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Photoredox Catalysis for Sustainable Chemical Synthesis/Medicinal Chemistry
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Photoredox Catalysis for Sustainable Chemical Synthesis/Medicinal Chemistry

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

Deadline for manuscript submissions: closed (31 May 2022) | Viewed by 31921

Special Issue Editors

Dr. Steven Bloom

E-Mail Website
Guest Editor
Gray Little Hall, Room 2191, University of Kansas1567 Irving Hill Rd, Lawrence, KS 66045-7572, USA
Interests: photoredox catalysis; medicinal chemistry; synthetic chemistry; biotechnology; synthesis of peptide; bioactive compounds
Prof. Dr. Lei Zhou

E-Mail Website
Guest Editor
School of Chemistry, Sun Yat-Sen University, 135 Xingang West Road, Guangzhou 510275, China
Interests: photoredox catalyst; radical; C-F bond cleavage; diazo compound; carbene

Special Issue Information

Dear Colleagues,

Photoredox catalysis has emerged as an attractive tool for organic synthesis and medicinal chemistry. The application of visible light-induced processes can greatly accelerate drug discovery programs and pharmaceutical research, through sustainable and environmentally compatible one-step reactions.

In this Special Issue, “Photoredox Catalysis for Sustainable Chemical Synthesis/Medicinal Chemistry”, we invite papers related to new methodology enabled by photoredox catalysis, development and application of new photocatalysts, natural products and biologically active molecules synthesis using photoredox catalysis, and relevant mechanism studies. We also invite papers that describe new platforms for assessing the bioactivity of lead molecules through photoredox processes, enable structure–activity relationship studies, and facilitate hit-to-lead library development. Papers related to electrophotocatalysis, metallaphotoredox catalysis, photo-organocatalysis, and on-scale photoredox processes for drug discovery are also encouraged.

Dr. Steven Bloom
Prof. Dr. Lei Zhou
Guest Editors

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Keywords

  • visible light
  • photoredox catalysis
  • radical
  • synthesis
  • medicinal chemistry
  • single electron transfer

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Published Papers (6 papers)

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Research

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11 pages, 1409 KiB  
Article
Direct Photoexcitation of Benzothiazolines: Acyl Radical Generation and Application to Access Heterocycles
by Xiang-Kui He, Juan Lu, Hai-Bing Ye, Lei Li and Jun Xuan
Molecules 2021, 26(22), 6843; https://doi.org/10.3390/molecules26226843 - 12 Nov 2021
Cited by 9 | Viewed by 3617
Abstract
An acyl radical generation and functionalization strategy through direct photoexcitation of benzothiazolines has been developed. The formed acyl radical species can either be trapped by quinoxalin-2-ones to realize their C(3)-H functionalization or trigger a cascade radical cyclization with isonitriles to synthesise biologically important [...] Read more.
An acyl radical generation and functionalization strategy through direct photoexcitation of benzothiazolines has been developed. The formed acyl radical species can either be trapped by quinoxalin-2-ones to realize their C(3)-H functionalization or trigger a cascade radical cyclization with isonitriles to synthesise biologically important phenanthridines. The synthetic value of this protocol can be further illustrated by the modification of quinoxalin-2-ones, containing important natural products and drug-based complex molecules. Full article
(This article belongs to the Special Issue Photoredox Catalysis for Sustainable Chemical Synthesis/Medicinal Chemistry)
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Review

