Catalyzed Carbon-Heteroatom Bond Formation

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalysis in Organic and Polymer Chemistry".

Deadline for manuscript submissions: closed (30 November 2023) | Viewed by 9005

Special Issue Editors


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Guest Editor
Jiangxi Provincial Key Laboratory of Functional Molecular Materials Chemistry, Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, Ganzhou 341000, China
Interests: organic synthesis; drug synthesis; fluorescent probes
Special Issues, Collections and Topics in MDPI journals

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Guest Editor
Jiangxi Provincial Key Laboratory of Functional Molecular Materials Chemistry, Faculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, Ganzhou, China
Interests: coupling reaction; free-radical reaction; green chemistry; fluorescence probe based on organic reaction; transition-metal catalysis

Special Issue Information

Dear Colleagues,

While the backbone of organic molecules mainly consists of C–C bonds, their function is often derived from the presence of heteroatoms. Almost all natural products, pharmaceuticals, agrochemicals, and polymeric materials contain carbon–heteroatom bonds, which are often introduced by synthetic chemists through small-molecule organocatalytic, transition-metal catalytic, photocatalytic, and electrocatalytic carbon–heteroatom bond formation. The resurgence of catalytic chemistry has resulted in a series of C–heteroatom bond formations that are complementary to traditional transformations.

This Special Issue aims to collect original research papers or reviews dealing with organocatalytic, transition-metal catalytic, photocatalytic, and electrocatalytic carbon–heteroatom bond formation. Manuscripts concerning fluorescent probes based on catalytic reactions are also welcome.

We look forward to receiving your contributions.

Dr. Jinbiao Liu
Dr. Kunming Liu
Guest Editors

Manuscript Submission Information

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Keywords

  • small-molecule organocatalysis
  • transition-metal catalysis
  • photocatalysis
  • electrocatalysis
  • carbon–heteroatom bond formation
  • fluorescent probe based on catalytic reaction

Published Papers (4 papers)

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Research

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13 pages, 1745 KiB  
Article
Copper-Catalyzed N-Arylation of Pyranoquinolinones with Boronic Acids at Room Temperature without Ligand
by Wei Gao, Fang Gao, Haikuan Yang, Zongde Wang and Yaru Huang
Catalysts 2023, 13(7), 1060; https://doi.org/10.3390/catal13071060 - 30 Jun 2023
Cited by 1 | Viewed by 931
Abstract
Pyranoquinolinones synthesized from citral were used for Cu-catalyzed N-arylation with a wide range of arylboric acids. The reaction proceeded well with a broad substrate scope, providing a direct way to access highly functional pyranoquinolinone core structure derivatives in yields of up to [...] Read more.
Pyranoquinolinones synthesized from citral were used for Cu-catalyzed N-arylation with a wide range of arylboric acids. The reaction proceeded well with a broad substrate scope, providing a direct way to access highly functional pyranoquinolinone core structure derivatives in yields of up to 80%. Compared to citral, the compounds we obtained have a much better inhibitory effect on HeLa cervical cancer cells, and compound 3p has an IC50 value of 4.6 μM, lower than cisplatin’s 5.9 μM. Full article
(This article belongs to the Special Issue Catalyzed Carbon-Heteroatom Bond Formation)
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12 pages, 1277 KiB  
Article
Photocatalytic Synthesis of 6-Phosphorylated Phenanthridines from 2-Isocyanobiphenyls via Radical C−P and C−C Bond Formation
by Liping Wang, Qin Zhang, Xiaoyan Sang and Qiuping Ding
Catalysts 2023, 13(7), 1036; https://doi.org/10.3390/catal13071036 - 25 Jun 2023
Cited by 1 | Viewed by 698
Abstract
A mild, efficient, photocatalytic synthesis of 6-phosphorylated phenanthridines via tandem radical addition/cyclization/aromatization of 2-isocyanobiphenyls with diarylphosphine oxides is reported. The method features operational simplicity in metal-free conditions, using low-cost Rose Bengal as a catalyst and sustainable air as a terminal oxidant at room [...] Read more.
A mild, efficient, photocatalytic synthesis of 6-phosphorylated phenanthridines via tandem radical addition/cyclization/aromatization of 2-isocyanobiphenyls with diarylphosphine oxides is reported. The method features operational simplicity in metal-free conditions, using low-cost Rose Bengal as a catalyst and sustainable air as a terminal oxidant at room temperature and providing the desired products in moderate to good yields. Full article
(This article belongs to the Special Issue Catalyzed Carbon-Heteroatom Bond Formation)
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10 pages, 2270 KiB  
Article
Selective C-O Coupling Reaction of N-Methoxy Arylamides and Arylboronic Acids Catalyzed by Copper Salt
by Ying Wang, Huilin Xie, Kunming Liu, Jinhui Li and Jin-Biao Liu
Catalysts 2022, 12(10), 1278; https://doi.org/10.3390/catal12101278 - 19 Oct 2022
Cited by 3 | Viewed by 1652
Abstract
Herein, we report a copper-catalyzed C-O cross-coupling of N-methoxy amides and arylboronic acids for the synthesis of aryl-N-methoxy arylimides. The fully selective O-arylation of the N-methoxy amides is found to be greatly prompted by the inexpensive and commercially available CuI. The reaction conditions [...] Read more.
Herein, we report a copper-catalyzed C-O cross-coupling of N-methoxy amides and arylboronic acids for the synthesis of aryl-N-methoxy arylimides. The fully selective O-arylation of the N-methoxy amides is found to be greatly prompted by the inexpensive and commercially available CuI. The reaction conditions tolerate a variety of functional groups and promote different reactivities depending on the electronic and steric properties of the distorted substrates. Full article
(This article belongs to the Special Issue Catalyzed Carbon-Heteroatom Bond Formation)
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Review

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24 pages, 8329 KiB  
Review
Advances in the Application of Acetonitrile in Organic Synthesis since 2018
by Pinyong Zhong, Linjun Zhang, Nianhua Luo and Jinbiao Liu
Catalysts 2023, 13(4), 761; https://doi.org/10.3390/catal13040761 - 16 Apr 2023
Cited by 5 | Viewed by 5050
Abstract
Acetonitrile is commonly used as an organic solvent and can also be used as an important intermediate in organic synthesis. Its widespread use has led to the development of new methods for the synthesis of a variety of important compounds. In the past [...] Read more.
Acetonitrile is commonly used as an organic solvent and can also be used as an important intermediate in organic synthesis. Its widespread use has led to the development of new methods for the synthesis of a variety of important compounds. In the past decades, the conversion reactions of acetonitrile as a building block have become one of the most-attractive fields in organic synthesis. Especially in the field of electrochemical conversions involving acetonitrile, due to its good conductivity and environmentally friendly features, it has become a powerful and compelling tool to afford nitrogen-containing compounds or nitrile-containing compounds. In this review, we mainly discuss the research progress involving acetonitrile in the past five years, covering both conventional synthesis methods and electrochemical synthesis. Besides, a detailed discussion of the substrate scope and mechanistic pathways is provided. Full article
(This article belongs to the Special Issue Catalyzed Carbon-Heteroatom Bond Formation)
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