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

• configuration comprising indium–tin oxide (ITO) as the bottom electrode, a few μm thick organic layer as the active medium, and aluminum as the top electrode. The entire deposition process was carried out under a vacuum exceeding 2 × 10−6 mbar to ensure the integrity and purity of the layers. In our TOF setup

Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals

• Alessandro L. Alves,
• Simone V. Bernardino,
• Carlos H. Stadtlober,
• Edivandro Girotto,
• Giliandro Farias,
• Rodney M. do Nascimento,
• Sergio F. Curcio,
• Thiago Cazati,
• Marta E. R. Dotto,
• Juliana Eccher,
• Leonardo N. Furini,
• Hugo Gallardo,
• Harald Bock and
• Ivan H. Bechtold

Beilstein J. Org. Chem. 2023, 19, 1755–1765, doi:10.3762/bjoc.19.128

• the analysis procedure. AFM measurements of the organic films were performed using a Nanosurf EasyScan2 apparatus in tapping mode with a scanning rate of 1.0 Hz covering 512 × 512 lines. Hole-only devices were fabricated using indium tin oxide (ITO) coated glass plates (sheet resistance of about 15 Ω

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices

• Suangsiri Arunlimsawat,
• Patteera Funchien,
• Pongsakorn Chasing,
• Atthapon Saenubol,
• Taweesak Sudyoadsuk and
• Vinich Promarak

Beilstein J. Org. Chem. 2023, 19, 1664–1676, doi:10.3762/bjoc.19.122

• increasing voltage (CELIV) or MIS-CELIV technique [59][60][61]. Electron- and hole-only MIS devices were fabricated with the structures of indium tin oxide (ITO)/magnesium fluoride (MgF2) (20 nm)/TPECNz (100 nm)/lithium fluoride (LiF) (1 nm)/aluminum (Al) (100 nm) and ITO/MgF2 (20 nm)/TPECNz (100 nm

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp³)–H to construct C–C bonds

• Hui Yu and
• Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

• involved in the activation of DDQ by coordinating the carbonyl oxygen atom which leads to an increase in the oxidation activity of DDQ. Subsequently, Li et al. improved the above method, using a mixture of indium and copper salts as a catalyst, NHPI (N-hydroxyphthalimide) as a co-catalyst to achieve the

• cross-coupling of ethers with enamides. Ni(II)-catalyzed CDC of indoles with 1,4-dioxane. Chemo- and regioselective ortho- or para-alkylation of pyridines. Asymmetric CDC of 3,6-dihydro-2H-pyrans with aldehydes. CDC of heterocyclic aromatics with ethers. Indium-catalyzed alkylation of DHPs with 1,3

Group 13 exchange and transborylation in catalysis

• Dominic R. Willcox and
• Stephen P. Thomas

Beilstein J. Org. Chem. 2023, 19, 325–348, doi:10.3762/bjoc.19.28

• ][32][33][34][35][36][37][38][39], gallium [36][40][41][42][43][44], and indium [36][45] reagents being used for the preparation of group 13 reagents. Group 13 exchange has recently been used to enable catalytic turnover in traditionally stoichiometric reactions, expanding the use of group 13 compounds

• characterised by X-ray crystallography, lending support to the mechanism proposed by Schneider [118]. Indium catalysis Examples of group 13 exchange are limited with indium, even stoichiometrically [36][45], however Kobayashi demonstrated the InI-catalysed addition of allylic and allenylboranes to ketals

• , acetals, aminals, and alkyl ethers (Scheme 26) [119][120][121]. The proposed mechanism was analogous to the GaI catalysis by Schneider, with an In‒O/B‒C exchange proposed to drive catalytic turnover. Nakazawa reported an iron–indium cooperative catalytic system for the hydroboration of nitriles with HBpin

Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin

• János Máté Orosz,
• Dóra Ujj,
• Petr Kasal,
• Gábor Benkovics and
• Erika Bálint

