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Molecules
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Metal-Catalyzed Organic Transformations: Expanding Horizons in Synthetic Methodology
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Metal-Catalyzed Organic Transformations: Expanding Horizons in Synthetic Methodology

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: 29 November 2024 | Viewed by 2200

Special Issue Editor

Dr. Chen Chen

E-Mail Website
Guest Editor
College of Chemistry, Tianjin Normal University, Tianjin, China
Interests: palladium catalysis; cyclization reaction; green chemistry; domino reaction; free radical chemistry

Special Issue Information

Dear Colleagues,

Metal-catalyzed organic transformations are crucial tools for synthesizing complex molecules, as they enhance the efficiency of chemical reactions, streamline the synthetic pathways, and reduce the production costs. Therefore, it is essential to develop highly efficient synthetic transformations to construct bioactive molecules using metal catalysis. This Special Issue aims to encompass a comprehensive overview of the latest advancements in metal-catalyzed organic transformations. The Guest Editor invites reviews and original research articles that explore the diverse and expanding horizons of synthetic methodology enabled by metal catalysts. The topics encompass innovative strategies used to construct complex molecules, efficient synthetic pathways, and the synthesis of bioactive compounds. This collection serves as a valuable resource for researchers seeking to stay abreast of the latest developments in metal-catalyzed organic transformations and their impact on synthetic chemistry.

Dr. Chen Chen
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • multicomponent reactions
  • transition metal catalysis
  • organometallic chemistry
  • electrosynthesis
  • photocatalysis
  • green organic synthesis
  • bioactive molecules

Published Papers (4 papers)

