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Molecules
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New Insights in Photoredox Catalysis
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New Insights in Photoredox Catalysis

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

Deadline for manuscript submissions: closed (30 April 2020) | Viewed by 23574

Special Issue Editor

Prof. Dr. Yasuharu Yoshimi

E-Mail Website
Guest Editor
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, University of Fukui, Fukui 910-8507, Japan
Interests: organic photochemistry (synthetic); photoredox catalysis; photoinduced electron transfer; photoinduced decarboxylation
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Photoredox catalysis is currently one of the most significant research topics in chemistry, because photoinduced electron transfer (PET) with organic substrates can provide unique processes for organic synthesis, polymer synthesis, modification of materials, fluorescence sensors, etc. In addition, the photochemical method represents a less toxic and milder process than conventional methods, because light is a clean and traceless reagent. Therefore, this Special Issue aims to illustrate the recent developments in the uses of photoinduced redox processes with organic molecules. The contributions will focus on a broad range of organic reactions by effective homogeneous and heterogeneous photoredox catalysts, as well as on their involvement in the polymer synthesis or modification of materials or fluorescence sensors.

Communications, full papers and reviews on the abovementioned topics are particularly welcome.

Prof. Yasuharu Yoshimi
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

  • Photoredox Catalysis
  • Photoredox Reaction
  • Photoredox Catalyst
  • Photoinduced Electron Transfer
  • Photoinduced Reaction
  • Photoinduced Oxidation
  • Photoinduced Reduction
  • Photochemical Reaction
  • Photoinduced Polymerization
  • Fluorescence Sensor

Published Papers (5 papers)

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Research

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10 pages, 1285 KiB  
Article
Continuous Flow Photochemical and Thermal Multi-Step Synthesis of Bioactive 3-Arylmethylene-2,3-Dihydro-1H-Isoindolin-1-Ones
by Saira Mumtaz, Mark J. Robertson and Michael Oelgemöller
Molecules 2019, 24(24), 4527; https://doi.org/10.3390/molecules24244527 - 11 Dec 2019
Cited by 8 | Viewed by 2724
Abstract
An effective multi-step continuous flow approach towards N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones, including the local anesthetic compound AL-12, has been realized. Compared to the traditional decoupled batch processes, the combined photochemical–thermal–thermal flow setup rapidly provides the desired target compounds in superior yields and [...] Read more.
An effective multi-step continuous flow approach towards N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones, including the local anesthetic compound AL-12, has been realized. Compared to the traditional decoupled batch processes, the combined photochemical–thermal–thermal flow setup rapidly provides the desired target compounds in superior yields and significantly shorter reaction times. Full article
(This article belongs to the Special Issue New Insights in Photoredox Catalysis)
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12 pages, 2879 KiB  
Article
Photoinduced Electron Transfer-Promoted Reactions Using Exciplex-Type Organic Photoredox Catalyst Directly Linking Donor and Acceptor Arenes
by Mugen Yamawaki, Akiko Asano, Toshiki Furutani, Yuki Izumi, Yosuke Tanaka, Kazuyuki Osaka, Toshio Morita and Yasuharu Yoshimi
Molecules 2019, 24(24), 4453; https://doi.org/10.3390/molecules24244453 - 05 Dec 2019
Cited by 2 | Viewed by 3426
Abstract
Directly linked donor and acceptor arenes, such as phenanthrene/naphthalene/biphenyl and 1,3-dicyanobenzene were found to work as photoredox catalysts in the photoreactions of indene, 2,3-dimethyl-2-butene, and 4-methoxyphenylacetic acid. The new stable organic photocatalyst forms an intramolecular exciplex (excited complex) when irradiated in a polar [...] Read more.
Directly linked donor and acceptor arenes, such as phenanthrene/naphthalene/biphenyl and 1,3-dicyanobenzene were found to work as photoredox catalysts in the photoreactions of indene, 2,3-dimethyl-2-butene, and 4-methoxyphenylacetic acid. The new stable organic photocatalyst forms an intramolecular exciplex (excited complex) when irradiated in a polar solvent and shows redox catalyst activity, even at low concentrations. To the best of our knowledge, this is the first example of an intramolecular exciplex working as a redox catalyst. Full article
(This article belongs to the Special Issue New Insights in Photoredox Catalysis)
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11 pages, 3591 KiB  
Article
Enantioselective Protonation of Radical Anion Intermediates in Photoallylation and Photoreduction Reactions of 3,3-Diaryl-1,1-dicyano-2-methylprop-1-ene with Allyltrimethylsilane
by Hajime Maeda, Masayuki Iida, Daisuke Ogawa and Kazuhiko Mizuno
Molecules 2019, 24(14), 2677; https://doi.org/10.3390/molecules24142677 - 23 Jul 2019
Cited by 1 | Viewed by 3463
Abstract
Photoreactions of acetonitrile solutions of 3,3-diaryl-1,1-dicyano-2-methylprop-1-enes (1a–c) with allyltrimethylsilane (2) in the presence of phenanthrene as a photoredox catalyst and acetic acid as a proton source formed photoallylation (3) and photoreduction (4) products [...] Read more.
Photoreactions of acetonitrile solutions of 3,3-diaryl-1,1-dicyano-2-methylprop-1-enes (1a–c) with allyltrimethylsilane (2) in the presence of phenanthrene as a photoredox catalyst and acetic acid as a proton source formed photoallylation (3) and photoreduction (4) products via photoinduced electron transfer pathways. When (S)-mandelic acid was used as the proton source, the reactions proceeded with 3.4 and 4.8 %ee for formation of 3 and 4, respectively. The results of studies of the effect of aryl ring substituents and several chiral carboxylic acids suggested that the enantioselectivities of the reactions are governed by steric controlled proton transfer in intermediate complexes formed by π-π and OH-π interactions of anion radicals derived from 1a–c and chiral carboxylic acids. Full article
(This article belongs to the Special Issue New Insights in Photoredox Catalysis)
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Review

