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Search for "aryl chlorides" in Full Text gives 46 result(s) in Beilstein Journal of Organic Chemistry.

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

  • Jiangfei Chen,
  • Yi-Lin Qu,
  • Ming Yuan,
  • Xiang-Mei Wu,
  • Heng-Pei Jiang,
  • Ying Fu and
  • Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

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  • halogenated oxindole product. In 2023, Kuniyil and Yatham’s group reported a redox-neutral, metal-free radical cascade cyclization strategy for the functionalization of N-arylacrylamides using unactivated alkyl and aryl chlorides, enabling the efficient construction of 3,3-disubstituted oxindoles 92 under
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Published 24 Jun 2025

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

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  • agrochemical and pharmaceutical chemistry. In 2019, Jiao and colleagues reported that 1,2-dichloroethane (DCE) could be used as a chlorination reagent for the production of (hetero)aryl chlorides and vinyl chlorides [21]. The reactions were carried out in an undivided cell containing a mixture of DCE in
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Published 09 Oct 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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  • formation of alkenone intermediates, dialkyl acetylenedicarboxylates 147, as alkynoyl derivatives, are transformed to pyrazolones 149 by Michael addition–cyclocondensation with phenylhydrazine. In a consecutive one-pot reaction, the latter intermediates undergo O-acylation with aryl chlorides to give N
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Published 16 Aug 2024

Transition-metal-catalyst-free electroreductive alkene hydroarylation with aryl halides under visible-light irradiation

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

Beilstein J. Org. Chem. 2024, 20, 1327–1333, doi:10.3762/bjoc.20.116

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  • ][34][35][36]. In this context, the electrochemical single-electron reduction of aryl iodides, bromides, and activated (bearing at least one electron-withdrawing group) aryl chlorides has been demonstrated as a useful method to generate aryl radical species under mild reaction conditions [37]. Although
  • . Recently, the groups of Lin and Lambert [48] and Wickens [49] independently demonstrated that aryl chlorides with highly negative reduction potentials engaged in C–X (X = P, Sn, B) and C–C bond formation reactions involving aryl radical species by integrating photochemistry and electrochemistry [50][51][52
  • ][53]. Furthermore, odd-numbered [n]cumulenes have proven to be effective redox mediators for electroreductive radical borylation of unactivated aryl chlorides without visible-light irradiation by the group of Milner [54]. Herein, we report transition-metal-catalyst-free electroreductive alkene
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Letter
Published 10 Jun 2024

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

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  • reductants as a theme of ongoing debate [39]. Nonetheless, this protocol enabled the reduction of various electron-poor aryl iodides and aryl bromides and, for the first time, the reduction of aryl chlorides (albeit electron-poor ones) via visible light PRC in good to excellent yields (35–98%) (Figure 4A
  • infra, Figure 69), the Wickens group developed a conPET protocol using 2,4,5,6-tetrakis(diphenylamino)isophthalonitrile (4-DPAIPN) for the reduction of electron-rich aryl chlorides [55]. With 4-DPAIPN as an electron-primed photocatalyst, substrates with reduction potentials as deep as Epred = −3.4 V vs
  • hydroarylation of tert-butyl vinylcarbamate and unactivated alkenes like 1-octene and 3-buten-1-ol although the vinyl carbamate substrate (Epred = −2.2 V vs SCE) is significantly easier to reduce than most aryl chlorides. This selectivity, especially considering the need for an excess of the vinyl carbamate
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Published 28 Jul 2023

Total synthesis of insect sex pheromones: recent improvements based on iron-mediated cross-coupling chemistry

  • Eric Gayon,
  • Guillaume Lefèvre,
  • Olivier Guerret,
  • Adrien Tintar and
  • Pablo Chourreu

Beilstein J. Org. Chem. 2023, 19, 158–166, doi:10.3762/bjoc.19.15

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  • combination with a variety of alkenyl chlorides and (hetero)aryl chlorides [18]. Importance of the leaving groups: use of enol phosphates In order to overcome the delicate choice of either NMP or one of its surrogates as a suitable co-solvent, it has also been demonstrated that amide-free catalytic procedures
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Published 14 Feb 2023

Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry

  • Koji Kubota,
  • Emiru Baba,
  • Tamae Seo,
  • Tatsuo Ishiyama and
  • Hajime Ito

Beilstein J. Org. Chem. 2022, 18, 855–862, doi:10.3762/bjoc.18.86

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  • halides in a test tube [15]. They found that a Pd(dba)2/DPEphos catalytic system was effective for aryl bromides, and aryl chlorides reacted more efficiently when XPhos was used as the ligand [15]. Although their achievements are remarkable, this protocol is only applicable to liquid substrates, which can
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Published 18 Jul 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

