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Search for "arenes" in Full Text gives 280 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

  • Fatemeh Doraghi,
  • Seyedeh Pegah Aledavoud,
  • Mehdi Ghanbarlou,
  • Bagher Larijani and
  • Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

Graphical Abstract
  • succeeded in synthesizing various diaryl(alkyl) sulfides 5 through the sulfenylation of unactivated arenes 4 with an electrophilic sulfur reagent in the presence of a palladium catalyst (Scheme 3) [45]. In the second phase, dibenzothiophene derivatives 6 were obtained via subsequent intramolecular arylation
  • substitution to provide C2,C3-disulfenylated product 66 (Scheme 28). In the same year, Sutherland and Dodds disclosed a protocol for the C–H bond thioarylation of electron-rich arenes 4 like anisoles, acetanilides, phenols, and N-heterocycles in the presence of Fe(III) Lewis acid and ionic liquid [BMIM]NTf2 as
  • 102 were obtained in moderate to excellent yields with good to excellent enantioselectivities (Scheme 42) [76]. It should be noted that the authors did not define the exact role of the organocatalyst in the reaction mechanism. Transition-metal-free C–H sulfenylation of electron-rich arenes 103 by N
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Published 27 Sep 2023

Cyclization of 1-aryl-4,4,4-trichlorobut-2-en-1-ones into 3-trichloromethylindan-1-ones in triflic acid

  • Vladislav A. Sokolov,
  • Andrei A. Golushko,
  • Irina A. Boyarskaya and
  • Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2023, 19, 1460–1470, doi:10.3762/bjoc.19.105

Graphical Abstract
  • conjugated enones afford O,C-diprotonated forms under superelectrophilic activation conditions. These dications can participate in electrophilic aromatic substitution reactions with arenes ([11] and references therein). Recently, we have shown that the reaction of (E)-5,5,5-trichloropent-3-en-2-one [Cl3CCH
  • =CHC(=O)Me] with arenes in Brønsted superacid TfOH (triflic acid, CF3SO3H) furnishes 3-methyl-1-trichloromethylindenes (Scheme 1a) [11]. Based on NMR analysis in TfOH and theoretical DFT calculations, it has been found that the reaction proceeds through an intermediate formation of the O-protonated
  • form of the starting compound [Cl3CCH=CHC(=OH+)Me]. The presence of two strong electron-withdrawing substituents, the trichloromethyl group (CCl3) and a protonated carbonyl (C(OH+)Me), at the carbon–carbon double bond makes this O-protonated species electrophilic enough to react with arenes (Scheme 1a
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Published 27 Sep 2023

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

  • Nosheen Beig,
  • Varsha Goyal and
  • Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

Graphical Abstract
  • carboxylation of acidic arenes and heteroarenes has been reported by Cazin, Nolan and co-workers [90]. In this context, it was found that a combination of [(IPr)CuOH] (3 mol %) with CsOH in THF afforded the best results (Scheme 68), whereas the SIPr, IMes, and SIMes-based NHC–Cu complexes were found to be less
  • alkenylate a variety of electron-rich as well as electron-deficient (hetero)arenes. Of the three imidazolylidene derived NHC–CuCl catalysts, the best results (up to 94% yield) were obtained with [(IiPr)CuCl]. The method has several key features, such as mild reaction conditions, tolerance of various
  • )–H Arylation In 2014, Cazin and co-workers accomplished the C(sp2)–H arylation of acidic arenes by using a cooperative NHC–Cu/NHC–Pd catalytic system in the presence CsOH (Scheme 73) [95]. [(It-Bu)CuCl] changes in situ into the catalytically active species [(It-Bu)CuOH], which induces C(sp2)–H
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Published 20 Sep 2023

Exploring the role of halogen bonding in iodonium ylides: insights into unexpected reactivity and reaction control

