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Search for "C–C-bond formation" in Full Text gives 143 result(s) in Beilstein Journal of Organic Chemistry.

Electrochemical formal homocoupling of sec-alcohols

  • Kosuke Yamamoto,
  • Kazuhisa Arita,
  • Masashi Shiota,
  • Masami Kuriyama and
  • Osamu Onomura

Beilstein J. Org. Chem. 2022, 18, 1062–1069, doi:10.3762/bjoc.18.108

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  • electrolysis; Introduction Carbon–carbon bond formation is one of the most fundamental and important reactions in synthetic organic chemistry. Reductive coupling of carbonyl compounds known as pinacol coupling would be a powerful method to construct vic-1,2-diol scaffolds through CC bond formation [1][2
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Letter
Published 22 Aug 2022

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

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

Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

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  • base to catalyze the CC bond formation via a Michael addition of active methylene groups [31]. Therefore, in the presence of TBAB, the bromide assisted with the deprotonation of the phenacylmalononitrile to give a carbanion intermediate A. Secondly, the nucleophilic addition of carbanion A to electron
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Published 08 Aug 2022

Synthetic strategies for the preparation of γ-phostams: 1,2-azaphospholidine 2-oxides and 1,2-azaphospholine 2-oxides

  • Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 889–915, doi:10.3762/bjoc.18.90

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  • an efficient method for the synthesis of 1,2-azaphospholidine 2-oxides via the CC bond formation. Our research group achieved the synthesis of 1-alkyl-3-benzoyl-2-ethoxy-1,3-dihydrobenzo[d][1,2]azaphosphole 2-oxide derivatives 106 from ethyl N-alkyl-N-aryl-1-diazo-2-oxo-2-phenylethylphosphonamidates
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Published 22 Jul 2022

Identification of the new prenyltransferase Ubi-297 from marine bacteria and elucidation of its substrate specificity

  • Jamshid Amiri Moghaddam,
  • Huijuan Guo,
  • Karsten Willing,
  • Thomas Wichard and
  • Christine Beemelmanns

Beilstein J. Org. Chem. 2022, 18, 722–731, doi:10.3762/bjoc.18.72

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  • preferences. While the microbial UbiA Ptase catalyzes the CC-bond formation between an isoprenyl chain and the meta-position of p-hydroxybenzoate (PHB) in the ubiquinone-Coenzyme Q10 biosynthesis (Figure 1), Ptases of type MenA perform the key step in the menaquinone biosynthesis by prenylating 1,4-dihydroxy
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Published 22 Jun 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

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  • 18 via a concerted protonation and CC bond formation. Weakened dispersive interactions caused by a substituent or heteroatom resulted in low yields and reduced regioselectivities. In 2020, Li and Van der Eycken and co-workers reported the synthesis of densely functionalized, polycyclic azepino[5,4,3
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Commentary
Published 08 Mar 2022

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

  • Surendran Amrutha,
  • Sankaran Radhika and
  • Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

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  • emphasis given to green strategies. This is the first review on iron- and cobalt-catalyzed Sonogashira coupling reactions which comprehends literature up to 2020. Keywords: CC bond formation; cobalt; green reaction; iron; nanoparticles; Sonogashira; Introduction The palladium-catalyzed cross-coupling
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Published 03 Mar 2022

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

  • Ruan Carlos B. Ribeiro,
  • Patricia G. Ferreira,
  • Amanda de A. Borges,
  • Luana da S. M. Forezi,
  • Fernando de Carvalho da Silva and
  • Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

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  • exhibiting solid-state fluorescence, although the fluorescence partially disappears in solution, and there is a large shift to red and blue [98][99]. Carbon–carbon bond formation The main steps in a synthesis usually involve CC bond formation, which is usually the main reaction step, or functional group
  • transformations. Organometallics are the most commonly used catalysts to promote CC bond formation. In addition, other so-called classical reactions are also widely used, such as Friedel–Crafts alkylation and acylation, Wittig and Horner–Emmons reactions, carbonyl addition/substitution, α-alkylation, aldol
  • bond from β-NQS. Method A: NaOH, EtOH/H2O, 40 °C, 2 h; Method B: t-BuOK, PEG-300, rt, 6–10 min. C=C bond formation from β-NQS and substituted acetonitriles. Funding Fellowships granted by CNPq (301873/2019-4 and 306011/2020-4), CAPES (Financial Code 001), and FAPERJ (E-26/203.191/2017, E-26/202.800
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Published 05 Jan 2022

Iron-catalyzed domino coupling reactions of π-systems

  • Austin Pounder and
  • William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

