‐Metal‐Catalyzed Carbon‐Carbon Bond Activation in Asymmetric Synthesis

Study on the inhibition effect of citric acid on coal spontaneous combustion

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