Dataset Information

Electrochemical Access to Aza-Polycyclic Aromatic Hydrocarbons: Rhoda-Electrocatalyzed Domino Alkyne Annulations.

ABSTRACT: Nitrogen-doped polycyclic aromatic hydrocarbons (aza-PAHs) have found broad applications in material sciences. Herein, a modular electrochemical synthesis of aza-PAHs was developed via a rhodium-catalyzed cascade C-H activation and alkyne annulation. A multifunctional O-methylamidoxime enabled the high chemo- and regioselectivity. The isolation of two key rhodacyclic intermediates made it possible to delineate the exact order of three C-H activation steps. In addition, the metalla-electrocatalyzed multiple C-H transformation is characterized by unique functional group tolerance, including highly reactive iodo and azido groups.

SUBMITTER: Kong WJ

PROVIDER: S-EPMC7155118 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Publications

Electrochemical Access to Aza-Polycyclic Aromatic Hydrocarbons: Rhoda-Electrocatalyzed Domino Alkyne Annulations.

Kong Wei-Jun WJ Shen Zhigao Z Finger Lars H LH Ackermann Lutz L

Angewandte Chemie (International ed. in English) 20200128 14

Nitrogen-doped polycyclic aromatic hydrocarbons (aza-PAHs) have found broad applications in material sciences. Herein, a modular electrochemical synthesis of aza-PAHs was developed via a rhodium-catalyzed cascade C-H activation and alkyne annulation. A multifunctional O-methylamidoxime enabled the high chemo- and regioselectivity. The isolation of two key rhodacyclic intermediates made it possible to delineate the exact order of three C-H activation steps. In addition, the metalla-electrocatalyz ...[more]

PMID: 31793169

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Project description:Polycyclic aromatic hydrocarbons (PAHs), especially high molecular weight PAHs, are carcinogenic and mutagenic organic compounds that are difficult to degrade. Microbial remediation is a popular method for the PAH removal in diverse environments and yet it is limited by the lack of electron acceptors. An emerging solution is to use the microbial electrochemical system, in which the solid anode is used as an inexhaustible electron acceptor and the microbial activity is stimulated by biocurrent in situ to ensure the PAH removal and avoid the defects of bioremediation. Based on the extensive investigation of recent literatures, this paper summarizes and comments on the research progress of PAH removal by the microbial electrochemical system of diversified design, enhanced measures and functional microorganisms. First, the bioelectrochemical degradation of PAHs is reviewed in separate and mixed PAH degradation, and the removal performance of PAHs in different system configurations is compared with the anode modification, the enhancement of substrate and electron transfer, the addition of chemical reagents, and the combination with phytoremediation. Second, the key functional microbiota including PAH degrading microbes and exoelectrogens are overviewed as well as the reduced microbes without competitive advantage. Finally, the typical representations of electrochemical activity especially the internal resistance, power density and current density of systems and influence factors are reviewed with the correlation analysis between PAH removal and energy generation. Presently, most studies focused on the anode modification in the bioelectrochemical degradation of PAHs and actually more attentions need to be paid to enhance the mass transfer and thus larger remediation radius, and other smart designs are also proposed, especially that the combined use of phytoremediation could be an eco-friendly and sustainable approach. Additionally, exoelectrogens and PAH degraders are partially overlapping, but the exact functional mechanisms of interaction network are still elusive, which could be revealed with the aid of advanced bioinformatics technology. In order to optimize the efficacy of functional community, more advanced techniques such as omics technology, photoelectrocatalysis and nanotechnology should be considered in the future research to improve the energy generation and PAH biodegradation rate simultaneously.

Dataset Information

Electrochemical Access to Aza-Polycyclic Aromatic Hydrocarbons: Rhoda-Electrocatalyzed Domino Alkyne Annulations.

Publications

Electrochemical Access to Aza-Polycyclic Aromatic Hydrocarbons: Rhoda-Electrocatalyzed Domino Alkyne Annulations.

Similar Datasets

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