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22 pages, 10103 KiB  
Review
Recent Advances in Enantioselective Photochemical Reactions of Stabilized Diazo Compounds
by Ting-Bi Hua, Qing-Qing Yang and You-Quan Zou
Molecules 2019, 24(17), 3191; https://doi.org/10.3390/molecules24173191 - 02 Sep 2019
Cited by 36 | Viewed by 5857
Abstract
Diazo compounds have proven to be a useful class of carbenes or metal carbenoids sources under thermal, photochemical, or metal-catalyzed conditions, which can subsequently undergo a wide range of synthetically important transformations. Recently, asymmetric photocatalysis has provoked increasing research interests, and great advances [...] Read more.
Diazo compounds have proven to be a useful class of carbenes or metal carbenoids sources under thermal, photochemical, or metal-catalyzed conditions, which can subsequently undergo a wide range of synthetically important transformations. Recently, asymmetric photocatalysis has provoked increasing research interests, and great advances have been made in this discipline towards the synthesis of optically enriched compounds. In this context, the past two decades have been the most productive period in the developments of enantioselective photochemical reactions of diazo compounds due to a better understanding of the reactivities of diazo compounds and the emergence of new catalytic modes, as well as easier access to and treatment of stabilized diazo compounds. This review highlights these impressive achievements according to the reaction type, and the general mechanisms and stereochemical inductions are briefly discussed as well. Full article
(This article belongs to the Special Issue New Insights in Photoredox Catalysis)
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22 pages, 9721 KiB  
Review
TiO2 Photocatalysis for Transfer Hydrogenation
by Dongge Ma, Shan Zhai, Yi Wang, Anan Liu and Chuncheng Chen
Molecules 2019, 24(2), 330; https://doi.org/10.3390/molecules24020330 - 17 Jan 2019
Cited by 48 | Viewed by 7565
Abstract
Catalytic transfer hydrogenation reactions, based on hydrogen sources other than gaseous H2, are important processes that are preferential in both laboratories and factories. However, harsh conditions, such as high temperature, are usually required for most transition-metal catalytic and organocatalytic systems. Moreover, [...] Read more.
Catalytic transfer hydrogenation reactions, based on hydrogen sources other than gaseous H2, are important processes that are preferential in both laboratories and factories. However, harsh conditions, such as high temperature, are usually required for most transition-metal catalytic and organocatalytic systems. Moreover, non-volatile hydrogen donors such as dihydropyridinedicarboxylate and formic acid are often required in these processes which increase the difficulty in separating products and lowered the whole atom economy. Recently, TiO2 photocatalysis provides mild and facile access for transfer hydrogenation of C=C, C=O, N=O and C-X bonds by using volatile alcohols and amines as hydrogen sources. Upon light excitation, TiO2 photo-induced holes have the ability to oxidatively take two hydrogen atoms off alcohols and amines under room temperature. Simultaneously, photo-induced conduction band electrons would combine with these two hydrogen atoms and smoothly hydrogenate multiple bonds and/or C-X bonds. It is heartening that practices and principles in the transfer hydrogenations of substrates containing C=C, C=O, N=O and C-X bond based on TiO2 photocatalysis have overcome a lot of the traditional thermocatalysis’ limitations and flaws which usually originate from high temperature operations. In this review, we will introduce the recent paragon examples of TiO2 photocatalytic transfer hydrogenations used in (1) C=C and C≡C (2) C=O and C=N (3) N=O substrates and in-depth discuss basic principle, status, challenges and future directions of transfer hydrogenation mediated by TiO2 photocatalysis. Full article
(This article belongs to the Special Issue New Insights in Photoredox Catalysis)
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