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Research

16 pages, 3215 KiB  
Article
P(V)-Promoted Rh-Catalyzed Highly Regioselective Hydroformylation of Styrenes under Mild Conditions
by Tong Ru, Yajiao Zhang, Qiuxiang Wei, Sheng Zuo, Zhenhua Jia and Fen-Er Chen
Molecules 2024, 29(9), 2039; https://doi.org/10.3390/molecules29092039 - 28 Apr 2024
Viewed by 324
Abstract
Hydroformylation of olefins is widely used in the chemical industry due to its versatility and the ability to produce valuable aldehydes with 100% atom economy. Herein, a hybrid phosphate promoter was found to efficiently promote rhodium-catalyzed hydroformylation of styrenes under remarkably mild conditions [...] Read more.
Hydroformylation of olefins is widely used in the chemical industry due to its versatility and the ability to produce valuable aldehydes with 100% atom economy. Herein, a hybrid phosphate promoter was found to efficiently promote rhodium-catalyzed hydroformylation of styrenes under remarkably mild conditions with high regioselectivities. Preliminary mechanistic studies revealed that the weak coordination between the Rhodium and the P=O double bond of this pentavalent phosphate likely induced exceptional reactivity and high ratios of branched aldehydes to linear products. Full article
(This article belongs to the Special Issue Metal-Catalyzed Organic Transformations: Expanding Horizons in Synthetic Methodology)
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13 pages, 1869 KiB  
Communication
Photoinduced Site-Selective Aryl C-H Borylation with Electron-Donor-Acceptor Complex Derived from B2Pin2 and Isoquinoline
by Manhong Li, Yi-Hui Deng, Qianqian Chang, Jinyuan Li, Chao Wang, Leifeng Wang and Tian-Yu Sun
Molecules 2024, 29(8), 1783; https://doi.org/10.3390/molecules29081783 - 14 Apr 2024
Viewed by 623
Abstract
Due to boron’s metalloid properties, aromatic boron reagents are prevalent synthetic intermediates. The direct borylation of aryl C-H bonds for producing aromatic boron compounds offers an appealing, one-step solution. Despite significant advances in this field, achieving regioselective aryl C-H bond borylation using simple [...] Read more.
Due to boron’s metalloid properties, aromatic boron reagents are prevalent synthetic intermediates. The direct borylation of aryl C-H bonds for producing aromatic boron compounds offers an appealing, one-step solution. Despite significant advances in this field, achieving regioselective aryl C-H bond borylation using simple and readily available starting materials still remains a challenge. In this work, we attempted to enhance the reactivity of the electron-donor-acceptor (EDA) complex by selecting different bases to replace the organic base (NEt3) used in our previous research. To our delight, when using NH4HCO3 as the base, we have achieved a mild visible-light-mediated aromatic C-H bond borylation reaction with exceptional regioselectivity (rr > 40:1 to single isomers). Compared with our previous borylation methodologies, this protocol provides a more efficient and broader scope for aryl C-H bond borylation through the use of N-Bromosuccinimide. The protocol’s good functional-group tolerance and excellent regioselectivity enable the functionalization of a variety of biologically relevant compounds and novel cascade transformations. Mechanistic experiments and theoretical calculations conducted in this study have indicated that, for certain arenes, the aryl C-H bond borylation might proceed through a new reaction mechanism, which involves the formation of a novel transient EDA complex. Full article
(This article belongs to the Special Issue Metal-Catalyzed Organic Transformations: Expanding Horizons in Synthetic Methodology)
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16 pages, 2692 KiB  
Article
tert-Butyl Nitrite-Induced Radical Nitrile Oxidation Cycloaddition: Synthesis of Isoxazole/Isoxazoline-Fused Benzo 6/7/8-membered Oxacyclic Ketones
by Jian-Kang Cao, Tian-Zheng Cao, Qian-Wen Yue, Ying Ma, Chuan-Ming Yang, Hong-Xi Zhang, Ya-Chen Li, Qiao-Ke Dong, Yan-Ping Zhu and Yuan-Yuan Sun
Molecules 2024, 29(6), 1202; https://doi.org/10.3390/molecules29061202 - 07 Mar 2024
Viewed by 646
Abstract
A practical metal-free and additive-free approach for the synthesis of 6/7/8-membered oxacyclic ketone-fused isoxazoles/isoxazolines tetracyclic or tricyclic structures is reported through Csp3–H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl methyl ketones. This convenient approach enables the [...] Read more.
A practical metal-free and additive-free approach for the synthesis of 6/7/8-membered oxacyclic ketone-fused isoxazoles/isoxazolines tetracyclic or tricyclic structures is reported through Csp3–H bond radical nitrile oxidation and the intramolecular cycloaddition of alkenyl/alkynyl-substituted aryl methyl ketones. This convenient approach enables the simultaneous formation of isoxazole/isoxazoline and 6/7/8-membered oxacyclic ketones to form polycyclic architectures by using tert-butyl nitrite (TBN) as a non-metallic radical initiator and N–O fragment donor. Full article
(This article belongs to the Special Issue Metal-Catalyzed Organic Transformations: Expanding Horizons in Synthetic Methodology)
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12 pages, 1737 KiB  
Article
Enhanced Selectivity in 4-Quinolone Formation: A Dual-Base System for Palladium-Catalyzed Carbonylative Cyclization with Fe(CO)5
by Meng Guo, Dou Wu, Hongyu Yang, Xiao Zhang, Dong-Xu Xue and Weiqiang Zhang
Molecules 2024, 29(4), 850; https://doi.org/10.3390/molecules29040850 - 14 Feb 2024
Viewed by 419
Abstract
The use of gaseous CO in Pd-catalyzed carbonylative quinolone synthesis presents challenges related to safety and precise pressure control. In response, a streamlined non-gaseous synthesis of 4-quinolone compounds has been developed. This study introduces a tunable CO-releasing system utilizing Fe(CO)5 activated by [...] Read more.
The use of gaseous CO in Pd-catalyzed carbonylative quinolone synthesis presents challenges related to safety and precise pressure control. In response, a streamlined non-gaseous synthesis of 4-quinolone compounds has been developed. This study introduces a tunable CO-releasing system utilizing Fe(CO)5 activated by a dual-base system of piperazine and triethylamine. This alternative liquid CO resource facilitates the palladium-catalyzed carbonylative C-C coupling and subsequent intramolecular cyclization. By tuning the tandem kinetics of carbonylation and cyclization, this non-gaseous method achieves the successful synthesis of 22 distinct 4-quinolones with excellent yields. This is achieved through the three-component condensation of sub-stoichiometric amounts of Fe(CO)5 with 2-iodoaniline and terminal alkynes. Operando mechanistic studies have revealed a novel CO transfer mechanism that facilitates homogeneous carbonylative cyclization, distinguishing this method from traditional techniques. In addition to addressing safety concerns, this approach also provides precise control over selectivity, with significant implications for pharmaceutical research and the efficient synthesis of pharmaceutical and bioactive compounds. Full article
(This article belongs to the Special Issue Metal-Catalyzed Organic Transformations: Expanding Horizons in Synthetic Methodology)
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