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Search for "photoredox" in Full Text gives 162 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction

  • Vyacheslav I. Supranovich,
  • Igor A. Dmitriev and
  • Alexander D. Dilman

Beilstein J. Org. Chem. 2020, 16, 3104–3108, doi:10.3762/bjoc.16.260

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  • (CF2CF2) has advanced considerably over the last decade [20], and the use of preformed tetrafluorinated building blocks [21] provides the most efficient way of making these molecules. Recently, we disclosed a photoredox method for the reductive radical fluoroalkylation of nitrones [22][23][24]. We have
  • annelation reaction for the synthesis of piperidines. Isolated yields are shown. a1.0 equiv of 2b was used. The proposed mechanism of the photoredox annelation reaction (asc = ascorbic acid). Optimization studies for the synthesis of 3a. Supporting Information Supporting Information File 506: Full
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Published 29 Dec 2020

Metal-free synthesis of biarenes via photoextrusion in di(tri)aryl phosphates

  • Hisham Qrareya,
  • Lorenzo Meazza,
  • Stefano Protti and
  • Maurizio Fagnoni

Beilstein J. Org. Chem. 2020, 16, 3008–3014, doi:10.3762/bjoc.16.250

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  • ], aryl sulfonates [36], and in aryl trifluoroethyl sulfate [37], Scheme 1a) followed by the reaction of the thus formed aryl cation with an aromatic substrate. In an alternative approach, aryl radicals may be generated under photoredox catalysis conditions (mostly from arene diazonium salts or aryl
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Published 08 Dec 2020

Controlled decomposition of SF6 by electrochemical reduction

  • Sébastien Bouvet,
  • Bruce Pégot,
  • Stéphane Sengmany,
  • Erwan Le Gall,
  • Eric Léonel,
  • Anne-Marie Goncalves and
  • Emmanuel Magnier

Beilstein J. Org. Chem. 2020, 16, 2948–2953, doi:10.3762/bjoc.16.244

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  • ]. The modern and green photoredox catalytic activation of SF6 was recently performed for the fluoro- and alkoxypentafluorosulfanylation of styrenes [21][22]. The same type of transformation was also described through the reductive activation of sulfur hexafluoride with TEMPO [23]. To the best of our
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Published 01 Dec 2020

Recent developments in enantioselective photocatalysis

  • Callum Prentice,
  • James Morrisson,
  • Andrew D. Smith and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

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  • transformative synthetic strategy, including in enantioselective synthesis. From the pioneering work by MacMillan [1] and Bach [2], enantioselective photocatalysis has grown into a well-established field of its own. A large proportion of photocatalysis focuses on photoredox catalysis, which involves single
  • with photoredox catalysis was reported by Nicewicz and MacMillan [1] for the alpha alkylation of aldehydes 1 with various alkyl bromides bearing an electron-withdrawing substituent 2, which while seemingly trivial, was not possible with enamine catalysis alone (Scheme 1). The proposed mechanism
  • photocatalysts used for this reaction, it is proposed the excited state of 9 is sufficiently reducing to initiate the chain mechanism through an oxidative quench. Moving away from electronically activated halides, MacMillan et al. investigated a tricatalytic system, utilising enamine, photoredox, and HAT
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Published 29 Sep 2020

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

  • Shahboz Yakubov and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

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  • . One exciting development in C–F bond formation is the use of small-molecule photosensitizers, allowing the reactions i) to proceed under mild conditions, ii) to be user-friendly, iii) to be cost-effective and iv) to be more amenable to scalability than typical photoredox-catalyzed methods. In this
  • reactions proceed under photoredox catalysis (PRC), involving Dexter electron transfer. Such photoredox reactions begin with the excitation of the photocatalyst (PC) by visible light, followed by a single-electron transfer (SET) between the excited photocatalyst and another molecule (quencher, Scheme 2A
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Published 03 Sep 2020

Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenes

  • Thomas Schneider,
  • Michael Keim,
  • Bianca Seitz and
  • Gerhard Maas

Beilstein J. Org. Chem. 2020, 16, 2064–2072, doi:10.3762/bjoc.16.173

Graphical Abstract
  • lithium acetylides [25]. By a photoredox-catalytic process, primary α-(trifluoromethyl)-α-(4-pyridyl)benzylamines were obtained from α-(trifluoromethyl)-benzaldoximes and 4-cyanopyridine [26]. We have recently introduced a new class of acetylenic iminium salts, namely 1-(trifluoromethyl)prop-2-yn-1
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Published 24 Aug 2020

A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates

  • Olusesan K. Koleoso,
  • Matthew Turner,
  • Felix Plasser and
  • Marc C. Kimber

