Enhanced reactivity of Li⁺@C₆₀ toward thermal [2 + 2] cycloaddition by encapsulated Li⁺ Lewis acid

• Hiroshi Ueno,
• Yu Yamazaki,
• Hiroshi Okada,
• Fuminori Misaizu,
• Ken Kokubo and
• Hidehiro Sakurai

Beilstein J. Org. Chem. 2024, 20, 653–660, doi:10.3762/bjoc.20.58

• progress in synthetic procedures has contributed to diversifying their properties, enabling widespread and interdisciplinary applications in various research fields, such as biomedicine, photovoltaic devices, and materials chemistry. Meanwhile, lithium ion-endohedral fullerenes (Li+@C60) [8], the first

Mono or double Pd-catalyzed C–H bond functionalization for the annulative π-extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives

• Nahed Ketata,
• Linhao Liu,
• Ridha Ben Salem and
• Henri Doucet

Beilstein J. Org. Chem. 2024, 20, 427–435, doi:10.3762/bjoc.20.37

• ; palladium; Introduction Substituted polyaromatics such as fluoranthenes (Figure 1) are widely used in materials chemistry due to their physical properties, and the introduction of a suitable functional group on the appropriate positions of fluoranthenes either allows their photophysical properties to be

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

• Christina Schøttler,
• Kasper Lund-Rasmussen,
• Line Broløs,
• Philip Vinterberg,
• Ema Bazikova,
• Viktor B. R. Pedersen and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

• Tetrathiafulvalene (TTF, Figure 1) is a redox-active molecule that has been widely explored in materials chemistry and supramolecular chemistry [1][2][3][4][5][6][7][8]. TTF reversibly undergoes two sequential one-electron oxidations, generating first a radical cation (TTF+•) and subsequently a dication (TTF2

Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts

• Nils Clamor,
• Mattis Damrath,
• Thomas J. Kuczmera,
• Daniel Duvinage and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 12–16, doi:10.3762/bjoc.20.2

• fast and reliable access to these substrates, which are profound structural motifs with application in medicinal and materials chemistry. Examples for direct syntheses of N-acyl heteroaromatic compounds. Scope of amides. aIsolated yields, 200 µmol scale, all reactions carried out in p-xylene, with 1.00

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia 10.3762/bjoc.19.139 Abstract The pyridine-3,5-dicarbonitrile moiety has gained significant attention in the field of materials chemistry, particularly in the development of heavy-metal-free pure organic light-emitting diodes (OLEDs). Extensive

• pyridine-3,5-dicarbonitrile moiety attracted a great deal of attention in the last decade in the field of materials chemistry, precisely in the development of novel heavy-metal-free pure organic light-emitting diodes (OLEDs). Inexpensive and environmentally friendly emitters are vital for organic

Practical synthesis of isocoumarins via Rh(III)-catalyzed C–H activation/annulation cascade

• Qian-Ci Gao,
• Yi-Fei Li,
• Jun Xuan and
• Xiao-Qiang Hu

Beilstein J. Org. Chem. 2023, 19, 100–106, doi:10.3762/bjoc.19.10

• Qian-Ci Gao Yi-Fei Li Jun Xuan Xiao-Qiang Hu Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education & Hubei Key Laboratory of Catalysis and Materials Science, School of Chemistry and Materials Science, South-Central Minzu University, Wuhan 430074, People’s Republic of

B–N/B–H Transborylation: borane-catalysed nitrile hydroboration

• Filip Meger,
• Alexander C. W. Kwok,
• Franziska Gilch,
• Dominic R. Willcox,
• Alex J. Hendy,
• Kieran Nicholson,
• Andrew D. Bage,
• Thomas Langer,
• Thomas A. Hunt and
• Stephen P. Thomas

Beilstein J. Org. Chem. 2022, 18, 1332–1337, doi:10.3762/bjoc.18.138

• of a double B–N/B–H transborylation mechanism. Keywords: boron; catalysis; hydroboration; nitrile; transborylation; Introduction Primary amines are prevalent throughout organic synthesis, finding regular application in materials chemistry, pharmaceuticals, and agrochemicals (Scheme 1a) [1][2][3

• . advised investigations. a) Derivatives of primary amines in materials chemistry, pharmaceuticals, and agrochemicals; b) this work: borane-catalysed nitrile hydroboration. Substrate scope of borane-catalysed nitrile hydroboration with HBpin. Conditions: nitrile (0.50 mmol), HBpin (3.5 equiv), H3B·SMe2 (10

Electrochemical and spectroscopic properties of twisted dibenzo[g,p]chrysene derivatives

• Tomoya Imai,
• Ryuhei Akasaka,
• Naruhiro Yoshida,
• Toru Amaya and
• Tetsuo Iwasawa

Beilstein J. Org. Chem. 2022, 18, 963–971, doi:10.3762/bjoc.18.96

• Tomoya Imai Ryuhei Akasaka Naruhiro Yoshida Toru Amaya Tetsuo Iwasawa Department of Information and Basic Science, Graduate School of Science, Nagoya City University, 1, Yamanohata, Mizuho-cho, Mizuho-ku, Nagoya, Aichi 467-8501, Japan Department of Materials Chemistry, Ryukoku University, Seta

Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions

• José G. Hernández,
• Karen J. Ardila-Fierro,
• Dajana Barišić and
• Hervé Geneste

Beilstein J. Org. Chem. 2022, 18, 182–189, doi:10.3762/bjoc.18.20

• , Medellín, Colombia Division of Materials Chemistry, Ruđer Bošković Institute, Bijenička c. 54, 10000 Zagreb, Croatia AbbVie Deutschland GmbH & Co. KG, Neuroscience Research, D-67008 Ludwigshafen, Germany 10.3762/bjoc.18.20 Abstract In the search for versatile reagents compatible with mechanochemical

Recent advances in the application of isoindigo derivatives in materials chemistry

• Andrei V. Bogdanov and
• Vladimir F. Mironov

Beilstein J. Org. Chem. 2021, 17, 1533–1564, doi:10.3762/bjoc.17.111

A straightforward conversion of 1,4-quinones into polycyclic pyrazoles via [3 + 2]-cycloaddition with fluorinated nitrile imines

• Greta Utecht-Jarzyńska,
• Karolina Nagła,
• Grzegorz Mlostoń,
• Heinz Heimgartner,
• Marcin Palusiak and
• Marcin Jasiński

Beilstein J. Org. Chem. 2021, 17, 1509–1517, doi:10.3762/bjoc.17.108

• structural motifs present in naturally occurring compounds as well as synthetic drugs and other functionalized organic molecules of great practical importance, e.g., in materials chemistry (Figure 1) [1][2][3][4]. Selective functionalization of 1,4-quinones is a challenging task in current organic synthesis

• -deficient nitrile imines was studied computationally to rationalize the observed pathways [41]. Hence, it is worth mentioning that the fused pyrazoles, which are attractive compounds for diverse practical applications in medicinal and materials chemistry, are available not only by the aza-Nenitzescu

• importance for medicinal chemistry, agrochemistry, and materials chemistry [44][45]. Experimental General information If not stated otherwise, reactions were carried out under inert atmosphere (argon) in flame-dried flasks with addition of the reactants by using syringes; subsequent manipulations were

Manganese/bipyridine-catalyzed non-directed C(sp³)–H bromination using NBS and TMSN₃

• Kumar Sneh,
• Takeru Torigoe and
• Yoichiro Kuninobu

Beilstein J. Org. Chem. 2021, 17, 885–890, doi:10.3762/bjoc.17.74

• Kumar Sneh Takeru Torigoe Yoichiro Kuninobu Department of Molecular and Material Sciences, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan Institute for Materials Chemistry and Engineering, Kyushu University, 6-1

Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles

• Soumyaranjan Pati,
• Renata G. Almeida,
• Eufrânio N. da Silva Júnior and
• Irishi N. N. Namboothiri

Beilstein J. Org. Chem. 2021, 17, 762–770, doi:10.3762/bjoc.17.66

• synthesis of new functionalized 1,2,3-triazoles. Keywords: azoles; cycloaddition; enones; heterocycles; 1,2,3-triazoles; Introduction 1,2,3-Triazoles are significant non-natural heterocyclic scaffolds with extensive applications in biochemistry, agrochemistry and materials chemistry [1][2][3][4][5]. This

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

• : Here, we briefly summarize the importance of fluorine atoms in organic molecules in the context of medicinal chemistry, materials chemistry, analytical chemistry and in the mechanistic studies of synthetic reactions. The importance of fluorination reactions in organic synthesis is reviewed exhaustively

Et₃N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

• Dharmender Singh,
• Vipin Kumar and
• Virender Singh

Beilstein J. Org. Chem. 2020, 16, 1740–1753, doi:10.3762/bjoc.16.146

• ] which were attributed to the presence of an electrophilic as well as a nucleophilic functionality in this natural product [1]. Encouraged by the applications of β-carboline and benzothiophene motifs in medicinal and materials chemistry, it was envisaged to construct a β-carboline-based novel molecular

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

• Shirakawa, leading to their shared award of the 2000 Chemistry Nobel Prize for “the discovery and development of conductive polymers” [101]. For the following 60 years, and still to this day, organic electronics is a vibrant field of research within materials chemistry and physics as a potential source of

Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes

• Grzegorz Mlostoń,
• Mateusz Kowalczyk,
• André U. Augustin,
• Peter G. Jones and
• Daniel B. Werz

Beilstein J. Org. Chem. 2020, 16, 1288–1295, doi:10.3762/bjoc.16.109

• materials chemistry, and electrochemical studies [19]. In continuation of our studies on organic sulfur compounds and the mechanisms of their reactions, the main goal of the present work was the examination of the formal [3 + 2]-cycloaddition reactions of ferrocenyl-substituted thioketones 8 with D–A

Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations

• Md. Shafiqur Rahman and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2020, 16, 524–529, doi:10.3762/bjoc.16.48

• synthesis of π-extended phospholes. In this respect, our attention focused on the fusion of phosphole with triphenylene, which represents one of the most common disc-like PAH motifs in organic materials chemistry [19][20][21][22][23][24][25]. Herein, we report on the synthesis of triphenylene-fused