  • Carlee A. Montgomery and
  • Graham K. Murphy

Beilstein J. Org. Chem. 2023, 19, 1171–1190, doi:10.3762/bjoc.19.86

Graphical Abstract
  • elimination (e.g., with the β-dicarbonyl or arene) could occur (see Scheme 1). A prominent example of the coupling occurring between the Lewis base and the arene is in reactions with fluoride, which has been translated to enable the radiofluorination of non-activated arenes. While this fluorination reaction
  • and electron-poor arenes 57, including hindered ortho-substituted derivatives (Scheme 12). Further derivatization of the spirocyclic motif led to SPIAd-derived iodonium ylides 58, whose radiofluorinations showed improved radiochemical conversions with a variety of arene derivatives (Scheme 13) [16
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Published 07 Aug 2023

Photoredox catalysis harvesting multiple photon or electrochemical energies

  • Mattia Lepori,
  • Simon Schmid and
  • Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

Graphical Abstract
  • photon (400–700 nm; 1.8–3.1 eV). In addition, this energy is also diminished by as much as ≈25% through vibrational relaxation, internal conversion and intersystem crossing [11] and hence, many highly stabilized molecules including important feedstock molecules such as arenes, haloarenes or olefins
  • limited to electron-poor arenes like diazonium/iodonium salts or aryl iodides with electron-withdrawing substituents as aryl radical precursors, due to the limited accessible reducing power of photocatalysts that relied on a monophotonic excitation event. However, the vast majority of inexpensive
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Published 28 Jul 2023

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

  • Xiu-Yu Chen,
  • Hui Zheng,
  • Ying Han,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73

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  • ]. The well-known Huisgen 1,4-dipoles have a special kind of zwitterionic intermediates and are usually prepared by a nucleophilic addition of pyridine, quinoline, isoquinoline and other aza-arenes to electron-deficient alkynes [4][5][6][7][8]. The reactive Huisgen 1,4-dipoles have been widely employed
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Published 29 Jun 2023

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

  • Nan Yang,
  • Yi-Yan Zhu,
  • Wei-Xiu Lin,
  • Yi-Long Lu and
  • Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

Graphical Abstract
  • supramolecular systems derived from water-soluble macrocycles, including cyclodextrins (CDs), calix[n]arenes (CXs), cucurbiturils (CBs), and pillararenes have been widely studied [2][6][7][8]. Similar to those macrocyclic acceptors, tribenzotriquinacene (TBTQ) derivatives, a class of versatile host molecules
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Published 08 May 2023

Transition-metal-catalyzed domino reactions of strained bicyclic alkenes

  • Austin Pounder,
  • Eric Neufeld,
  • Peter Myler and
  • William Tam

Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38

Graphical Abstract
  • proceeds similarly to Nakamura’s Fe-catalyzed methodology (Scheme 13) [48]. In 2017, the Cheng laboratory investigated the Co-catalyzed ring-opening/dehydration of oxabicyclic alkenes via the C–H activation of arenes (Scheme 15) [50]. First, the group explored the ortho-naphthylation of N-pyrimidinylindole
  • -catalyzed [3 + 2] annulation/ring-opening/dehydration domino reaction of oxabicyclic alkenes 30 with 2-(1-methylhydrazinyl)pyridine (MHP) directed arenes 87 for the synthesis of benzo[b]fluorenones 88 (Scheme 16) [52]. C–H bond functionalization with heterobicyclic alkenes as annulation partners has
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Published 24 Apr 2023

Transition-metal-catalyzed C–H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview

  • Louis Monsigny,
  • Floriane Doche and
  • Tatiana Besset

Beilstein J. Org. Chem. 2023, 19, 448–473, doi:10.3762/bjoc.19.35

Graphical Abstract
  • year, the group of Huang reported an elegant and straightforward palladium(II)-catalyzed ortho-selective trifluoromethylthiolation of arenes bearing various directing groups using the nucleophilic trifluoromethylthiolating source AgSCF3 in combination with Selectfluor® as oxidant (Scheme 6, 29 examples
  • groups as well as halogens (16b–f, 62–91% yields). The meta-substituted (16f) and disubstituted (16j) products were obtained in high yields (73% and 79%, respectively). In 2018, Anbarasan and co-workers described a palladium-catalyzed trifluoromethylthiolation of arenes by C–H bond activation bearing
  • moderate yields. Finally, the SeCF3-containing β-methylacrylamide 40n was also obtained in 37% yield. II. Transition-metal-catalyzed fluoroalkoxylation of (hetero)arenes by C–H bond activation II.1) Fluoroalkoxylation of aromatic C(sp2)–H bonds by transition-metal catalysis Over the last years, key
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Published 17 Apr 2023