Beilstein J. Org. Chem. 2023, 19, 294–302, doi:10.3762/bjoc.19.25

• Reddy et al. [48] is worth mentioning, who used metallic indium and ammonium chloride for the reduction of N3-β-CD. Continuous flow synthesis of 6A-O-(p-toluenesulfonyl)-β-CD (2) According to the literature, most of the tosylations of CDs took place under heterogeneous conditions. However, small solid

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

• Merve Karaman,
• Abhishek Kumar Gupta,
• Subeesh Madayanad Suresh,
• Tomas Matulaitis,
• Lorenzo Mardegan,
• Daniel Tordera,
• Henk J. Bolink,
• Sen Wu,
• Stuart Warriner,
• Ifor D. Samuel and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

• -emitting electrochemical cells LEECs were fabricated using DiKTa-OBuIm and DiKTa-DPA-OBuIm as emitters. The device stack was the following: ITO/PEDOT:PSS/emitter/Al (where ITO is indium tin oxide; PEDOT:PSS is poly(3,4-ethylenedioxythiophene):poly(styrenesulfonate)). The PEDOT:PSS and the emitter layers

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

Effect of a twin-emitter design strategy on a previously reported thermally activated delayed fluorescence organic light-emitting diode

• Ettore Crovini,
• Zhen Zhang,
• Yu Kusakabe,
• Yongxia Ren,
• Yoshimasa Wada,
• Bilal A. Naqvi,
• Prakhar Sahay,
• Tomas Matulaitis,
• Stefan Diesing,
• Ifor D. W. Samuel,
• Wolfgang Brütting,
• Katsuaki Suzuki,
• Hironori Kaji,
• Stefan Bräse and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2021, 17, 2894–2905, doi:10.3762/bjoc.17.197

• ; for example, high triplet energy, good film-forming ability. OLED devices Finally, DICzTRZ and ICzTRZ-based OLEDs were fabricated using the following device structure: ITO (indium tin oxide) (50 nm)/PEDOT:PSS (poly(3,4-ethylenedioxythiophene) polystyrene sulfonate) (35 nm)/PVK (poly(9-vinylcarbazole

Recent advances in the syntheses of anthracene derivatives

• Giovanni S. Baviera and
• Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

• although they are classified in other categories that are also appropriate. Takai, Kuninobu, and their research group used an indium catalyst to synthesize polycyclic aromatic compounds via a reductive-dehydration intramolecular cycloaromatization [51], which is a Bradsher-type reaction. The authors

• -Proline-catalyzed [4 + 2] cycloaddition reaction of naphthoquinones and α,β-unsaturated aldehydes. Iridium-catalyzed [2 + 2 + 2] cycloaddition of a 1,2-bis(propiolyl)benzene derivative with alkynes. Synthesis of several anthraquinone derivatives by using InCl3 and molecular iodine. Indium-catalyzed

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

• composite with platinum nanoparticles stabilized with poly(acrylic acid) [113]. Such a catalytic system, obtained by layer-by-layer self-assembly with the addition of poly(diallyldimethylammonium chloride) on the indium tin oxide surface, provided hydrogen formation in photoelectrolytic cycles with a

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

• Joseane A. Mendes,
• Paulo R. R. Costa,
• Miguel Yus,
• Francisco Foubelo and
• Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

• steric hindrance [1][14][44][45] (Scheme 5). Other contributions to the nucleophilic addition reactions to N-tert-butanesulfinyl imines were made by Yus and co-workers employing organozincates [46][47][48][49] and indium [50]. After this brief about the synthesis of enantiomerically pure N-tert

• allylic bromides in the presence of zinc or indium metals is a well-known reaction [66][67]. It is possible to control and predict the stereochemistry of the addition to get the corresponding homoallylamine derivative with a high level of stereocontrol. The reaction of chiral imine 14 with an excess of