Beilstein J. Org. Chem. 2020, 16, 1983–1990, doi:10.3762/bjoc.16.165

Graphical Abstract
  • radical addition, using photoredox catalysis, to allenamides and allencarbamates is reported. This transformation synthesizes N-acyl-N’-aryl-N,N’-allylaminals, and proceeds by a conjugated N-acyliminium intermediate that previously has principally been generated by electrophilic activation methods. The
  • radical adds to the central carbon of the allene giving a conjugated N-acyliminium that undergoes nucleophilic addition by arylamines and alcohols. Keywords: allenamide; allene; intermolecular; N-acyliminium; photoredox; Introduction Allenamides (Scheme 1, 1) and their congeners have attracted
  • subsequently formed radical (Scheme 3) [41]. The thought process behind this approach is based on three observations; (i) Akita and co-workers disclosure on the photoredox-catalyzed oxytrifluoromethylation of allenes 6 to give 2-trifluoromethylated allyl acetates 7 [42][43][44]; (ii) that intramolecular
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Published 12 Aug 2020

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

  • Lucas Guillemard and
  • Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

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  • previous functionalization, thus considerably reduce waste generation and a number of synthetic steps. In parallel, transformations involving photoredox catalysis promote radical reactions in the absence of radical initiators. They are conducted under particularly mild conditions while using the visible
  • catalytic system is extremely appealing. In that perspective, the scope of this review aims to present innovative reactions combining C–H activation and visible-light induced photocatalysis. Keywords: C–H activation; C–H functionalization; dual catalysis; photoredox catalysis; radical chemistry
  • )) [47]. Despite great advances achieved in the field of both, C–H activation and visible-light-induced photocatalysis, dual systems merging these two activation modes have remained underdeveloped until recently. In contrast, over the past decade, the design of new strategies combining photoredox
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Published 21 Jul 2020

Photoredox-catalyzed silyldifluoromethylation of silyl enol ethers

  • Vyacheslav I. Supranovich,
  • Vitalij V. Levin and
  • Alexander D. Dilman

Beilstein J. Org. Chem. 2020, 16, 1550–1553, doi:10.3762/bjoc.16.126

Graphical Abstract
  • -electron oxidation thereby supporting a photoredox cycle [22][23][24]. The silyl enol ether 2a derived from acetophenone was selected as a model substrate and the reaction with silane 1 (1.5 equiv) was evaluated (Scheme 2). The reactions were performed in dichloromethane, and reaction mixtures were
  • employed in photoredox reactions to scavenge acidic byproducts [28][29], could not be employed. Silane 1 is easily destroyed by bases (even by the amide group [30]) followed by the rapid addition of difluorocarbene to silyl enol ethers [19][20]. Disappointingly, we were unable to isolate ketone 3a using
  • borohydride, and the decreased reactivity of this ketone allowed its isolation. A proposed mechanism for the photoredox fluoroalkylation reaction is shown in Scheme 3. The photoexcited catalyst converts silane 1 into difluoromethylsilyl-based radical. The efficiency of [AuCl(μ-dppm)]2 compared to other
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Published 29 Jun 2020

Heterogeneous photocatalysis in flow chemical reactors

  • Christopher G. Thomson,
  • Ai-Lan Lee and
  • Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

Graphical Abstract
  • some interesting reactor designs that could be implemented to enhance organic synthesis. Keywords: air purification; flow chemistry; heterogeneous photoredox catalysis; organic synthesis; reactor design; water purification; Review 1 Introduction 1.1 Scope of the review This review aims to be of
  • discussion of the advantages and disadvantages to guide the reader in selecting the reactor best suited to their system. Following this, in Section 4, we review the recent applications of HPCats in flow reactors for synthetic organic chemistry through photoredox catalysis (PRC, Section 4.1) and energy
  • visible light through single-electron transfer processes, now referred to as visible light photoredox catalysis (PRC). A similar query on the Web of Science for the term “Photoredox” clearly shows the surge in PRC research following those reports, from 2010 onwards (Figure 1A). However, what is
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Published 26 Jun 2020

Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review

  • Alessandra Del Tito,
  • Havall Othman Abdulla,
  • Davide Ravelli,
  • Stefano Protti and
  • Maurizio Fagnoni