Synthesis of six-membered silacycles by borane-catalyzed double sila-Friedel–Crafts reaction

• Yafang Dong,
• Masahiko Sakai,
• Kazuto Fuji,
• Kohei Sekine and
• Yoichiro Kuninobu

Beilstein J. Org. Chem. 2020, 16, 409–414, doi:10.3762/bjoc.16.39

• Yafang Dong Masahiko Sakai Kazuto Fuji Kohei Sekine Yoichiro Kuninobu Interdisciplinary Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga-shi, Fukuoka 816-8580, Japan Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasugakoen, Kasuga-shi

Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

• Daniel R. Sutherland,
• Nidhi Sharma,
• Georgina M. Rosair,
• Ifor D. W. Samuel,
• Ai-Lan Lee and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2019, 15, 2914–2921, doi:10.3762/bjoc.15.285

• to the benzoquinone acceptor. Compound 3, where benzoquinone is para-conjugated to the diphenylamine donor group, exhibited thermally activated delayed fluorescence (TADF) with a biexponential lifetime characterized by a prompt ns component and a delayed component of 353 μs. Keywords: materials

• chemistry; physical organic chemistry; spectroscopy; thermally activated delayed fluorescence; Introduction Substituted benzoquinones and derivatives [1] have generated great interest, in particular due to their redox-active nature and their importance in biological mechanisms [2]. Compounds bearing

Aggregation-induced emission effect on turn-off fluorescent switching of a photochromic diarylethene

• Luna Kono,
• Yuma Nakagawa,
• Ayako Fujimoto,
• Ryo Nishimura,
• Yohei Hattori,
• Toshiki Mutai,
• Nobuhiro Yasuda,
• Kenichi Koizumi,
• Satoshi Yokojima,
• Shinichiro Nakamura and
• Kingo Uchida

Beilstein J. Org. Chem. 2019, 15, 2204–2212, doi:10.3762/bjoc.15.217

• Luna Kono Yuma Nakagawa Ayako Fujimoto Ryo Nishimura Yohei Hattori Toshiki Mutai Nobuhiro Yasuda Kenichi Koizumi Satoshi Yokojima Shinichiro Nakamura Kingo Uchida Department of Materials Chemistry, Ryukoku University, Seta, Otsu, Shiga 520-2194, Japan Department of Materials and Environmental

An overview of the cycloaddition chemistry of fulvenes and emerging applications

• Ellen Swan,
• Kirsten Platts and
• Anton Blencowe

Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209

• for the synthesis of complex polycyclic carbon scaffolds. As a result, fulvene cycloaddition chemistry has been employed extensively for the synthesis of natural products. More recently, fulvene cycloaddition chemistry has also found application to other areas including materials chemistry and dynamic

• combinatorial chemistry. This highlight article discusses the unusual properties of fulvenes and their varied cycloaddition chemistry, focussing on applications in organic and natural synthesis, dynamic combinatorial chemistry and materials chemistry, including dynamers, hydrogels and charge transfer complexes

• (and dynamic) under mild conditions at 25–50 °C (Scheme 18) [189]. At lower temperatures (−10 to 0 °C) the reaction was considerably slower, but overall suggests that certain fulvene DACs can be applied in DCC. Materials chemistry Despite their reactive nature, fulvenes have been successfully used in

Copper(I)-catalyzed tandem reaction: synthesis of 1,4-disubstituted 1,2,3-triazoles from alkyl diacyl peroxides, azidotrimethylsilane, and alkynes

• Muhammad Israr,
• Changqing Ye,
• Munira Taj Muhammad,
• Yajun Li and
• Hongli Bao

Beilstein J. Org. Chem. 2018, 14, 2916–2922, doi:10.3762/bjoc.14.270

• research and synthesis of functionalized compounds that have applications in medicinal chemistry, drug discovery, materials chemistry, and as well as in bioconjugates [2][3][4][5][6][7][8][9][10][11][12]. The copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction [13][14][15][16][17][18][19][20][21

Copolymerization of epoxides with cyclic anhydrides catalyzed by dinuclear cobalt complexes

• Yo Hiranoi and
• Koji Nakano

Beilstein J. Org. Chem. 2018, 14, 2779–2788, doi:10.3762/bjoc.14.255

• Yo Hiranoi Koji Nakano Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan 10.3762/bjoc.14.255 Abstract The alternating copolymerization of epoxides with cyclic anhydrides (CAs) is a highly diverse

Efficient catalytic alkyne metathesis with a fluoroalkoxy-supported ditungsten(III) complex

• Henrike Ehrhorn,
• Janin Schlösser,
• Dirk Bockfeld and
• Matthias Tamm

Beilstein J. Org. Chem. 2018, 14, 2425–2434, doi:10.3762/bjoc.14.220

• metallacyclobutadiene (MCBD) intermediates [12]. Ongoing progress in the development of highly active homogeneous alkyne metathesis catalysts (Figure 1) has increased the value of this method in natural product and materials chemistry. The contributions from our group to the development of alkyne metathesis catalysts