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

Graphical Abstract
  • of 1,2-difunctionalized arenes with alkynes or carbon monoxide (Scheme 1b, III) [13][14][15][16], have been widely applied for the assembly of isocoumarins over the past decades. Recently, the transition-metal-catalyzed ortho C–H activation/annulation of benzoic acids has emerged as an attractive
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Published 30 Jan 2023

Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation

  • Julian Spils,
  • Thomas Wirth and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2023, 19, 27–32, doi:10.3762/bjoc.19.2

Graphical Abstract
  • nucleophilic arenes under oxidative acidic conditions.The synthesis of CDIS is more challenging since the arene moiety must be covalently connected to the iodoarene prior to cyclization. Recently, we published two new methods that describe the generation of carbon- and heteroatom-bridged CDIS [28][29]. Herein
  • isolated in 34% yield indicating that steric effects play a role during the oxidation step. We further wanted to investigate different arenes, but due to the lack of selectivity of the primary benzyl acetates in the Friedel–Crafts step, we were limited to para-substituted arenes, which unfortunately all
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Published 03 Jan 2023

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

  • Konstantin Lebedinskiy,
  • Volodymyr Lobaz and
  • Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

Graphical Abstract
  • . Tetracene has limited solubility in several organic solvents such as chloroform, DMSO, THF, and chlorinated arenes [34][35][36]. Its solubility sufficiently increases with temperature, even more in a sealed vial where low boiling point solvents can be heated more. This way, we obtained concentrated hot
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Published 25 Nov 2022

One-pot synthesis of 2-arylated and 2-alkylated benzoxazoles and benzimidazoles based on triphenylbismuth dichloride-promoted desulfurization of thioamides

  • Arisu Koyanagi,
  • Yuki Murata,
  • Shiori Hayakawa,
  • Mio Matsumura and
  • Shuji Yasuike

Beilstein J. Org. Chem. 2022, 18, 1479–1487, doi:10.3762/bjoc.18.155

Graphical Abstract
  • cyclopropanes with arenes [29]. They have also been used in Pd-catalyzed cross-coupling reactions to react with hypervalent iodonium salts, organostananes, and vinyl epoxides [30][31][32]. Moreover, there are reports of them serving as oxidizing agents for alcohols [33]. Two papers have recently reported
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Published 18 Oct 2022

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

Graphical Abstract
  • , 93%, 1l, 74%) positions. An increased temperature of 80 °C was required for the efficient hydroboration for ortho-substituted aryl nitriles (1f, 1g, 1h), due to increased steric encumbrance close to the nitrile bond. The chloro-, bromo-, and iodo-substituted arenes provide a functional handle for
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Published 26 Sep 2022

Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

  • Oleg A. Levitskiy,
  • Olga I. Aglamazova,
  • Yuri K. Grishin and
  • Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2022, 18, 1166–1176, doi:10.3762/bjoc.18.121

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  • recently, two publications from the Werz group appeared concerning anodic activation of donor–acceptor cyclopropanes followed by their functionalization with arenes [43] or yielding oxy-ketones or 1,2-dioxanes [44]; the latter process was inspired by a previous report of Buriez [45]. The anodic
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Published 08 Sep 2022

Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold

  • Dmitry Dar’in,
  • Grigory Kantin,
  • Alexander Bunev and
  • Mikhail Krasavin

