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Search for "C–C bond" in Full Text gives 463 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Formaldehyde surrogates in multicomponent reactions

  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

Graphical Abstract
  • reacts with the enolate of the ketone, which is stabilized by coordination with Fe(III), resulting in the formation of the CC bond. A further oxidative aromatization process affords compound I. Compared to the protocol developed by Zhang et al. [24], the reaction is less regioselective, as Troger’s base
  • " of the methyl sulfur group in intermediate 22 for the cleavage of the C–S bond. In the end, the CC bond is formed between intermediate 23 and the enol form from the methyl ketone 18. Sodium carbonate is added to prevent too much acidification of the reaction medium and to deprotonate the NH that
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Review
Published 13 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

Graphical Abstract
  • using an anti-solvent (H2O). To account for the unique outcome of photomechanochemical conditions, the authors performed a DFT study and introduced the concept of mechanosusceptibility. Briefly, they computationally applied a force along the CC-bond-forming tensor that would result in the formation of
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Published 03 Mar 2025

Unraveling aromaticity: the dual worlds of pyrazole, pyrazoline, and 3D carborane

  • Zahra Noori,
  • Miquel Solà,
  • Clara Viñas,
  • Francesc Teixidor and
  • Jordi Poater

Beilstein J. Org. Chem. 2025, 21, 412–420, doi:10.3762/bjoc.21.29

Graphical Abstract
  • a π system with 6 π electrons [11]. When fused with a benzene ring, sharing a CC bond, it remains aromatic, which is the case of indazole. Pyrazoline (C3H6N2), similar to pyrazole, formally has only one double bond and a lone pair on the nitrogen, so it does not satisfy Hückel's rule and it is
  • therefore non-aromatic. Even when fused with benzene via a CC bond, pyrazoline remains non-aromatic, which is the case of indazoline. Icosahedral carboranes are globular molecular clusters made of carbon and boron, displaying 3D aromaticity [12][13][14][15]. Their unique properties – such as aromaticity
  • compared to the CC bond by 2.4 kcal/mol further supports the above statement [44]. Next, we have compared the above o-carborane-fused pyrazoles with a series of reference systems with the aim to better understand the electronic structure of the fused heterocycle and its aromaticity (Figure 3). First, the
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Published 21 Feb 2025

Molecular diversity of the reactions of MBH carbonates of isatins and various nucleophiles

  • Zi-Ying Xiao,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2025, 21, 286–295, doi:10.3762/bjoc.21.21

Graphical Abstract
  • Figure 1 and Figure 2, it can be found that the C=C bond is located in the unit of the pyrrolidine-2,5-dione, while the scaffold of indolin-2-one is connected via a C–C single bond with the unit of the pyrrolidine-2,5-dione. Therefore, an allyl rearrangement must proceed in the reaction process, which is
  • used in the reaction, a direct Michael addition of the arylamine to the C=C bond of the maleimide unit and sequential elimination of carbon dioxide and tert-butoxide ion gives the intermediate B, which in turn undergoes an allylic rearrangement to afford the product 5. In this process, no extra
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Published 06 Feb 2025

Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions

  • Dmitry E. Shybanov,
  • Maxim E. Kukushkin,
  • Eugene V. Babaev,
  • Nikolai V. Zyk and
  • Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18

Graphical Abstract
  • participation of the C=C bond. Apparently, the ratio of the adducts of the Diels–Alder (i.e., I) and the hetero-Diels–Alder reaction (i.e., II) was strongly influenced by steric factors; a decreased steric hindrance in the initial CH acid derivatives led to a more selective formation of the structures I. This
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Published 04 Feb 2025

Streamlined modular synthesis of saframycin substructure via copper-catalyzed three-component assembly and gold-promoted 6-endo cyclization

  • Asahi Kanno,
  • Ryo Tanifuji,
  • Satoshi Yoshida,
  • Sota Sato,
  • Saori Maki-Yonekura,
  • Kiyofumi Takaba,
  • Jungmin Kang,
  • Kensuke Tono,
  • Koji Yonekura and
  • Hiroki Oguri