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  • reported a similar approach towards the assembly of 2,2-disubstituted indolines from N-sulfonylanilines and substituted styrene derivatives [93]. In 2014, the Jiao group investigated the carbosulfonation of alkenes 60 for the synthesis of oxindoles 90 through sequential C–S/CC-bond formation (Scheme 16
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Published 07 Dec 2021

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

  • Ilya A. P. Jourjine,
  • Lukas Zeisel,
  • Jürgen Krauß and
  • Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2668–2679, doi:10.3762/bjoc.17.181

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  • aldehyde (33%) being generated (Table 2, entry 11). Similar results were obtained when adding iodine to promote benzylic oxidation [56] (Table 2, entry 12). Finally, Pd(OAc)2 was added in hopes of improving the mediation of CC bond formation [38] (Table 2, entry 13). Interestingly, here the yield of
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Published 02 Nov 2021

Synthesis of phenanthridines via a novel photochemically-mediated cyclization and application to the synthesis of triphaeridine

  • Songeziwe Ntsimango,
  • Kennedy J. Ngwira,
  • Moira L. Bode and
  • Charles B. de Koning

Beilstein J. Org. Chem. 2021, 17, 2340–2347, doi:10.3762/bjoc.17.152

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  • furnishing the central ring through CC bond formation. Indeed, this strategy has been employed for decades in reactions such as dehydrative cyclization of acyl-O-aminobiphenyls at very high temperatures (the Pictet–Hubert reaction and Morgan–Walls reaction) [5][6], which is also reflected in modern methods
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Published 08 Sep 2021

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

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  • anthracene derivatives 33. The strategy involved a palladium(II)-catalyzed tandem transformation with diphenyl carboxylic acids 31 and acrylates 32 (Scheme 7) [41]. This new methodology involved a carboxyl-directed C–H alkenylation, a carboxyl-directed secondary C–H activation, an intramolecular CC-bond
  • formation, and further decarboxylative aromatization. The authors used several diphenyl carboxylic acids bearing electron-donating and electron-withdrawing groups on the aromatic rings to produce the corresponding substituted anthracenes, such as compounds 33a–f, in good yields [41]. Recently, Kim and co
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Published 10 Aug 2021

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

  • Renato L. Carvalho,
  • Amanda S. de Miranda,
  • Mateus P. Nunes,
  • Roberto S. Gomes,
  • Guilherme A. M. Jardim and
  • Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

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Published 30 Jul 2021

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

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  • cyclization, Scheidt and co-workers introduced a new method to access highly functionalized chiral THP efficiently (Scheme 17) [52]. Furthermore, the possible reaction pathway indicates the formation of oxocarbenium ion 82, followed by CC bond formation via a chair-like transition state to afford 83 (Scheme
  • DDQ and the subsequent abstraction of hydride from the benzylic or allylic position generated a charge-transfer complex 298. The complex 298 formed a tin-containing ate oxocarbenium ion complex 299 with SnBr4, and then rapid CC bond formation took place to generate the cyclic intermediate 300. The
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Published 29 Apr 2021

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

  • Zhonglie Yang,
  • Yutong Liu,
  • Kun Cao,
  • Xiaobin Zhang,
  • Hezhong Jiang and
  • Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

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  • conditions, more attention has been paid to this efficient strategy for CC-bond formation. In 2015, Yu and colleagues [27] proposed a method for direct C–H trifluoromethylation of aromatic hydrocarbons through an EDA complex. Trifluoromethylated product 61 was synthesized by employing tryptamine derivative
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Published 06 Apr 2021

Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH]

  • Takeshi Fujita,
  • Noriaki Shoji,
  • Nao Yoshikawa and
  • Junji Ichikawa

Beilstein J. Org. Chem. 2021, 17, 396–403, doi:10.3762/bjoc.17.35

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  • bisacetal precursors, which were readily prepared through CC bond formation by Suzuki–Miyaura coupling. This cyclization was efficiently realized by a catalytic amount of trifluoromethanesulfonic acid (TfOH) in a cation-stabilizing solvent, 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), which readily allowed
  • derivatives readily underwent intramolecular Friedel–Crafts-type CC bond formation followed by dehydration or alcohol elimination, leading to the construction of benzene rings in the biaryl systems (Scheme 2) [20][21]. The reaction proceeded via oxocarbenium ion intermediates stabilized by HFIP. This method
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Published 09 Feb 2021

All-carbon [3 + 2] cycloaddition in natural product synthesis

  • Zhuo Wang and
  • Junyang Liu

Beilstein J. Org. Chem. 2020, 16, 3015–3031, doi:10.3762/bjoc.16.251

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  • cation, which is intercepted by the titanium enolate and results in the new CC bond formation to give the five-membered carbocycle 169. Conclusion The all-carbon [3 + 2] cycloaddition, together with the [3 + 2] annulation, continue to be an attractive class of reactions for the synthesis of highly
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Published 09 Dec 2020

Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis

  • David Van Craen,
  • Jenny Begall,
  • Johannes Großkurth,
  • Leonard Himmel,
  • Oliver Linnenberg,
  • Elisabeth Isaak and
  • Markus Albrecht

Beilstein J. Org. Chem. 2020, 16, 2338–2345, doi:10.3762/bjoc.16.195

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  • providing the stereoinformation necessary for induction during the CC bond formation. Catalytic approaches for C–C bond-forming reactions even found their way into the relatively young field of supramolecular chemistry, e.g., regioselective Diels–Alder reactions within supramolecular hosts as described by
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Published 24 Sep 2020

Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K2S2O8

  • Qiang Liu,
  • Weibang Lu,
  • Guanqun Xie and
  • Xiaoxia Wang

Beilstein J. Org. Chem. 2020, 16, 1974–1982, doi:10.3762/bjoc.16.164

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  • under metal-free conditions and uses cheap K2S2O8 as oxidant with easy handling and a broad substrate scope. The reaction proceeds through a radical phosphinoylation–cyclization via a tandem C–P and CC-bond formation. Biologically active compounds featuring the chroman-4-one framework. X-ray structure
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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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Published 21 Jul 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

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  • formed by an intramolecular C–C or C–N bond-formation event, as detailed in the following. 2.1 Synthesis of phenanthridines via photocatalyzed intramolecular CC bond formation A typical approach makes use of imidoyl radicals [30][44] as the key intermediates. Among the different methods proposed to
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Published 25 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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  • , the ability of transition metal complexes to intercept alkyl radicals has been exploited for expanding the possibility of CC bond formation reactions to cross-couplings. In all of these transformations, the substituents on the alkyl radical determine if it reacts as a nucleophile or an electrophile
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Published 29 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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  • metal-organic (MOF) and covalent-organic frameworks (COF), have significantly expanded the use of these compounds in photoredox catalysis due to the singular electronic features of these materials and chemical robustness as catalysts. The appearance of porphyrins as photoredox catalysts for CC bond
  • formation started in 2016 with the report from Gryko’s group on the photoredox α-alkylation of aldehydes with diazo compounds using 1 mol % of TPP or ZnTPP as photocatalyst [10] (Scheme 1), thus obtaining functionalized aldehydes in 47–90% yields. These results are similar to those previously reported by
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Published 06 May 2020

Copper catalysis with redox-active ligands

  • Agnideep Das,
  • Yufeng Ren,
  • Cheriehan Hessin and
  • Marine Desage-El Murr

Beilstein J. Org. Chem. 2020, 16, 858–870, doi:10.3762/bjoc.16.77

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  • phenols, ketones and 1,3-dienes (Scheme 6) [27]. CC bond formation Complexes of radical and redox-active ligands with transition metals are known to be able to promote radical reactions through single-electron transfer (SET) processes [28]. Expanding on the research area pioneered by Wieghardt and
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Published 24 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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  • methods for CC bond formation at the α position of these amines have been studied under photoredox catalysis (Scheme 1) [23][24][25][26]. Among the functionalized THIQs, 1-benzyl-substituted analogues were shown to be able to modulate Ca/K channels, and the synthesis of these compounds is therefore of
  • . Further investigations in this direction are ongoing in our labaratories. Kinetic profile for the benzylation of 1 to 3. Examples of photocatalytic CC bond formation by nucleophilic trapping of a reactive THIQ intermediate. Benzylation of N-phenyl-THIQ. Benzylation of substituted N-arylTHIQs. Removal of
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Published 21 Apr 2020

Reaction of indoles with aromatic fluoromethyl ketones: an efficient synthesis of trifluoromethyl(indolyl)phenylmethanols using K2CO3/n-Bu4PBr in water

  • Thanigaimalai Pillaiyar,
  • Masoud Sedaghati and
  • Gregor Schnakenburg

Beilstein J. Org. Chem. 2020, 16, 778–790, doi:10.3762/bjoc.16.71

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  • advantages of this protocol. Keywords: CC-bond formation; C3-funtionalization of indole; diindolylmethane; Friedel–Crafts reaction; indole; indole-3-carbinol; large-scale synthesis; recyclability; Introduction (1H-Indol-3-yl)methanols have emerged as versatile pre-electrophiles for C–C functionalization
  • makes a hydrogen bond interaction with the NH of the 5-methoxyindole (1a) and form the adduct B. This interaction assists 1a reacting with an electrophilic ketone (2a) to form the intermediate D via CC bond formation (C). Re-aromatization of D generates E, which then protonates to form the desired
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Published 20 Apr 2020
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