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22 pages, 4883 KiB  
Review
Recent Advances in Visible-Light Photoredox Catalysis for the Thiol-Ene/Yne Reactions
by Qian Xiao, Qing-Xiao Tong and Jian-Ji Zhong
Molecules 2022, 27(3), 619; https://doi.org/10.3390/molecules27030619 - 18 Jan 2022
Cited by 37 | Viewed by 4619
Abstract
Visible-light photoredox catalysis has been established as a popular and powerful tool for organic transformations owing to its inherent characterization of environmental friendliness and sustainability in the past decades. The thiol-ene/yne reactions, the direct hydrothiolation of alkenes/alkynes with thiols, represents one of the [...] Read more.
Visible-light photoredox catalysis has been established as a popular and powerful tool for organic transformations owing to its inherent characterization of environmental friendliness and sustainability in the past decades. The thiol-ene/yne reactions, the direct hydrothiolation of alkenes/alkynes with thiols, represents one of the most efficient and atom-economic approaches for the carbon-sulfur bonds construction. In traditional methodologies, harsh conditions such as stoichiometric reagents or a specialized UV photo-apparatus were necessary suffering from various disadvantages. In particular, visible-light photoredox catalysis has also been demonstrated to be a greener and milder protocol for the thiol-ene/yne reactions in recent years. Additionally, unprecedented advancements have been achieved in this area during the past decade. In this review, we will summarize the recent advances in visible-light photoredox catalyzed thiol-ene/yne reactions from 2015 to 2021. Synthetic strategies, substrate scope, and proposed reaction pathways are mainly discussed. Full article
(This article belongs to the Special Issue Photoredox Catalysis for Sustainable Chemical Synthesis/Medicinal Chemistry)
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41 pages, 8304 KiB  
Review
Recent Advances in Visible-Light-Mediated Amide Synthesis
by Bin Lu, Wen-Jing Xiao and Jia-Rong Chen
Molecules 2022, 27(2), 517; https://doi.org/10.3390/molecules27020517 - 14 Jan 2022
Cited by 37 | Viewed by 6618
Abstract
Visible-light photoredox catalysis has attracted tremendous interest within the synthetic community. As such, the activation mode potentially provides a more sustainable and efficient platform for the activation of organic molecules, enabling the invention of many controlled radical-involved reactions under mild conditions. In this [...] Read more.
Visible-light photoredox catalysis has attracted tremendous interest within the synthetic community. As such, the activation mode potentially provides a more sustainable and efficient platform for the activation of organic molecules, enabling the invention of many controlled radical-involved reactions under mild conditions. In this context, amide synthesis via the strategy of photoredox catalysis has received growing interest due to the ubiquitous presence of this structural motif in numerous natural products, pharmaceuticals and functionalized materials. Employing this strategy, a wide variety of amides can be prepared effectively from halides, arenes and even alkanes under irradiation of visible light. These methods provide a robust alternative to well-established strategies for amide synthesis that involve condensation between a carboxylic acid and amine mediated by a stoichiometric activating agent. In this review, the representative progresses made on the synthesis of amides through visible light-mediated radical reactions are summarized. Full article
(This article belongs to the Special Issue Photoredox Catalysis for Sustainable Chemical Synthesis/Medicinal Chemistry)
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36 pages, 48366 KiB  
Review
Construction of Chiral Cyclic Compounds Enabled by Enantioselective Photocatalysis
by Bo Xu, Xiaotian Shi, Xiang Liu and Hua Cao
Molecules 2022, 27(2), 359; https://doi.org/10.3390/molecules27020359 - 7 Jan 2022
Cited by 3 | Viewed by 2991
Abstract
Chiral cyclic molecules are some of the most important compounds in nature, and are widely used in the fields of drugs, materials, synthesis, etc. Enantioselective photocatalysis has become a powerful tool for organic synthesis of chiral cyclic molecules. Herein, this review summarized the [...] Read more.
Chiral cyclic molecules are some of the most important compounds in nature, and are widely used in the fields of drugs, materials, synthesis, etc. Enantioselective photocatalysis has become a powerful tool for organic synthesis of chiral cyclic molecules. Herein, this review summarized the research progress in the synthesis of chiral cyclic compounds by photocatalytic cycloaddition reaction in the past 5 years, and expounded the reaction conditions, characters, and corresponding proposed mechanism, hoping to guide and promote the development of this field. Full article
(This article belongs to the Special Issue Photoredox Catalysis for Sustainable Chemical Synthesis/Medicinal Chemistry)
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44 pages, 12973 KiB  
Review
Visible-Light-Induced Catalytic Selective Halogenation with Photocatalyst
by Truong Giang Luu, Yongju Jung and Hee-Kwon Kim
Molecules 2021, 26(23), 7380; https://doi.org/10.3390/molecules26237380 - 5 Dec 2021
Cited by 21 | Viewed by 5385
Abstract
Halide moieties are essential structures of compounds in organic chemistry due to their popularity and wide applications in many fields such as natural compounds, agrochemicals, and pharmaceuticals. Thus, many methods have been developed to introduce halides into various organic molecules. Recently, visible-light-driven reactions [...] Read more.
Halide moieties are essential structures of compounds in organic chemistry due to their popularity and wide applications in many fields such as natural compounds, agrochemicals, and pharmaceuticals. Thus, many methods have been developed to introduce halides into various organic molecules. Recently, visible-light-driven reactions have emerged as useful methods of organic synthesis. Particularly, halogenation strategies using visible light have significantly improved the reaction efficiency and reduced toxicity, as well as promoted reactions under mild conditions. In this review, we have summarized recent studies in visible-light-mediated halogenation (chlorination, bromination, and iodination) with photocatalysts. Full article
(This article belongs to the Special Issue Photoredox Catalysis for Sustainable Chemical Synthesis/Medicinal Chemistry)
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33 pages, 18376 KiB  
Review
Recent Advances in C-F Bond Cleavage Enabled by Visible Light Photoredox Catalysis
by Lei Zhou
Molecules 2021, 26(22), 7051; https://doi.org/10.3390/molecules26227051 - 22 Nov 2021
Cited by 49 | Viewed by 7286
Abstract
The creation of new bonds via C-F bond cleavage of readily available per- or oligofluorinated compounds has received growing interest. Using such a strategy, a myriad of valuable partially fluorinated products can be prepared, which otherwise are difficult to make by the conventional [...] Read more.
The creation of new bonds via C-F bond cleavage of readily available per- or oligofluorinated compounds has received growing interest. Using such a strategy, a myriad of valuable partially fluorinated products can be prepared, which otherwise are difficult to make by the conventional C-F bond formation methods. Visible light photoredox catalysis has been proven as an important and powerful tool for defluorinative reactions due to its mild, easy to handle, and environmentally benign characteristics. Compared to the classical C-F activation that proceeds via two-electron processes, radicals are the key intermediates using visible light photoredox catalysis, providing new modes for the cleavage of C-F bonds. In this review, a summary of the visible light-promoted C-F bond cleavage since 2018 was presented. The contents were classified by the fluorosubstrates, including polyfluorinated arenes, gem-difluoroalkenes, trifluoromethyl arenes, and trifluoromethyl alkenes. An emphasis is placed on the discussion of the mechanisms and limitations of these reactions. Finally, my personal perspective on the future development of this rapidly emerging field was provided. Full article
(This article belongs to the Special Issue Photoredox Catalysis for Sustainable Chemical Synthesis/Medicinal Chemistry)
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