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Search for "visible-light" in Full Text gives 256 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Oxetanes: formation, reactivity and total syntheses of natural products

  • Peter Gabko,
  • Martin Kalník and
  • Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

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  • performing the reaction under visible light irradiation, or coupling the reaction to other light-induced processes to produce new classes of products. In 2018, Aitken and co-workers reported a synthesis of previously unknown tricyclic 4:4:4 oxetanes 73 through a photochemical triple cascade reaction starting
  • , γ-H transfer and Paternò–Büchi reaction. In 2020, two highly similar methodologies based on a visible-light-mediated Paternò–Büchi reaction between simple alkenes 77 and α-ketoesters 78 were reported independently and shortly after one another (Scheme 21) [61][62]. They both use blue light for
  • promoted by visible light at room temperature, requires no protecting atmosphere or additives, and the resulting polysubstituted oxetanes are obtained in moderate to good yields. Additional advantages include scalability and high chemoselectivity as various functional groups were tolerated, including
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Published 27 Jun 2025

Recent advances in amidyl radical-mediated photocatalytic direct intermolecular hydrogen atom transfer

  • Hao-Sen Wang,
  • Lin Li,
  • Xin Chen,
  • Jian-Li Wu,
  • Kai Sun,
  • Xiao-Lan Chen,
  • Ling-Bo Qu and
  • Bing Yu

Beilstein J. Org. Chem. 2025, 21, 1306–1323, doi:10.3762/bjoc.21.100

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  • modified. In recent years, photocatalysis has been widely adopted due to its green and efficient nature [45][46][47][48][49][50][51]. The generation of amidyl radical is implemented by HRP. Six different methods (Figure 2c), which have been developed for visible-light mediated reactions, could generate
  • (SET) process by the cleavage of the N–O bond; (c) direct homolytic cleavage of weak N–S or N–X bonds in HRP initiated in the presence of visible light; (d) the intersystem crossing (ISC) of S1 to T1 state directly from the amide anion. This review is organized by bond cleavage type, offering a deep
  • demonstrated the homolytic cleavage of the N–O bond using N-(tert-butyl)-O-(1-phenylvinyl)-phenylhydroxyamide as a HAT reagent [78][79]. This compound was capable of initiating the formation of amidyl radicals through visible light activation. Although their controlled experiments showed that this method was
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Published 27 Jun 2025

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

  • Jiangfei Chen,
  • Yi-Lin Qu,
  • Ming Yuan,
  • Xiang-Mei Wu,
  • Heng-Pei Jiang,
  • Ying Fu and
  • Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

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  • quinolinone products. Beyond electrochemical protocols, photochemical activation – particularly visible-light photoredox catalysis – has become a powerful and sustainable strategy for generating carbon radicals under mild conditions. In 2023, Fan’s group discovered a radical cyclization of N-arylacrylamides
  • radical then reacts with acrylamide to yield the desired product 37. As shown in Scheme 21, a visible light-induced trifluoromethylation/arylation using Umemoto’s reagent for the synthesis of trifluoromethylated oxindole derivatives was reported by Huang and Zhang’s group in 2021 [13]. This method is
  • ), the process involves the homolytic cleavage of Umemoto's reagent 39 under visible light irradiation, releasing a trifluoromethyl radical 42. The radical then adds to the double bond of N-arylacrylamide, forming intermediate radical 43. Subsequently, this intermediate undergoes intramolecular
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Published 24 Jun 2025

Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

  • Betty A. Kustiana,
  • Galuh Widiyarti and
  • Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

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  • (2022) investigated the visible-light-mediated amidation of cinnamic acid (7) by using ethyl 2-diazoacetate and acetonitrile to give its corresponding amide 103 in excellent yield (Scheme 32) [29]. The reactive free carbene 104 was released upon light exposure of the diazo ester leading to the nitrilium
  • proceeding via C–N-bond cleavage of the oxidized tertiary amine 116 (Scheme 35) [70]. Cinnamic acid (7) was activated by forming the acyl radical 118 after −OPyf group cleavage from 117. Recently, Li and co-workers (2024) studied visible-light-mediated FeCl3-catalyzed reductive transamidation of nitro
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Published 28 May 2025

Biobased carbon dots as photoreductants – an investigation by using triarylsulfonium salts