• , when the allylation was performed in the presence of indium metal, in a saturated aqueous solution of sodium bromide, a mixture of the bromoallylation and allylation products 25 and 26, respectively, were obtained [69]. The addition of the allyl unit to the imines proceeded with total facial

Prins cyclization-mediated stereoselective synthesis of tetrahydropyrans and dihydropyrans: an inspection of twenty years

• Asha Budakoti,
• Pradip Kumar Mondal,
• Prachi Verma and
• Jagadish Khamrai

Beilstein J. Org. Chem. 2021, 17, 932–963, doi:10.3762/bjoc.17.77

• of indium metal to produce homoallylic alcohol 156 (Scheme 37), which underwent a silyl-Prins cyclization to form polysubstituted exo-methylene THPs 157 [72]. Tandem allylation–silyl-Prins cyclization Tetrahydropyran can also be synthesized stereoselectively by sequential allylation to an aldehyde

Indium-mediated C-allylation of melibiose

• Christian Denner,
• Manuel Gintner,
• Hanspeter Kählig and
• Walther Schmid

Beilstein J. Org. Chem. 2019, 15, 2458–2464, doi:10.3762/bjoc.15.238

• Christian Denner Manuel Gintner Hanspeter Kahlig Walther Schmid Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090, Vienna, Austria 10.3762/bjoc.15.238 Abstract The indium-mediated allylation reaction has been applied to melibiose, a disaccharidic substrate. This

• the elongated unit at the reducing end of the disaccharide. Keywords: carbohydrates; C–C bond formation; indium-mediated allylation; melibiose; ozonolysis; Introduction The tin and indium-mediated allylation (IMA) proved to be useful synthetic tools for the chain elongation of unprotected

• reported for the first time a tin-mediated allylation of unprotected carbohydrates followed by ozonolysis allowing for easy accessibility of the corresponding elongated sugars [2]. In the same year, Chan and Li introduced indium for the allylation of aldehydes and furthermore demonstrated the applicability

A review of the total syntheses of triptolide

• Xiang Zhang,
• Zaozao Xiao and
• Hongtao Xu

Beilstein J. Org. Chem. 2019, 15, 1984–1995, doi:10.3762/bjoc.15.194

• and its relatives from commercially available acid 32 (Figure 2, route J and Scheme 8) [46]. This synthesis highlights the utilization of an indium(III)-catalyzed cationic polycyclization of 17 and a palladium-catalyzed carbonylation–in situ lactone formation to construct the key intermediate 94

• formal synthesis of triptolide and triptonide (Figure 2, route M) [48]. This synthesis highlights the use of Noyori’s ruthenium-catalyzed enantioselective transfer hydrogenation to introduce the chiral center; the indium(III)-catalyzed cationic polyene cyclization to construct the tricyclic A-, B- and C

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

• Gagandeep Kour Reen,
• Ashok Kumar and
• Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

Enantioselective Diels–Alder reaction of anthracene by chiral tritylium catalysis

• Qichao Zhang,
• Jian Lv and
• Sanzhong Luo

Beilstein J. Org. Chem. 2019, 15, 1304–1312, doi:10.3762/bjoc.15.129

• treated with the corresponding metal phosphate, which can be prepared in situ following our previously described procedure (Scheme 2b,c) [37][38]. UV analysis indicated that the indium salt 1a or gallium salt 1b (0.05 mM) could induce ca. 92% dissociation of trityl bromide (0.05 mM) to generate the trityl

Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams

• Edorta Martínez de Marigorta,
• Jesús M. de Los Santos,
• Ana M. Ochoa de Retana,
• Javier Vicario and
• Francisco Palacios

Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104

• and heteroaromatic amines 2 and trimethylsilyl enol ethers 39 are combined in a three-component Mannich/lactamization reaction in the presence of an indium catalyst to yield twenty four 3-difluoroalkylisoindolinone derivatives 40. The starting 2-formylbenzoic acid 33 has been also employed in Ugi-type