Beilstein J. Org. Chem. 2025, 21, 226–233, doi:10.3762/bjoc.21.14

Graphical Abstract
  • reaction involves an in situ generation of the iminium cation A followed by isomerization to the thermodynamically more stable iminium cation B. Subsequent nucleophilic attack of a copper acetylide enabled regioselective CC bond formation at the C11 position. After removal of the cyclic acetal, the
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Published 28 Jan 2025

Recent advances in electrochemical copper catalysis for modern organic synthesis

  • Yemin Kim and
  • Won Jun Jang

Beilstein J. Org. Chem. 2025, 21, 155–178, doi:10.3762/bjoc.21.9

Graphical Abstract
  • has emerged as a potential synthetic tool for the formation of new C–C, and C–heteroatom bonds using electricity to replace the stoichiometric amounts of conventional chemical redox reagents [47]. CC Bond formation In 2019, the Ackermann group established a synthetic method for isoindolones using a
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Published 16 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

Graphical Abstract
  • presence of catalytic amounts of Cu(OTf)2 lead to the formation of the products through formation of one CC bond and three C–N bonds (Scheme 26) [44]. The same procedure allows a more general scope, giving access to imidazo[1,2-a]pyrimidine, imidazo[1,2-a]pyrazine and imidazo[2,1-b]thiazole derivatives
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Published 14 Jan 2025

Recent advances in organocatalytic atroposelective reactions

  • Henrich Szabados and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

Graphical Abstract
  • the final step of the reaction, ring opening by the CC bond cleavage yields the desired product 203. The first phosphoric acid C39-catalyzed asymmetric cycloaddition–elimination cascade reaction of 2-naphthol or phenol enamide derivatives 204 with azonaphthalenes 205 was done by Xu et al. in 2021
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Published 09 Jan 2025

Non-covalent organocatalyzed enantioselective cyclization reactions of α,β-unsaturated imines

  • Sergio Torres-Oya and
  • Mercedes Zurro

Beilstein J. Org. Chem. 2024, 20, 3221–3255, doi:10.3762/bjoc.20.268

Graphical Abstract
  • (Scheme 3). The reaction of 3-isothiocyanatooxindoles 4 and ketimines 7 led to the (3 + 2) cycloaddition through the C=C bond of the α,β-unsaturated imine instead of the C=N bond, affording various spirocyclic derivatives 8 with excellent yields (92–98%), diastereoselectivities (15:1–20:1 dr), and
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Published 10 Dec 2024

Tunable full-color dual-state (solution and solid) emission of push–pull molecules containing the 1-pyrindane moiety

  • Anastasia I. Ershova,
  • Sergey V. Fedoseev,
  • Konstantin V. Lipin,
  • Mikhail Yu. Ievlev,
  • Oleg E. Nasakin and
  • Oleg V. Ershov

Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251

Graphical Abstract
  • rigidity along the CC bond between the heterocycle and ethene bridge due to the fused cyclic fragment. As a consequence of the additional ring, the fluorescence efficiency increased. At the same time, solid-state emission was observed due to the steric hindrance, which prevented intermolecular
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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

Graphical Abstract
  • 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 CC bond cleavage enabled with organic peroxides [36]. This comprehensive review summarizes all ever published studies on radical peroxidation with
  • aid of the ortho-directing group to give the palladium intermediate B, which undergoes reductive elimination to establish the CC bond. A Cu-catalyzed difunctionalization of styrenes 211 with TBHP and N-hydroxyphthalimide (NHPI) (212) as sources of O-functional groups was reported (Scheme 66) [135
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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

Graphical Abstract
  • , CC bond formation was reported by Chen and colleagues in 2020 via the arylation of vinyl pinacol boronates 23 by using diaryliodonium salts 16 to yield trans-arylvinylboronates 24 in the absence of a metal catalyst [62]. The optimized reaction conditions involve the reaction of substituted
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Published 13 Nov 2024

C–C Coupling in sterically demanding porphyrin environments

  • Liam Cribbin,
  • Brendan Twamley,
  • Nicolae Buga,
  • John E. O’ Brien,
  • Raphael Bühler,
  • Roland A. Fischer and
  • Mathias O. Senge