Beilstein J. Org. Chem. 2020, 16, 1476–1488, doi:10.3762/bjoc.16.123

Graphical Abstract
  • is a quite unexplored field, a notable exception being the seminal work published in 1984 by Cano-Yelo and Deronzier, where the authors reported one of the first applications of the Ru(bpy)32+ complex in photoredox catalysis (Scheme 1). This contribution described a photo-Pschorr cyclization
  • biaryls 5.1a–d in up to excellent yields at room temperature by using α-bromoesters as radical precursors and [fac-Ir(ppy)3] as the photoredox catalyst [49]. A similar photocatalyzed tandem insertion/cyclization approach based on isocyanides and amino acid/peptide-derived Katritzky salts as precursors of
  • - [55][56] phenanthridines was investigated. On the other hand, Umemoto’s reagent 7.2 was widely employed to introduce a trifluoromethyl group. In one instance, the visible-light irradiation of isocyanides 7.1 in the presence of excess 7.2 (4 equiv) and the Ru(bpy)32+ photoredox catalyst afforded the
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Published 25 Jun 2020

An overview on disulfide-catalyzed and -cocatalyzed photoreactions

  • Yeersen Patehebieke

Beilstein J. Org. Chem. 2020, 16, 1418–1435, doi:10.3762/bjoc.16.118

Graphical Abstract
  • . Under photoirradiation, organic disulfides can be easily cleaved into free thiyl radicals (RS•) and can reversibly add to unsaturated multiple bonds to catalyze a variety of functionalization reactions under mild conditions. In photoredox catalysis reactions, an excellent electron transfer ability and
  • variety of reactions, renders them a class of green, economic, mild, and chemoselective radical catalyst. Apart from this, they are also excellent HAT catalysts in photoredox catalysis systems [2][3]. In various types of organic photochemistry reactions, such as cyclizations, anti-Markovnikov additions
  • method is also applicable for the synthesis of a wide variety of cyclopentane derivatives [12]. In 2017, Huang and co-workers reported a [4 + 2] cycloaddition reaction promoted by blue LED light, using aromatic olefins as the precursor, an acridinium photoredox catalyst (Mes–Acr–Ph+BF4−), and disulfide
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Published 23 Jun 2020

Distinctive reactivity of N-benzylidene-[1,1'-biphenyl]-2-amines under photoredox conditions

  • Shrikant D. Tambe,
  • Kwan Hong Min,
  • Naeem Iqbal and
  • Eun Jin Cho

Beilstein J. Org. Chem. 2020, 16, 1335–1342, doi:10.3762/bjoc.16.114

Graphical Abstract
  • but also as electron donors in the photoredox cycle, and the results are reported herein. We began with the reaction of simple N-benzylideneaniline. However, this substrate did not furnish the desired products under several different photocatalysis conditions, including those reported by Rueping. We
  • partner and an electron donor in the photoredox cycle (Scheme 1c). It is likely that the presence of the additional phenyl group in the substrate stabilizes the α-amino radical intermediate and modulates its reactivity [46][47]. In addition to the cross-coupled 1,2-diamines, we envisioned the generation
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Published 18 Jun 2020

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow

  • Alexander V. Nyuchev,
  • Ting Wan,
  • Borja Cendón,
  • Carlo Sambiagio,
  • Job J. C. Struijs,
  • Michelle Ho,
  • Moisés Gulías,
  • Ying Wang and
  • Timothy Noël

Beilstein J. Org. Chem. 2020, 16, 1305–1312, doi:10.3762/bjoc.16.111

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  • residence time up to 16 times in comparison to the batch procedure, while achieving similar or higher yields. In addition, the use of inorganic bases was demonstrated to increase the reaction yield under batch conditions. Keywords: C–H functionalization; continuous-flow; organic synthesis; photoredox
  • , partially due to the general interest of the community into C–H functionalization methodologies [18][19], and partially thanks to the synthetic possibilities enabled by photoredox catalysis, a field widely explored in recent years [20][21][22]. In 2018, Ngai [23][24] and Togni [25] reported simple
  • photoredox protocols for the radical trifluoromethoxylation of unfunctionalized (hetero)arenes by using specifically designed CF3O radical-releasing agents (Scheme 1B). Following our long-standing interest in the development of continuous-flow approaches for C–H functionalization [18][26] and photochemical
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Published 15 Jun 2020

Oxime radicals: generation, properties and application in organic synthesis

  • Igor B. Krylov,
  • Stanislav A. Paveliev,
  • Alexander S. Budnikov and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107

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Published 05 Jun 2020

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

  • Stephanie G. E. Amos,
  • Marion Garreau,
  • Luca Buzzetti and
  • Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