Synthesis of polydicyclopentadiene using the Cp₂TiCl₂/Et₂AlCl catalytic system and thin-layer oxidation of the polymer in air

• Zhargolma B. Bazarova,
• Ludmila S. Soroka,
• Alex A. Lyapkov,
• Мekhman S. Yusubov and
• Francis Verpoort

Beilstein J. Org. Chem. 2019, 15, 733–745, doi:10.3762/bjoc.15.69

• performed using a DSC 204 F1 Phoenix (NETZSCH) at a heating rate 10 °С/min with aluminum pans (the lid was manually drilled to ensure the access of argon). The DSC instrument was first calibrated with an indium standard. Measurements were carried out under an inert argon (or air) atmosphere at a flow rate

Thiol-free chemoenzymatic synthesis of β-ketosulfides

• Adrián A. Heredia,
• Martín G. López-Vidal,
• Marcela Kurina-Sanz,
• Fabricio R. Bisogno and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2019, 15, 378–387, doi:10.3762/bjoc.15.34

• thiols (Scheme 1) [17][18][19][20][21], other methodologies employing different sulfur sources such as disulfides or silylsulfides have been described, which most of them involves metals, e.g., indium [22], copper [23], mercury [24], or organocatalysts [25]. β-Ketosulfides, in addition, play an important

Synthesis of unnatural α-amino esters using ethyl nitroacetate and condensation or cycloaddition reactions

• Glwadys Gagnot,
• Vincent Hervin,
• Eloi P. Coutant,
• Sarah Desmons,
• Racha Baatallah,
• Victor Monnot and
• Yves L. Janin

Beilstein J. Org. Chem. 2018, 14, 2846–2852, doi:10.3762/bjoc.14.263

• -(trifluoromethyl)benzaldehyde (3j) and acetic anhydride using indium(III) chloride [15] as a Lewis acid catalyst [16] without any solvent at room temperature pointed out a complete conversion into acylal 7 overnight. A similar reaction using pivaloyl anhydride and either indium(III) chloride or tetrafluoroboric

• monitoring of the reaction between compounds 7 or 8 and ethyl nitroacetate (4) in the presence of a catalytic amount of indium(III) chloride pointed out the occurrence of tangibly more of the expected acrylate 2j, although along with many byproducts. Indeed, in a typical experiment, upon reduction of the

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

• Sambasivarao Kotha,
• Milind Meshram and
• Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

• %) was prepared via a SM coupling of the dibromo compound 112 with 4-formylphenylboronic acid (100). Treatment of dialdehyde 113 with allyl bromide (28) in the presence of indium powder furnished the RCM precursor 114. Under the influence of the G-II catalyst 2 RCM of diolefinic compound 114 was realized

Tetrathiafulvalene – a redox-switchable building block to control motion in mechanically interlocked molecules

• Hendrik V. Schröder and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2018, 14, 2163–2185, doi:10.3762/bjoc.14.190

• -decorated TTF-rotaxanes was achieved by Gao and co-workers [95]. They deposited a thin-film of bistable donor–acceptor rotaxanes on an indium tin oxide (ITO)-coated substrate. A clean electrochemical switching on the substrate was observed with current–voltage curves showing a clear memory effect. The

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

Cross-coupling of dissimilar ketone enolates via enolonium species to afford non-symmetrical 1,4-diketones

• Keshaba N. Parida,
• Gulab K. Pathe,
• Shimon Maksymenko and
• Alex M. Szpilman

Beilstein J. Org. Chem. 2018, 14, 992–997, doi:10.3762/bjoc.14.84

• . Recently, Loh reported the palladium-catalyzed coupling of an acid chloride with premade isolable indium homoenolates (In(CH2CHRC=OR')2), 1.2 equiv relative to the acid chloride) to give the corresponding 1,4-diketones [5]. Yet the direct coupling of two enolates is inarguably the shortest and most direct