Beilstein J. Org. Chem. 2024, 20, 2784–2798, doi:10.3762/bjoc.20.234

Graphical Abstract
  • , Germany 10.3762/bjoc.20.234 Abstract Unlike their planar counterparts, classic synthetic protocols for CC bond forming reactions on nonplanar porphyrins are underdeveloped. The development of CC bond forming reactions on nonplanar porphyrins is critical in advancing this field of study for more complex
  • further substitution directly on the meso- or a meso-phenyl ortho/meta/para positions of a porphyrin, is the introduction of CC bond forming chemistry. This is typically achieved using palladium and/or another transition-metal catalyst [20]. Sonagashira [21], Suzuki–Miyaura [22], Heck [23], Stille [24
  • ][25], Negishi [26], and Kumada [27] coupling reactions, as well as modern iridium and rhodium-based coupling techniques [28], are just some examples of the CC bond formations that have been implemented to achieve complex substitution patterns and functional arrangements on porphyrins. Of these named
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Published 04 Nov 2024

Computational design for enantioselective CO2 capture: asymmetric frustrated Lewis pairs in epoxide transformations

  • Maxime Ferrer,
  • Iñigo Iribarren,
  • Tim Renningholtz,
  • Ibon Alkorta and
  • Cristina Trujillo

Beilstein J. Org. Chem. 2024, 20, 2668–2681, doi:10.3762/bjoc.20.224

Graphical Abstract
  • distance between the CH3 group in the catalyst and the epoxy carbon atom (3.45 Å vs 3.75 Å in TS_S_S), a steric clash between the two methyl groups occurs (Figure 9). This results in an inversion of stereochemistry via rotation of the epoxy CC bond, leading to the formation of the (R) product. As two TSs
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Published 22 Oct 2024

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

  • Nian Li,
  • Ruzal Sitdikov,
  • Ajit Prabhakar Kale,
  • Joost Steverlynck,
  • Bo Li and
  • Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

Graphical Abstract
  • =C bond in the Co–alkene complex, forming an intermediate alkyl radical, which is further anodically oxidized to produce an intermediate alkyl cation. Another indole molecule undergoes electrophilic alkylation by this intermediate, forming an indolyl cation, which upon deprotonation yields the final
  • orbital during enolate formation, thus providing mild redox conditions. After anodic oxidation, a carbon-centered radical at the α-position is formed, which undergoes stereocontrolled CC-bond formation with the silyl ether, forming a trimethylsilyl (TMS)-ketyl radical. A second anodic one-electron
  • , employing a radical relay strategy to produce polyaryl-functionalized alkanes [46]. The authors proposed that the initial anodic oxidation of indole generates an indole cation radical intermediate, which is successively deprotonated to form an indolyl carbon-centered radical. This radical then adds to the C
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Published 09 Oct 2024

Synthesis and conformational analysis of pyran inter-halide analogues of ᴅ-talose

  • Olivier Lessard,
  • Mathilde Grosset-Magagne,
  • Paul A. Johnson and
  • Denis Giguère

Beilstein J. Org. Chem. 2024, 20, 2442–2454, doi:10.3762/bjoc.20.208

Graphical Abstract
  • carbohydrates [44][45]. The CC bond lengths within the pyran rings of halogenated analogues are between 1.50 and 1.54 Å, which is similar to native talose (18, 1.52–1.53 Å) (Table 1, entries 1–4). However, all specified bond lengths within the pyran rings are shorter for halogenated analogues compared to α-ᴅ
  • to the non-halogenated compound. The puckering amplitude for an ideal cyclohexane chair, with CC bond lengths of 1.54 Å, is 0.63 Å [50]. The azimuthal angle (θ) represents the distortion of the ring. For pyranose rings, an azimuthal angle of θ = 0° represents a perfect 4C1 chair, and an angle of θ
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Published 27 Sep 2024

Hydrogen-bond activation enables aziridination of unactivated olefins with simple iminoiodinanes

  • Phong Thai,
  • Lauv Patel,
  • Diyasha Manna and
  • David C. Powers

Beilstein J. Org. Chem. 2024, 20, 2305–2312, doi:10.3762/bjoc.20.197

Graphical Abstract
  • iminoiodinane reacts directly with the olefin to generate a short-lived alkyl-bound iodinane 7 or iodonium species 8 (Scheme 4f). Ligand coupling from 7 or extrusion of iodobenzene from 8 would furnish a carbocation intermediate 9 which could undergo CC bond rotation prior to ring closure to form the aziridine
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Published 11 Sep 2024