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  • Stephanie G. E. Amos Marion Garreau Luca Buzzetti Jerome Waser Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL, SB ISIC LCSO, BCH 4306 1015 Lausanne, Switzerland 10.3762/bjoc.16.103 Abstract Organic dyes have emerged as a reliable class of photoredox
  • -, nitrogen-, oxygen-, and sulfur-centered radicals, open-shell charged species, and sensitized organic compounds. Keywords: organic dyes; photocatalysis; photoredox catalysis; radicals; reactive intermediates; Review Introduction In the last decade, synthetic organic chemistry has experienced the
  • each of these steps, the role of A or D is assumed by a redox-active agent, either the substrate, a sacrificial electron donor/acceptor, or a reactive intermediate. This approach, usually named photoredox catalysis, has known a remarkable growth in the last decade and has given access to both neutral
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Published 29 May 2020

Accelerating fragment-based library generation by coupling high-performance photoreactors with benchtop analysis

  • Quentin Lefebvre,
  • Christophe Salomé and
  • Thomas C. Fessard

Beilstein J. Org. Chem. 2020, 16, 982–988, doi:10.3762/bjoc.16.87

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  • Quentin Lefebvre Christophe Salome Thomas C. Fessard SpiroChem AG, Rosental area, WRO-1047-3, Mattenstrasse 24, 4058 Basel, Switzerland 10.3762/bjoc.16.87 Abstract Herein we report a workflow coupling photoredox-nickel dual-catalyzed N-arylation reactions to benchtop analysis for the efficient
  • thus be rapidly accessed, identifying privileged or challenging scaffolds and paving the way for further exploration. Keywords: benchtop analytics; fragment-based library; heterocyclic sp2–sp3 fragments; N-arylation; photoredox-nickel dual catalysis; Introduction Heterocyclic sp2–sp3 fragments are
  • initiated a high-throughput program of fragment-based library generation and after shortcomings using more classical cross-coupling conditions, we turned our attention to the photoredox-nickel dual-catalysis strategy recently reported by MacMillan and Buchwald [10]. The reported conditions use lower
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Published 12 May 2020

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

  • Rodrigo Costa e Silva,
  • Luely Oliveira da Silva,
  • Aloisio de Andrade Bartolomeu,
  • Timothy John Brocksom and
  • Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

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  • renewal of porphyrin applications in photocatalysis. Finally, the reaction scale in which the methodologies were developed are highlighted since this is an important parameter in the authors’ opinion. Keywords: energy transfer; photocatalysis; photooxygenation; photoredox; porphyrins; Introduction In
  • photoredox and energy transfer photocatalyzed reactions. The idea of this review is also to cover representative chemical transformations and recent applications in both batch and continuous-flow conditions, and emphasizing as much as possible, the scale in which the reactions were described. It is important
  • to clarify that other relevant reviews reporting applications of porphyrins in different perspectives can be found in the literature [19][20][21]. In addition, we emphasize that this review is organized into two topics. The first topic highlights the reactions that employ porphyrins as photoredox
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Published 06 May 2020

Aldehydes as powerful initiators for photochemical transformations

  • Maria A. Theodoropoulou,
  • Nikolaos F. Nikitas and
  • Christoforos G. Kokotos

Beilstein J. Org. Chem. 2020, 16, 833–857, doi:10.3762/bjoc.16.76

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  • presented. Keywords: aldehyde; green chemistry; photochemistry; photoinitiation; sustainable chemistry; Introduction Photochemistry, and especially photoredox catalysis have altered the way that modern researchers treat radical species [1][2][3][4]. In most cases, a metal-based photocatalyst is employed
  • , having multiple advantages since ligand manipulation can lead to optimized photoredox properties. Unfortunately, the use of metals can pose some critical disadvantages in an organic process. Especially since the natural abundance of various noble metals that are used as photocatalysts is limited and
  • supported the energy transfer pathway. Thus, the proposed triplet sensitization mechanism of the photocatalytic ATRA reaction is depicted in Scheme 25. In 2016, Ji and co-workers developed a new photoredox cross-dehydrogenative coupling (CDC) method for the α-heteroarylation of amides (α to nitrogen, e.g
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Published 23 Apr 2020

Photocatalytic deaminative benzylation and alkylation of tetrahydroisoquinolines with N-alkylpyrydinium salts

  • David Schönbauer,
  • Carlo Sambiagio,
  • Timothy Noël and
  • Michael Schnürch

Beilstein J. Org. Chem. 2020, 16, 809–817, doi:10.3762/bjoc.16.74

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  • Dolech 2, 5612 AZ Eindhoven, The Netherlands 10.3762/bjoc.16.74 Abstract A ruthenium-catalyzed photoredox coupling of substituted N-aryltetrahydroisoquinolines (THIQs) and different bench-stable pyridinium salts was successfully developed to give fast access to 1-benzyl-THIQs. Furthermore, secondary
  • (sp3) coupling; deaminative coupling; Katritzky salt; photoredox catalysis; Introduction The selective formation of new carbon–carbon bonds via direct C–H functionalization bears the potential of being a process of high efficiency [1][2][3]. Since C–H bonds are omnipresent in organic compounds it is
  • ], alkynation [17][18], or allylation [19]), this method has certain drawbacks, most importantly the frequent requirement of superstoichiometric amounts of an oxidant. Hence, alternative methods were investigated and photoredox catalysis proved to be a viable option [20][21][22]. By now, several different
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Published 21 Apr 2020

