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Search for "acetanilides" in Full Text gives 11 result(s) in Beilstein Journal of Organic Chemistry.

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

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  • 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
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Published 27 Sep 2023

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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  • et al., allowing the synthesis of N-heterocycles such as indoles and pyrroles. The targeted heterocyclic products were obtained by cyclization of acetanilides with alkyne derivatives via a direct ortho-metalation pathway (Figure 17) [79]. Acetyl substituents acted as DG in this transformation
  • independently published alternative procedures based on the same dual catalytic system merging C–H activation and photoredox catalysis. In 2017, Xu’s group reported a variation of the ortho-arylation of acetanilides and benzamides with aryldiazonium salts [84], now compatible with a cheaper photosensitizer, i.e
  • out at room temperature, promoted the introduction of various aromatic as well as aliphatic acyl motifs and was applicable to a broad range of substrates hence furnishing more than 30 acylated acetanilides in good to excellent yields. The proposed mechanism involves an initial amide-directed C–H
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Published 21 Jul 2020

Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

  • Rafia Siddiqui and
  • Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

Graphical Abstract
  • Figure 3, E0,0 is the energy gap between the ground state and the lowest triplet state, corresponding to the band gap in semiconductors. C–H acylation Decarboxylative acylation of acetanilides: In 2015, Wang and co-workers first reported the acylation of acetanilides via C–H functionalization using
  • olefination. C–H olefination of phenolic ethers. Decarboxylative acylation of acetanilides. Synthesis of fluorenone derivatives by intramolecular deoxygenative acylation of biaryl carboxylic acids. Synthesis of benzothiazoles via aerobic C–H thiolation. Synthesis of benzothiazoles via oxidant-free C–H
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Published 26 Feb 2020

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

  • Xiaowei Li,
  • Xiaolin Shi,
  • Xiangqian Li and
  • Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

Graphical Abstract
  • efficient method to access ortho-CF3 acetanilides and anilines (Scheme 66b). Recently, Wang and co-workers [127] reported a visible-light-induced Pd-catalyzed ortho-trifluoromethylation of acetanilides. Without the need of an external photocatalyst and additive, various N-substituted anilides and
  • acetanilides were obtained efficiently at room temperature in air. The strategy features good yields, broad functional group tolerance and high regioselectivity (Scheme 67). Copper-catalyzed trifluoromethylation of aryl- and alkenylboronic acids: In 2011, Liu and Shen [128] developed a CuI-catalyzed method for
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Published 23 Sep 2019

A challenging redox neutral Cp*Co(III)-catalysed alkylation of acetanilides with 3-buten-2-one: synthesis and key insights into the mechanism through DFT calculations

  • Andrew Kenny,
  • Alba Pisarello,
  • Arron Bird,
  • Paula G. Chirila,
  • Alex Hamilton and
  • Christopher J. Whiteoak

Beilstein J. Org. Chem. 2018, 14, 2366–2374, doi:10.3762/bjoc.14.212

Graphical Abstract
  • relative infancy and often transferability between substrate classes remains unresolved and limitations not fully understood. This study focuses on the translation of an established Cp*Co(III)-catalysed alkylation of benzamides to related acetanilides using 3-buten-2-one as coupling partner. The developed
  • procedure provides a wide substrate scope in terms of substituted acetanilides, although the optimised conditions were found to be more forcing than those for the corresponding benzamide substrates. Interestingly, density functional theory (DFT) studies reveal that the major impediment in the mechanism is
  • not the C–H activation step, but instead and unexpectedly, effective competition with more stable compounds (resting states) not involved in the catalytic cycle. Keywords: acetanilides; alkylation; C–H activation; cobalt catalysis; DFT studies; Introduction Controlled functionalisation of ubiquitous
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Published 10 Sep 2018

Palladium-catalyzed ortho-halogenations of acetanilides with N-halosuccinimides via direct sp2 C–H bond activation in ball mills

  • Zi Liu,
  • Hui Xu and
  • Guan-Wu Wang

Beilstein J. Org. Chem. 2018, 14, 430–435, doi:10.3762/bjoc.14.31

Graphical Abstract
  • . China 10.3762/bjoc.14.31 Abstract A solvent-free palladium-catalyzed ortho-iodination of acetanilides using N-iodosuccinimide as the iodine source has been developed under ball-milling conditions. This present method avoids the use of hazardous organic solvents, high reaction temperature, and long
  • reaction time and provides a highly efficient methodology to realize the regioselective functionalization of acetanilides in yields up to 94% in a ball mill. Furthermore, the current methodology can be extended to the synthesis of ortho-brominated and ortho-chlorinated products in good yields by using the
  • ], we have independently investigated the solvent-free ortho-iodination of acetanilides under ball-milling conditions [45]. In addition, the current reaction can be extended to ortho-bromination and ortho-chlorination by using the corresponding N-halosuccinimides. Herein, we report these regioselective
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Published 16 Feb 2018

CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na

  • Hélène Guyon,
  • Hélène Chachignon and
  • Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

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  • synthesis of modified nucleosides, in particular 8-CF3-2’-deoxyguanosine and 8-CF3-inosine in 39 and 73% yields, respectively [58]. The same copper-free method was applied for the trifluoromethylation of a variety of electron-deficient 4-substituted acetanilides or anilines (Scheme 36). In these reaction
  • conditions, Cao’s group reported that acetanilides or anilines featuring electron-donating substituents at the para-position of the acetamino group afforded mixtures of isomeric C−H trifluoromethylation products in moderate yields. However, with substrates bearing electron-withdrawing groups, ortho-CF3
  • acetanilides or anilines were obtained as sole products [59]. To meet high expectations of environmentally low impact chemical reactions, Lipshutz and co-workers carried out the trifluoromethylation of heterocycles using aqueous micellar conditions based on the surfactant TPGS−750−M in water at room
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Published 19 Dec 2017

New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

  • Pavel Nagorny and
  • Zhankui Sun

Beilstein J. Org. Chem. 2016, 12, 2834–2848, doi:10.3762/bjoc.12.283

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  • co-workers explored the use of α-halogenated acetanilides L14 and L15 as hydrogen-bonding organocatalysts that activate the carbonyl functionality of lactide and thus enhance their reactivity toward ROP (Scheme 11). In addition to their ability to form more conventional N–H hydrogen bonds, L14 and
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Published 23 Dec 2016

TBHP-mediated highly efficient dehydrogenative cross-oxidative coupling of methylarenes with acetanilides

  • Cui Chen,
  • Weibing Liu and
  • Peng Zhou

Beilstein J. Org. Chem. 2016, 12, 2250–2255, doi:10.3762/bjoc.12.217

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  • has been developed for the synthesis of N-arylbenzamides from methylarenes and acetanilides. This cross-coupling method is free of transition metal catalysts and ligands, and no extra organic solvents are required, which make it an useful and attractive strategy for the straightforward construction of
  • are rather limited, and which would be an important complement to the conventional C–N forming strategies. Herein, we disclose a dehydrogenative C–N cross-oxidative-coupling reaction of methylarenes with acetanilides, using TBHP as an oxidant to afford N-arylamides in moderate to good yields (Scheme 1
  • this transformation. As detailed in Table 2, a wide variety of acetanilides having substituent groups such as methyl, methoxy, ethoxyl, chloro and cyano at different positions were employed to react under the standard conditions. We were pleased to find that all these tested substrates were
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Published 25 Oct 2016

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

  • Igor B. Krylov,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

Graphical Abstract
  • ortho-alkoxylation of arylnitriles 19–20 [48], N-methoxybenzamides 21 [49], and acetanilides 22 [50] and in the ortho-acetoxylation of acetanilides 22 [51] and sulfoximines 23 [52] to prepare cross-dehydrogenative C–O coupling products 24–30 (Scheme 6). The alkoxylation of 1-naphthonitrile 20 occurs not
  • [55], and O-acetyl aryl oximes [56] in the presence of the Pd(OAc)2/PhI(OAc)2 system were described. The ruthenium-catalyzed ortho-acyloxylation of acetanilides 39 with carboxylic acids in the presence of AgSbF6 and ammonium persulfate afforded products 40 (Scheme 8) [57]. This method can be used for
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Published 20 Jan 2015

Recent advances in transition metal-catalyzed Csp2-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

  • Grégory Landelle,
  • Armen Panossian,
  • Sergiy Pazenok,
  • Jean-Pierre Vors and
  • Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

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  • , in the presence or not of the amide additive and of Cu(OAc)2 (Scheme 5). These results confirmed the indispensable involvement of these additives in the mechanism. A complementary study by Z.-J. Shi and coworkers investigated the trifluoromethylation of acetanilides also using palladium(II) and
  • ). Striking features of the reaction were the ability to use alkoxycarbonyl-, benzoyl, acetyl- and acetoxy-substituted acetanilides, and, above all, halogenated arenes including fluoro-, chloro-, bromo- and iodoacetanilides, rendering further functionalization possible. However, the presence of a methoxy or
  • acetanilides by Z.-J. Shi et al., a copper-catalyzed process was developed by C. Chen and C. Xi and colleagues for the functionalization of pivanilides [84]. The latter methodology is simpler and more atom-economical since it does not require additives such as PivOH or stoichiometric metal salts as oxidants
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Published 15 Nov 2013
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