Synthesis and reactivity of the di(9-anthryl)methyl radical

  • Tomohiko Nishiuchi,
  • Kazuma Takahashi,
  • Yuta Makihara and
  • Takashi Kubo

Beilstein J. Org. Chem. 2024, 20, 2254–2260, doi:10.3762/bjoc.20.193

Graphical Abstract
  • unit allows for spin localization at the 10-position of anthracene through CC bond rotation, resulting in a tail-to-tail σ-dimer (Figure 1b). The σ-dimer exhibits an equilibrium state between the monomer radical and the σ-dimer in solution, and mechano-stimulus-induced CC bond fission in the solid
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Published 05 Sep 2024

Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation

  • Andrey R. Galeev,
  • Maksim V. Dmitriev,
  • Alexander S. Novikov and
  • Andrey N. Maslivets

Beilstein J. Org. Chem. 2024, 20, 2208–2216, doi:10.3762/bjoc.20.188

Graphical Abstract
  • mainly via metal-catalyzed C–N or CC bond formation. Despite recent advances in the area of remote C–H functionalization, this strategy still requires some pre-functionalization of the starting material or the use of directing groups [28][29][30][31][32]. An alternative strategy is based on aromatic
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Published 02 Sep 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

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Published 16 Aug 2024

1,2-Difluoroethylene (HFO-1132): synthesis and chemistry

  • Liubov V. Sokolenko,
  • Taras M. Sokolenko and
  • Yurii L. Yagupolskii

Beilstein J. Org. Chem. 2024, 20, 1955–1966, doi:10.3762/bjoc.20.171

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  • -difluoroethylene and the disappearance of vinyl protons resonances in the 1H NMR spectra [78]. Addition to the C=C bond Halogen addition: 1,2-Difluoroethylene was reported to react with chlorine [46][79] and bromine [51] under irradiation, yielding 1,2-difluoro-1,2-dihaloethanes in moderate to high yield (Scheme 9
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Published 12 Aug 2024

Benzylic C(sp3)–H fluorination

  • Alexander P. Atkins,
  • Alice C. Dean and
  • Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 1527–1547, doi:10.3762/bjoc.20.137

Graphical Abstract
  • predominately considered to be stable to isolation conditions, secondary and tertiary suffer from the elimination of HF, especially in the presence of silica gel or glass vessels. Therefore, benzyl fluorides have been derivatised, for example in C–O, C–N and CC bond-forming reactions [18][19][20], thereby also
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Published 10 Jul 2024

Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C–O bonds in organic transformations

  • Mithu Roy,
  • Bitan Sardar,
  • Itu Mallick and
  • Dipankar Srimani

Beilstein J. Org. Chem. 2024, 20, 1348–1375, doi:10.3762/bjoc.20.119

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  • [28] introduced the photoredox-catalyzed hydroacylation of styrene derivatives via deoxygenation of challenging aliphatic carboxylic acids (Scheme 1). The deoxygenation was promoted by phosphine reagents to form acyl radicals. The acyl radicals reacted with the C=C bond and formed the expected product
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Published 14 Jun 2024

Rhodium-catalyzed homo-coupling reaction of aryl Grignard reagents and its application for the synthesis of an integrin inhibitor

  • Kazuyuki Sato,
  • Satoki Teranishi,
  • Atsushi Sakaue,
  • Yukiko Karuo,
  • Atsushi Tarui,
  • Kentaro Kawai,
  • Hiroyuki Takeda,
  • Tatsuo Kinashi and
  • Masaaki Omote

Beilstein J. Org. Chem. 2024, 20, 1341–1347, doi:10.3762/bjoc.20.118

Graphical Abstract
  • halides, which involved a rhodium-bis(benzyl) complex (Scheme 2) [21]. Following these outcomes, as part of a research program aimed at a wide range of Rh-catalyzed CC bond-formation reactions, in this paper, we report a Rh-catalyzed Ullmann-type homo-coupling reaction of aryl Grignard reagents. Results
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Published 12 Jun 2024
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