  • Valentina Benazzi,
  • Arianna Bini,
  • Ilaria Bertuol,
  • Mariangela Novello,
  • Federica Baldi,
  • Matteo Hoch,
  • Alvise Perosa and
  • Stefano Protti

Beilstein J. Org. Chem. 2025, 21, 1024–1030, doi:10.3762/bjoc.21.84

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  • ); triarylsulfonium salts; visible light; Introduction Carbon dots (CDs) are a class of zero-dimensional carbon-based semiconducting nanoparticles bearing on the surface a wide range of functional groups, such as carboxylic acids, alcohols, and amines, that garnered significant attention in the last decade among the
  • biocompatibility. The electrochemical properties of such materials have been then evaluated by cyclic voltammetry (CV). For all the properties mentioned above, CDs emerged as low-cost and sustainable photocatalysts. Indeed, upon visible-light irradiation, the generated excited state CD* can operate as either
  • types of CDs and aims to promote the use of these sustainable materials, it opens the way for further exploitation of such compounds in visible-light-catalyzed reactions. UV–vis spectra of the CDs. All the measurements have been performed in water, except for CD-a-GLU, where a H2O/acetonitrile 1:1
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Published 26 May 2025

Study of tribenzo[b,d,f]azepine as donor in D–A photocatalysts

  • Katy Medrano-Uribe,
  • Jorge Humbrías-Martín and
  • Luca Dell’Amico

Beilstein J. Org. Chem. 2025, 21, 935–944, doi:10.3762/bjoc.21.76

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  • Supporting Information File 1, Table S3). As we expected, due to the blue-shifted absorption presented in molecules 4a and 6a, it was impossible to excite them under visible light (400 nm). Gratifyingly, PC 5a delivered product 8 with a promising 63% NMR yield. Next, we compare the photocatalytic behavior of
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Published 14 May 2025

Recent advances in controllable/divergent synthesis

  • Jilei Cao,
  • Leiyang Bai and
  • Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

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  • enantiocontrol. Conversely, the bulky tert-butyl-decorated (R)-spirophosphoramidite L5 imposed a confined cavity, steering selectivity toward Si–C(sp2)-bond activation and predominantly afforded the regioisomeric (S)-2-silacyclohexenylarenes 18. In 2025, Gong and co-workers reported a visible-light-mediated
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Published 07 May 2025

Substituent effects in N-acetylated phenylazopyrazole photoswitches

  • Radek Tovtik,
  • Dennis Marzin,
  • Pia Weigel,
  • Stefano Crespi and
  • Nadja A. Simeth

Beilstein J. Org. Chem. 2025, 21, 830–838, doi:10.3762/bjoc.21.66

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  • reported to either bathochromically shift the UV–vis absorption spectrum or lead to a better separation of the n→π* bands of the two photoisomers and allow for visible-light-responsive switches [23][24][25][26]. In recent years, heteroaryl azobenzene derivatives have revealed superior properties to
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Published 25 Apr 2025

Photocatalyzed elaboration of antibody-based bioconjugates

  • Marine Le Stum,
  • Eugénie Romero and
  • Gary A. Molander

Beilstein J. Org. Chem. 2025, 21, 616–629, doi:10.3762/bjoc.21.49

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  • ) that can form covalent bonds when exposed to UV or visible light. These photoaffinity tags or crosslinkers are designed to bind to specific biomolecules, such as proteins, nucleic acids, or lipids, in a highly selective manner. The light irradiation triggers a chemical reaction, such as a bond
  • the agency of low-energy visible light with specific functional groups on biomolecules. This allows precise control over the conjugation process, enabling targeted modifications without affecting non-reactive sites. Although previous reviews have discussed the more traditional synthetic methods
  • emerged as a transformative approach in the modification of proteins, enabling researchers to achieve selective and efficient conjugation under mild conditions [37]. By utilizing visible light and transition-metal catalysts, this technique allows the generation of reactive intermediates that can
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Published 18 Mar 2025

Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye

  • Metodej Dvoracek,
  • Brendan Twamley,
  • Mathias O. Senge and
  • Mikhail A. Filatov