Graphical Abstract
  • higher reactivity and less active aryl chlorides were successfully coupled to give the desired products in acceptable yields. The reaction carried out by both catalysts gave excellent yields of up to 98% for Co-NHC@MWCNTs and a still good yield of up to 91% for reactions catalyzed by Co-NPs. It was
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Published 03 Mar 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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  • classically sensitive functionalities like esters and aryl chlorides. Exposure of the iron catalyst to one equivalent of aryl Grignard reagent 2b in the absence of the halide substrate afforded the bimetallic Fe(II) complex FeBr2[Mg(acac)2](THF)2. Using FeBr2[Mg(acac)2](THF)2 in place of Fe(acac)3 in the
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Published 07 Dec 2021

Photoredox catalysis in nickel-catalyzed C–H functionalization

  • Lusina Mantry,
  • Rajaram Maayuri,
  • Vikash Kumar and
  • Parthasarathy Gandeepan

Beilstein J. Org. Chem. 2021, 17, 2209–2259, doi:10.3762/bjoc.17.143

Graphical Abstract
  • arylation of cyclic and acyclic ethers 9 with aryl chlorides 8 under photoredox nickel catalysis (Scheme 5) [56]. Here, aryl chlorides 8 serve as cross-coupling partners and the chlorine radical source, which rapidly abstracts an α-oxy C(sp3)−H of the ethers to form the key α-oxyalkyl radical intermediate
  • of aryl chlorides 8 through selective 2-functionalization of 1,3-dioxolane (13) followed by a mild acidic workup (Scheme 9) [61]. Here, the photocatalyst Ir[dF(CF3)ppy]2(dtbbpy)PF6 and nickel catalyst NiCl2·DME with dtbbpy as ligand, along with K3PO4 as base under irradiation with blue LEDs enabled
  • the regioselective 2-functionalization of 1,3-dioxolane (13) with aryl chlorides 8. It was found that the electron-deficient aryl chlorides resulted in better yields within shorter reaction times over the electron-rich substrates. A possible catalytic cycle was shown to account for the reaction mode
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Published 31 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

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

Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides

  • Mateo Berton,
  • Kevin Sheehan,
  • Andrea Adamo and
  • D. Tyler McQuade

Beilstein J. Org. Chem. 2020, 16, 1343–1356, doi:10.3762/bjoc.16.115

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  • well-packed column: 98%. System scope: Next, we probed the limit of this transformation for primary (bromoethane, bromooctane, chlorobutane, and iodomethane) and secondary (2-bromopropane, 2-chloropropane, and 2-chlorobutane) alkyl halides as well as benzyl (chloromethylbenzene) and aryl chlorides
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Published 19 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

Graphical Abstract
  • the nature of the halide: as a trend, aryl iodides are easier to reduce than aryl bromides and aryl chlorides [67][77]. Under organophotocatalytic conditions, the reduction can be achieved following two main strategies for accessing stronger reduction potentials: (a) tuning the electronics of the
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Published 29 May 2020

Recent advances in Cu-catalyzed C(sp3)–Si and C(sp3)–B bond formation

  • Balaram S. Takale,
  • Ruchita R. Thakore,
  • Elham Etemadi-Davan and
  • Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

Graphical Abstract
  • conditions, a rare cross-coupling takes place (Scheme 62) [115]. The cooperative effect of a catalytic system consisting of Cu/Ni (e.g., Ni(acac)2, CuCl, and PCy3) was also reported by Nakao et al. leading to regio- and stereoselective arylboration of 1-arylalkenes with aryl chlorides or tosylates. The
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Published 15 Apr 2020

Regioselective Pd-catalyzed direct C1- and C2-arylations of lilolidine for the access to 5,6-dihydropyrrolo[3,2,1-ij]quinoline derivatives

  • Hai-Yun Huang,
  • Haoran Li,
  • Thierry Roisnel,
  • Jean-François Soulé and
  • Henri Doucet

Beilstein J. Org. Chem. 2019, 15, 2069–2075, doi:10.3762/bjoc.15.204

Graphical Abstract
  • , but in low yields due to a partial conversion of these aryl bromides. It should be mentioned that the use of aryl chlorides instead of aryl bromides did not allow to improve the regioselectivities or the reaction yields. With 4-chlorobenzonitrile, product 2 was obtained in 80% regioselectivity and in
  • 38% yield; whereas the use of 2-chlorobenzonitrile afforded 12 in 62% regioselectivity and in 34% yield. In both cases, partial conversions of the aryl chlorides were observed. Pyridines and quinoline heterocycles are very important structures in pharmaceutical chemistry as more than 100 currently
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Published 29 Aug 2019

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

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Published 19 Jul 2019

Selective benzylic C–H monooxygenation mediated by iodine oxides

  • Kelsey B. LaMartina,
  • Haley K. Kuck,
  • Linda S. Oglesbee,
  • Asma Al-Odaini and
  • Nicholas C. Boaz