Beilstein J. Org. Chem. 2022, 18, 1070–1078, doi:10.3762/bjoc.18.109

Graphical Abstract
  • optimum conditions for the C-arylation of diazo substrates 10 (60 equiv ArH, 1.5 equiv TfOH, DCM, rt, 15 min), we proceeded to investigate the scope of this transformation for 4-diazo-3(2H)-isoquinolones 10a–s as well as various arenes (Scheme 3). In all cases, this (generally high-yielding
  • , less electron-rich arenes furnished higher amounts of the 3-isoquinolone 15 byproduct compared to their electron-rich counterparts (cf. 9o vs 9p). Likewise, electron-donating substituents in the 4-diazo-3(2H)-isoquinolone benzene ring increased the tendency of 3-isoquinolones 15 to form (cf. 9(15)f–h
  • ). Using more reactive (electron-rich) arenes results in lower diastereoselectivity and regiospecificity of the reaction (cf. 9q, 9v, and 9w). The structure and the initially anticipated trans-configuration of the products 9 was unequivocally confirmed by 1H and 13C NMR spectroscopy as well as, in the case
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Published 22 Aug 2022

Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate

  • Hisanori Senboku,
  • Mizuki Hayama and
  • Hidetoshi Matsuno

Beilstein J. Org. Chem. 2022, 18, 1040–1046, doi:10.3762/bjoc.18.105

Graphical Abstract
  • 1,3,5-trimethoxybenzene or indoles in DMA containing 0.1 M iPr2NHEtBF4 using an undivided cell equipped with a Pt plate cathode and a Pt wire anode (a quasi-divided cell) resulted in selective formation of N-acyliminium ions of DMA at the anode, which reacted with arenes to give the corresponding
  • synthesis [1][2][3][4]. For example, Friedel–Crafts-type amidomethylation [5][6][7][8][9][10][11][12][13][14][15] proceeds efficiently by the reaction of N-acyliminium ions with electron-rich arenes to give the corresponding amidomethylated products in good yields. Since amides are important intermediates
  • has also been applied to organic synthesis [17][18][19][20]. However, when electrochemical oxidation of amides/carbamates in the presence of nucleophiles, such as electron-rich arenes or silyl enol ethers, is carried out for Friedel–Crafts-type amidomethylation, electrochemical oxidation of electron
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Published 18 Aug 2022

Copper-catalyzed multicomponent reactions for the efficient synthesis of diverse spirotetrahydrocarbazoles

  • Shao-Cong Zhan,
  • Ren-Jie Fang,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 796–808, doi:10.3762/bjoc.18.80

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  • include Me (6a), OMe (6b, 6c), NMe2 (6d), NO2 (6e), and Cl (6f, 6g), could be well tolerated in this reaction. Importantly, the reaction is not sensitive to the electronic properties of the arenes, as the substrates bearing either electron-donating (6a–d), or electron-withdrawing (6e–g) groups on the aryl
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Published 07 Jul 2022

Synthesis of α-(perfluoroalkylsulfonyl)propiophenones: a new set of reagents for the light-mediated perfluoroalkylation of aromatics

  • Durbis J. Castillo-Pazos,
  • Juan D. Lasso and
  • Chao-Jun Li

Beilstein J. Org. Chem. 2022, 18, 788–795, doi:10.3762/bjoc.18.79

Graphical Abstract
  • radicals under light irradiation for the diversification of arenes. To verify the generation of perfluoroalkyl radicals from compounds 1, we conducted an experiment with perfluorohexyl analogue 1b and 1,1-diphenylethylene (7) as a radical trapping agent (Scheme 4). Gratifyingly we observed the formation of
  • ), both in less than 6 hours (Scheme 5). Unsubstituted arenes such as naphthalene were well tolerated in this methodology and produced 72% isolated yield of the perfluorohexylated product 11b. The radical addition to unsubstituted benzene was also found to be possible affording perfluorooctylated product
  • in yields of 64% and 20%, respectively. Arenes containing halogens were attempted; however, in accordance to previous reported literature, the compounds were found to decompose under the ultraviolet radiation necessary for the homolysis of the reagent [25]. Lastly, some heteroaromatic substrates such
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Published 04 Jul 2022