Beilstein J. Org. Chem. 2025, 21, 500–509, doi:10.3762/bjoc.21.37

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  • E. M. Kosower in 1978. In this study, we report the topochemical cycloaddition of diethyl 2,6-dichloro-1,7-dioxo-1H,7H-pyrazolo[1,2-a]pyrazole-3,5-dicarboxylate (Cl2B), initiated by visible light. Crystal structure analysis confirmed that the reactive double bonds are parallel and coplanar, in line
  • with the Schmidt criteria for topochemical cycloaddition. Additionally, two other bimane derivatives with different substitution patterns were synthesized and investigated. Our findings suggest that functionalizing bimanes to redshift their absorption maxima into the visible-light spectrum provides a
  • a [2 + 2] cycloaddition reaction, with approximately 20% yield of the dimer in the crystal. This was particularly notable, given that the compound had spent minimal time in solution with limited exposure to visible light, and no exposure to ultraviolet light. To further explore this phenomenon, we
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Published 05 Mar 2025

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

  • Francesco Mele,
  • Ana M. Constantin,
  • Andrea Porcheddu,
  • Raimondo Maggi,
  • Giovanni Maestri,
  • Nicola Della Ca’ and
  • Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

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  • rearrangements. Most organic molecules are colorless and, in fact, do not absorb visible light: highly energetic UV irradiation is typically needed. A milder approach is offered by photocatalytic approaches. Here, a photocatalyst is added to the reaction mixture to convert light energy into chemical potential to
  • transform molecules. Intriguingly, photocatalysts typically absorb harmless visible light and can be chosen ad hoc to trigger the desired chemistry. Indeed, the photocatalyst–substrate interaction can occur via energy transfer [4][5][6][7][8], single-electron transfer [9][10][11][12], or hydrogen-atom
  • interface two technologies, the authors opted to use mechanoluminescent powders to generate photons directly inside the jar. In more detail, SrAl2O4:Eu2+/Dy3+ (SAOED) was used as a mechanoluminescent material to drive the visible-light-mediated Hofmann–Loffler–Freytag (HLF) reaction (Scheme 12A). Thus, when
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Published 03 Mar 2025

Red light excitation: illuminating photocatalysis in a new spectrum

  • Lucas Fortier,
  • Corentin Lefebvre and
  • Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

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  • own a large span of colors depending on the nature of the metal and the ligands but also on the various oxidation states these compounds can attain. This property results on the absorption of a visible-light photon complementary to the observed color and has been extensively exploited in photoredox
  • efficiency of photoredox-catalyzed reactions. Absorption in the red region opens up innovative opportunities for photochemical transformations. First, the employed photon has the lowest energy in the electromagnetic spectrum of visible light, which allows for safer laboratory conditions in terms of
  • suppress side reactions. The cross-dehydrogenative coupling reactions, under near-infrared irradiation, was found to proceed via an energy-transfer mechanism involving singlet oxygen generation rather than the typical electron-transfer pathway observed in the presented visible-light-mediated reactions in
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Published 07 Feb 2025

Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

  • Yujun Pang,
  • Jinglan Yan,
  • Nawaf Al-Maharik,
  • Qian Zhang,
  • Zeguo Fang and
  • Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

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  • , Palestine 10.3762/bjoc.21.15 Abstract An efficient and eco-friendly approach for synthesizing difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles was established via a visible-light-promoted radical cyclization reaction. This method employed the readily accessible and inexpensive
  • target products in good to excellent yields. Mechanistic studies revealed that the reaction proceeds via a radical pathway. Keywords: cyclization; difluoromethylation; hypervalent iodine; polycyclic imidazole; visible light; Introduction Organofluorine compounds continue to play important roles in
  • reaction of unactivated alkenes within benzimidazole molecules using CF2HSO2Na [18]. Subsequently, in 2024, Jin [19] and Yang [20] developed visible light-induced difluoromethylation strategies for unactivated alkenes within benzimidazoles using different CF2H sources (CF2HSO2Na and ([Ph3PCF2H]+Br
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Published 30 Jan 2025

Cu(OTf)2-catalyzed multicomponent reactions

  • Sara Colombo,
  • Camilla Loro,
  • Egle M. Beccalli,
  • Gianluigi Broggini and
  • Marta Papis