Beilstein J. Org. Chem. 2019, 15, 602–609, doi:10.3762/bjoc.15.55

Graphical Abstract
  • intractable products, which were in many cases polyfunctionalized. Additionally, substrates containing arene rings were shown to inhibit aliphatic C–H functionalization via electrophilic trapping of reactive halogen species to form aryl chlorides and iodides. Utilizing NHPI as a less reactive hydrogen atom
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Published 05 Mar 2019

Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source

  • Tetsuaki Fujihara and
  • Yasushi Tsuji

Beilstein J. Org. Chem. 2018, 14, 2435–2460, doi:10.3762/bjoc.14.221

Graphical Abstract
  • carboxylation of aryl halides and pseudohalides using CO2 is an important reaction to yield benzoic acid derivatives. In 2009, Martin reported the Pd-catalyzed carboxylation of aryl bromides using ZnEt2 as the reductant [31]. In 2012, we first reported the Ni-catalyzed carboxylation of aryl chlorides and vinyl
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Published 19 Sep 2018

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

  • Michael K. Bogdos,
  • Emmanuel Pinard and
  • John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

Graphical Abstract
  • the presence of triethylamine (Scheme 5) [46]. The biggest breakthrough in this case is the excitation of PDI by two photons, creating a radical anion in an excited state, giving the catalyst a much higher reducing power, allowing the reduction of aryl chlorides (see product 5b). This is the first
  • report of the reduction of aryl chlorides without the use of a strong base, UV radiation or highly reactive neutral organic reducing agents. The PDI catalytic cycle is different to the general catalytic cycle presented in the introduction and is presented in Figure 7. The group also showed that it is
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Published 03 Aug 2018

Water-soluble SNS cationic palladium(II) complexes and their Suzuki–Miyaura cross-coupling reactions in aqueous medium

  • Alphonse Fiebor,
  • Richard Tia,
  • Banothile C. E. Makhubela and
  • Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1859–1870, doi:10.3762/bjoc.14.160

Graphical Abstract
  • . By using only 0.5 mol % loading of the complexes, the coupling of inactivated aryl bromides and activated aryl chlorides with various boronic acids in water was achieved in excellent yields and the catalysts were found to be reusable for three cycles without a significant loss of activity. The
  • ; but required stoichiometric amounts of tetra-n-butylammonium bromide (TBAB) to effect the reaction of inactivated aryl bromides [35]. A further limitation of these catalysts is their incapability to catalyse the coupling reaction when either activated or inactivated aryl chlorides are employed as
  • . The slightly lower yield of the reaction in the preparation of 23i could be ascribed to steric encumbrance exerted by the NO2-substituent located at the ortho-position of the aryl bromide. Encouraged by these results, the reactivities of aryl chlorides were investigated under the optimised conditions
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Published 23 Jul 2018

Nanoreactors for green catalysis

  • M. Teresa De Martino,
  • Loai K. E. A. Abdelmohsen,
  • Floris P. J. T. Rutjes and
  • Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

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  • quantitative yields were observed when aryl chloride coupling was performed with arylboronic acids. This is indeed remarkable as aryl chlorides are generally not as reactive as aryl bromides or aryl iodides. Lipshutz and Ghorai developed a micellar system called PQS to perform aldol reactions in water [25]. As
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Published 29 Mar 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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Published 19 Dec 2017

Mechanochemical synthesis of small organic molecules

  • Tapas Kumar Achar,
  • Anima Bose and
  • Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

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  • ), phenylboronic acid (2.0 equiv), K2CO3 (3.0 equiv) and Pd(PPh3)4 (5 mol %) resulted in coupled products with 96% yield (Scheme 7). The NaCl was used as an additive to make the reaction mixture sufficiently powdery for uniform mixing. The use of aryl chlorides is generally restricted in Suzuki reactions because
  • of their low reactivity. Recently, Li and Su with co-workers have developed a liquid-assisted grinding (LAG) method for the Suzuki–Miyaura coupling between aryl chlorides and boronic acids to synthesize the biaryls in nearly quantitative yield. Under optimized conditions 2 mol % Pd(OAc)2 and 4 mol
  • of styrenes with aryl bromides or aryl chlorides (Scheme 9) [59]. Sonogashira reaction Stolle and co-workers have reported a Sonogashira coupling reaction under ball milling conditions in which the reactions were done in absence of any copper catalyst or any additional ligands [60]. In presence of
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Published 11 Sep 2017

An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

  • Carolina S. García,
  • Paula M. Uberman and
  • Sandra E. Martín

Beilstein J. Org. Chem. 2017, 13, 1717–1727, doi:10.3762/bjoc.13.166

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  • -position. The coupling of styrene with a substrate bearing an acidic proton, 4-iodophenol (1h), was found to proceed efficiently, obtaining a high TOF of 19920 h−1 (entry 8, Table 2). Unfortunately, it was not possible to successfully accomplish the Mizoroki–Heck coupling with aryl chlorides under many
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Published 18 Aug 2017
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