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

  • Bernd Strehmel,
  • Christian Schmitz,
  • Ceren Kütahya,
  • Yulian Pang,
  • Anke Drewitz and
  • Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

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  • metal ions. In this process, basically, in the presence of photoactive materials (PAs) such as photoinitiators, photosensitizers or photoredox catalysts, the photoexcitation of a photoredox system results in formation of reactive radicals. Those reactive radicals add monomer and the polymerization
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Published 18 Mar 2020

Visible-light-induced addition of carboxymethanide to styrene from monochloroacetic acid

  • Kaj M. van Vliet,
  • Nicole S. van Leeuwen,
  • Albert M. Brouwer and
  • Bas de Bruin

Beilstein J. Org. Chem. 2020, 16, 398–408, doi:10.3762/bjoc.16.38

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  • traditional reactivity of this compound. Here, we investigated the possibility of applying monochloroacetic acid as a substrate for photoredox catalysis with styrene to directly produce γ-phenyl-γ-butyrolactone. Instead of using nucleophilic substitution, we cleaved the carbon chlorine bond by single-electron
  • form in case of fac-[Ir(ppy)3]), which was proven by mass spectrometry and EPR spectroscopy for one of the catalysts (N,N-5,10-di(2-naphthalene)-5,10-dihydrophenazine) used in this work. The generation of HCl resulting from lactone formation could be an additional problem for organometallic photoredox
  • catalysts used in this reaction. In an attempt to trap one of the radical intermediates with TEMPO, we observed a compound indicating the generation of a chloromethyl radical. Keywords: ATRA; catalysis; chloroacetic acid; lactone; photoredox; Introduction Monochloroacetic acid is an industrially important
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Published 16 Mar 2020

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

  • Rafia Siddiqui and
  • Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

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  • compounds, including bioactive natural and nonnatural products, but also due to its impact on the discovery of pharmaceutical candidates and the total synthesis of intricate natural products. On the other hand, more recently, the field of photoredox catalysis has become an indispensable and unparalleled
  • highly desirable to the scientific community. In this review, we mainly highlight the impact on, and the utility of, photoredox catalysts in inert ortho and para C–H bond functionalizations. Although a surge of research papers, including reviews, demonstrating C–H functionalizations have been published
  • in this vital area of research, to our best knowledge, this is the first review that focuses on ortho and para C–H functionalizations by photoredox catalysis to provide atom- and step-economic organic transformations. We are certain that this review will act as a promoter to highlight the application
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Published 26 Feb 2020

Synthesis of acremines A, B and F and studies on the bisacremines

  • Nils Winter and
  • Dirk Trauner

Beilstein J. Org. Chem. 2019, 15, 2271–2276, doi:10.3762/bjoc.15.219

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  • undergo Diels–Alder reactions with electron-rich dienophiles [13][14][15][16][17], treatment of 5 with Fukuzumi’s catalyst [18] under illumination with blue light only led to decomposition of the starting material (Table 1, entry 15). Notably, a photoredox catalyst with a lower oxidation potential could
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Published 23 Sep 2019

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

  • Xiaowei Li,
  • Xiaolin Shi,
  • Xiangqian Li and
  • Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

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  • co-workers [117] explored a simple and facile method to access δ-trifluoromethylated carboxamides and sulfonamides through a copper-catalyzed 1,5-hydrogen atom transfer (Scheme 58). Other catalysts: In 2013, Gouverneur and co-workers [118] described a photoredox-based catalytic approach to afford
  • oxidative decarboxylation. Then, Cu(CF3)2 provides a CF3 group to alkyl radicals to obtain the final product. Very recently, MacMillan et al. [120] discovered an efficient approach to the decarboxylative trifluoromethylation of aliphatic carboxylic acids via the combination of photoredox and copper
  • catalysis (Scheme 61). The method tolerates a myriad of primary, secondary and tertiary carboxylic acids and provides the corresponding CF3 analogue in good to excellent yields. Details of the proposed dual copper–photoredox cycle are shown in Scheme 61. The Ir(III) photocatalyst Ir[dF(CF3)ppy]2(4,4
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Published 23 Sep 2019
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