Beilstein J. Org. Chem. 2025, 21, 122–145, doi:10.3762/bjoc.21.7

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  • and sulfur dioxide afforded vinyl sulfones with excellent regio- and stereoselectivity (Scheme 9) [22]. The authors used DABCO(SO2)2 to generate sulfur dioxide, and visible light irradiation and the mandatory presence of a photocatalyst for this transformation suggested a radical mechanism. The
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Published 14 Jan 2025

Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning

  • Pablo Quijano Velasco,
  • Kedar Hippalgaonkar and
  • Balamurugan Ramalingam

Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3

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  • with feedback DOE facilitated the rapid identification of appropriate solvents. Notably, the use of DMSO, DMF, and pyridine led to an enhanced yield of the monoalkylated product. An experimental setup was developed for single-droplet studies of visible-light photoredox catalysis using an oscillatory
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Published 06 Jan 2025

Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

  • Yang Chen,
  • Jiao He,
  • Hang Lin,
  • Hai-Feng Wang,
  • Ping Hu,
  • Bi-Qin Wang,
  • Ke-Qing Zhao and
  • Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

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  • ] in combination with tunable absorption and emission of visible light. Polar nematic phase [23] and chiral columnar phase materials [24] based on polar fluorobenzene rings have also recently emerged as interesting new classes of fluorous materials, revealing their enormous potential in the high-tech
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Published 16 Dec 2024

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

  • Lucía Campos-Prieto,
  • Aitor García-Rey,
  • Eddy Sotelo and
  • Ana Mallo-Abreu

Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261

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  • other approaches such as visible light, microwaves, heterogeneous catalysis, and ultrasound [12][13][14][15]. Due to its versatility, one of the most prevalent of these MCRs is the Ugi reaction [16]. This reaction generally combines an isocyanide with an acid, an amine, and an aldehyde or ketone to
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Published 03 Dec 2024

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

  • Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

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  • to absorb significant amounts of visible light photons, which allows them to reach an excited state. The excited porphyrin molecule is likely to undergo energy transfer (ET; photosensitization) or single-electron transfer (SET; photoredox catalysis) to substrate molecules (Figure 13). In
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Published 27 Nov 2024

Extension of the π-system of monoaryl-substituted norbornadienes with acetylene bridges: influence on the photochemical conversion and storage of light energy

  • Robin Schulte,
  • Dustin Schade,
  • Thomas Paululat,
  • Till J. B. Zähringer,
  • Christoph Kerzig and
  • Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 3061–3068, doi:10.3762/bjoc.20.254

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  • at 1.60–1.63 ppm, 1.69–1.71 ppm, 1.82–1.85 ppm, 2.07–2.11 ppm, and 2.21–2.25 ppm. Thus, it is possible to convert this monosubstituted norbornadiene efficiently into the corresponding quadricyclane with visible light, and thus also by sunlight. Unfortunately, the derivatives 1h and 1j–l,n could not
  • amounts of unidentified by-products formed. Nevertheless, it was shown exemplarily that the photoisomerization can be performed under milder conditions and upon excitation with visible light in the presence of [Ru(phen)3](PF6)2 as a photosensitizer. Under these conditions, the derivatives 1i and 1l were
  • converted quantitatively into quadricyclanes by irradiation with green light. Thus, it was shown with the latter results that the photosensitization with suitable triplet sensitizers enables mild conversion of visible light in chemical energy in quantitative photoreactions of norbornadienes, even in cases
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Published 21 Nov 2024
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  • visible-light irradiation or heating, CD was moved back to the azobenzene moiety, and the entire process was reversible. This system was further developed in 2005 by introducing bipyridinium moieties to implement the selective transfer of the wheel via heating or light irradiation (Figure 5B) [57]. During
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Published 19 Nov 2024

Advances in radical peroxidation with hydroperoxides

  • Oleg V. Bityukov,
  • Pavel Yu. Serdyuchenko,
  • Andrey S. Kirillov,
  • Gennady I. Nikishin,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