Mechanochemical halogenation of unsymmetrically substituted azobenzenes

  • Dajana Barišić,
  • Mario Pajić,
  • Ivan Halasz,
  • Darko Babić and
  • Manda Ćurić

Beilstein J. Org. Chem. 2022, 18, 680–687, doi:10.3762/bjoc.18.69

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  • ; N-halosuccinimide; palladium(II); Introduction Electrophilic aromatic substitution [1][2][3] and ligand-directed transition-metal-catalyzed reactions [4][5][6][7][8] are among the most widely used synthetic approaches for the preparation of halogenated arenes. They are important precursors in cross
  • ][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46], their application in the synthesis of halogenated arenes is still scarce. In 2015, Bolm and Hernandez reported the halogenation of 2-phenylpyridine in a ball mill using [Cp*RhCl2]2 in combination with AgSbF6 as catalyst and N
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Published 15 Jun 2022

Direct C–H amination reactions of arenes with N-hydroxyphthalimides catalyzed by cuprous bromide

  • Dongming Zhang,
  • Bin Lv,
  • Pan Gao,
  • Xiaodong Jia and
  • Yu Yuan

Beilstein J. Org. Chem. 2022, 18, 647–652, doi:10.3762/bjoc.18.65

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  • Dongming Zhang Bin Lv Pan Gao Xiaodong Jia Yu Yuan College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. of China 10.3762/bjoc.18.65 Abstract An efficient Cu-catalyzed strategy for the direct C–H amination of arenes in high yields using N-hydroxyphthalimide as
  • applied in amination reactions [17][18][19][20][21][22][23][24]. Especially, N-hydroxyphthalimide can react with arenes directly in the presence of palladium [25] or gold [26] (Scheme 1, reactions 1 and 2). Recently, we found that iron catalyzes the amination of arenes with N-hydroxyphthalimide under air
  • (reaction 3) [27]. Herein, we report a method for the construction of aromatic amines via the copper-catalyzed intermolecular radical amination of arenes with N-hydroxyphthalimide (NHPI) under air. Results and Discussion Initially, N-hydroxyphthalimide (NHPI, 2a) was reacted with benzene, catalyzed by CuBr
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Published 03 Jun 2022

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

  • Man-Ping Li,
  • Nan Yang and
  • Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

Graphical Abstract
  • , supramolecular chemotherapy has received considerable attention by utilizing a supramolecular strategy to decrease the cytotoxicity of anticancer drugs to normal cells while preserving their cytotoxicity against cancer cells [11]. Supramolecular systems derived from macrocycles [12][13], such as calix[n]arenes
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Published 12 May 2022

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

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Published 11 Apr 2022

Site-selective reactions mediated by molecular containers

  • Rui Wang and
  • Yang Yu

Beilstein J. Org. Chem. 2022, 18, 309–324, doi:10.3762/bjoc.18.35

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  • containers. The emphasis is on those reactions that give different product distributions on the potential reactive sites inside the containers than they do outside, free in solution. Specific cases include site-selective cycloaddition and addition of arenes, reduction of epoxides, α,β-unsaturated aldehydes
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Published 14 Mar 2022

Regioselectivity of the SEAr-based cyclizations and SEAr-terminated annulations of 3,5-unsubstituted, 4-substituted indoles

  • Jonali Das and
  • Sajal Kumar Das

Beilstein J. Org. Chem. 2022, 18, 293–302, doi:10.3762/bjoc.18.33

Graphical Abstract
  • summarizing recent relevant literature reports. Keywords: annulation; cyclization; fused indoles; regioselectivity; SEAr; Introduction Over the decades, countless cyclization and annulation reactions of substituted arenes/heteroarenes involving an electrophilic aromatic substitution (SEAr) reaction as the
  • or annulation of: (A) substituted arenes/heteroarenes and (B) 3,5-unsubstituted, 4-substituted indoles. Indole C3 regioselective intramolecular alkylation of indolyl allyl carbonates. Indole C3 regioselective Michael-type cyclization in the total synthesis of (−)-indolactam V. Synthesis of azepino
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Published 08 Mar 2022
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