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  • in Kwon’s review [34]. Cu-catalyzed oxygen atom transfer with TBHP were discussed in the review [35]. The review by Xiao considered visible light-driven C–C bond cleavage enabled with organic peroxides [36]. This comprehensive review summarizes all ever published studies on radical peroxidation with
  • photocatalytic system under visible light irradiation (443 nm) [56]. Peroxidation of β-ketoesters, cyanoacetic esters, and malonic esters 37 was performed using the TBAI/TBHP system (Scheme 15) [57]. The highest product yields in the TBAI-catalyzed peroxidation were achieved with malonic acid esters, in contrast
  • in situ-generated Cu(I) complexes was developed (Scheme 23) [43]. 2-Phenylbutane (64) was converted into peroxide 65 in a 70% yield with 4% ee. A visible light-induced direct decarboxylative peroxidation of carboxylic acids 66 with the formation of peroxides 67 under metal-free conditions using Mes
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Published 18 Nov 2024

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

  • Ritu Mamgain,
  • Kokila Sakthivel and
  • Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

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  • position of quinoline N-oxides and pyridine N-oxides, utilizing hypervalent iodine salts as the arylation reagents. The reaction was facilitated by visible light in conjunction with a photocatalyst. The absence of either the photocatalyst or light resulted in only trace amounts of the product, underscoring
  • mechanism by adding 2 equivalents of TEMPO to the reaction mixture. The absence of the desired product indicated the involvement of a radical pathway in the process. The proposed reaction mechanism begins with the activation of eosin Y by visible light from 5 W blue LEDs, transitioning it to its excited
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Published 13 Nov 2024

Interaction of a pyrene derivative with cationic [60]fullerene in phospholipid membranes and its effects on photodynamic actions

  • Hayato Takagi,
  • Çetin Çelik,
  • Ryosuke Fukuda,
  • Qi Guo,
  • Tomohiro Higashino,
  • Hiroshi Imahori,
  • Yoko Yamakoshi and
  • Tatsuya Murakami

Beilstein J. Org. Chem. 2024, 20, 2732–2738, doi:10.3762/bjoc.20.231

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  • Instutite for Liberal Arts and Sciences (ILAS), Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan 10.3762/bjoc.20.231 Abstract We have reported that upon visible light irradiation, ferrocene-porphyrin-[60]fullerene triad molecules yield long-lived charge-separated states, enabling the control of the plasma
  • from a difference in electric charge on the two sides of the plasma membrane (approximately 5 nm thickness), with a slight excess of the positive ions inside relative to the negative ions outside. Our ferrocene-porphyrin-C60 triad molecule exhibited long-lived charge-separated states under visible
  • light irradiation [7], with the C60 species becoming negatively charged while the ferrocene moiety became positively charged (Figure 1a). This charge-separated state can be used to initiate nanoscale electric fields, e.g., Vm. The design of the triad molecules may also help to keep their orientation
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Published 30 Oct 2024

Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light

  • Francesco Gambuti,
  • Jacopo Pizzorno,
  • Chiara Lambruschini,
  • Renata Riva and
  • Lisa Moni

Beilstein J. Org. Chem. 2024, 20, 2722–2731, doi:10.3762/bjoc.20.230

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  • indole alkaloids. Here, we develop a novel approach for the one-pot multistep synthesis of different spiro[indole-isoquinolines]. The protocol proposed involves the visible light mediated oxidation of N-aryl tertiary amines using bromochloroform with the generation of a reactive iminium species, which
  • reacts with an isocyanide and an electron-rich aniline in a three-component Ugi-type reaction to give an α-aminoamidine. This compound might undergo an additional visible light-mediated oxidation to furnish a second iminium intermediate, which acts as electrophile in an intramolecular electrophilic
  • : isocyanide; multicomponent reactions; one-pot reaction; oxidation; spiroindolenine; Ugi reaction; visible light; Introduction Diversity-oriented synthesis (DOS) is a successful approach to biologically active scaffolds directed to create an enormous exploratory space in pharmaceutical hit discovery [1][2
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Published 29 Oct 2024

Photoluminescence color-tuning with polymer-dispersed fluorescent films containing two fluorinated diphenylacetylene-type fluorophores

  • Kazuki Kobayashi,
  • Shigeyuki Yamada,
  • Motohiro Yasui and
  • Tsutomu Konno

Beilstein J. Org. Chem. 2024, 20, 2682–2690, doi:10.3762/bjoc.20.225

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  • especially indispensable for our affluent life, is more difficult than the development of the blue-, yellow-, and red-light-emitting molecules mentioned above [24][25][26]. Therefore, to achieve white luminescence covering the entire spectral range of the visible light region, two or more colors of
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Published 23 Oct 2024
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