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Search for "halogens" in Full Text gives 129 result(s) in Beilstein Journal of Organic Chemistry.

Oxetanes: formation, reactivity and total syntheses of natural products

  • Peter Gabko,
  • Martin Kalník and
  • Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

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  • halogens, nitriles, alkenes and heteroaryls. On the other hand, this methodology suffers from relatively low diastereoselectivity as the dr lies between 1:1 and 2:1. DFT calculations suggested the reaction proceeds through nitrogen elimination, oxonium ylide 119 formation, homolytic cleavage and radical
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Published 27 Jun 2025

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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  • methoxy (-OMe) and halogens (-F, -Cl, -Br), as well as electron-withdrawing functionalities like trifluoromethyl (-CF₃) and ester groups (-CO₂Me). However, highly electron-deficient substrates, such as those bearing cyano (-CN) or nitro (-NO₂) groups, did not react. Additionally, the study explored
  • functional group tolerance. Various N-arylacrylamides bearing electron-donating and electron-withdrawing groups on the aryl ring reacted smoothly, affording the corresponding halogenated oxindoles 90a–e in moderate to high yields. Substituents such as alkyl, methoxy, halogens (Cl, F, Br), and esters were
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Published 24 Jun 2025

On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals

  • Daniel Straub,
  • Markus Gross,
  • Mona E. Arnold,
  • Julia Zolg and
  • Alexander J. C. Kuehne

Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80

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  • Gomberg (see TTM and PTM in Figure 1a) [31]. Gomberg’s radical emits light in the green region of the visible spectrum, which is shifted bathochromically by substituting the ortho- and para-positions of the trityl phenyl rings with halogens. However, all symmetrical halo-trityl radicals exhibit low ϕ
  • the excited state dynamics, there is evidence for this fast relaxation in donor-functionalized TTM radicals [26]. Moreover, transient absorption has been employed to elucidate the formation of a non-luminescent side-product in trityl radicals. During photodegradation, two halogens are lost and two
  • improved photostability (see Figure 1a). While the triaryl oxyether-TTM does not enhance the ϕ, triaryl thioether-TTM exhibits a ϕ of up to 37.5% (in cyclohexane). Due to the stronger electron donating effect of the chalcogens compared to halogens, the emission is shifted to lower energies with λem = 625
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Published 21 May 2025

Harnessing tethered nitreniums for diastereoselective amino-sulfonoxylation of alkenes

  • Shyam Sathyamoorthi,
  • Appasaheb K. Nirpal,
  • Dnyaneshwar A. Gorve and
  • Steven P. Kelley

Beilstein J. Org. Chem. 2025, 21, 947–954, doi:10.3762/bjoc.21.78

Graphical Abstract
  • alkene side product, presumably arising from mesylate elimination (Table 4, entry 4). In general, the functional group tolerance of the reaction was good, and aryl halogens, aryl CF3 moieties, and benzyl ethers were fully compatible (Table 4, entries 7 and 8). Where applicable, stereoarrays could be
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Published 19 May 2025

Silver(I) triflate-catalyzed post-Ugi synthesis of pyrazolodiazepines

  • Muhammad Hasan,
  • Anatoly A. Peshkov,
  • Syed Anis Ali Shah,
  • Andrey Belyaev,
  • Chang-Keun Lim,
  • Shunyi Wang and
  • Vsevolod A. Peshkov

Beilstein J. Org. Chem. 2025, 21, 915–925, doi:10.3762/bjoc.21.74

Graphical Abstract
  • substrates 15e–l was tested. The process proceeded efficiently in all cases, yielding pyrazolodiazepines 16e–l and demonstrating tolerance for various substituents on the aniline-derived aromatic fragment, including alkyl, halogens, electron-donating alkoxy groups, as well as electron-withdrawing
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Published 08 May 2025

Recent advances in the electrochemical synthesis of organophosphorus compounds

  • Babak Kaboudin,
  • Milad Behroozi,
  • Sepideh Sadighi and
  • Fatemeh Asgharzadeh

Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61

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  • . The reaction was carried out in an undivided cell with a graphite rod electrode as the anode and platinum as the cathode at a constant current of 7.5 mA under N2 for 4 h. Thiophenes with strong electron-withdrawing groups, and halogens produced moderate yields. However, a good yield was achieved when
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Published 16 Apr 2025

Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory

  • Misato Suganuma,
  • Daichi Kitagawa,
  • Shota Hamatani and
  • Seiya Kobatake

Beilstein J. Org. Chem. 2025, 21, 242–252, doi:10.3762/bjoc.21.16

Graphical Abstract
  • time scale [54]. Langton and co-workers demonstrated that the thermal isomerization rate of azobenzenes can be tuned over a time scale spanning 107 seconds by introducing appropriate chalcogens and halogens at the ortho-position of the benzene rings [55]. Thus, investigation of the strategies to
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Published 31 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

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  • –heteroatom (C–X, where X = N, O, or halogens) bonds in organic synthesis. Copper was one of the first transition metals employed in cross-coupling to form C–C and C–X bonds [1][2]. In 1901, Ullmann reported the first cross-coupling reaction for the formation of biaryl compounds in the presence of
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Published 16 Jan 2025

Hypervalent iodine-mediated intramolecular alkene halocyclisation

  • Charu Bansal,
  • Oliver Ruggles,
  • Albert C. Rowett and
  • Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 3113–3133, doi:10.3762/bjoc.20.258

Graphical Abstract
  • , the intramolecular HVI-mediated halocyclisation of alkenes using carbon, oxygen, nitrogen or sulfur nucleophiles. Herein, we describe the examples reported in the literature, which are organised by the different halogens involved and the internal nucleophiles. Keywords: cyclisation; halogenation
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Published 28 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

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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
  • diaryliodonium salts regardless of their differing counter-anions. A range of 2-naphthol substrates, including those bearing alkyl and aryl groups, halogens, trimethylsilyl, and protected hydroxy at positions 6 and 7, exhibited good tolerance. However, the reaction with 1-naphthol did not yield positive results
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Published 13 Nov 2024

C–H Trifluoromethylthiolation of aldehyde hydrazones

  • Victor Levet,
  • Balu Ramesh,
  • Congyang Wang and
  • Tatiana Besset

Beilstein J. Org. Chem. 2024, 20, 2883–2890, doi:10.3762/bjoc.20.242

Graphical Abstract
  • ). Hydrazones derived from aromatic aldehydes (1a–p) were first investigated. It turned out that para-substituted compounds with electron-rich groups (e.g., OMe, OBn), halogens (Cl, Br, I), and electron-withdrawing groups (e.g., CF3) were smoothly trifluoromethylthiolated. In the same vein, meta- and ortho
  • , alkenes) and halogens allowing an array of post-functionalization reactions. Finally, the trifluoromethylthiolation of molecules derived from compounds of interest was achieved to illustrate the synthetic utility of the method. Hence, the desired products 2v–x were efficiently isolated. To get more
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Published 12 Nov 2024

Synthesis and cytotoxicity studies of novel N-arylbenzo[h]quinazolin-2-amines

  • Battini Veeraiah,
  • Kishore Ramineni,
  • Dabbugoddu Brahmaiah,
  • Nangunoori Sampath Kumar,
  • Hélène Solhi,
  • Rémy Le Guevel,
  • Chada Raji Reddy,
  • Frédéric Justaud and
  • René Grée

Beilstein J. Org. Chem. 2024, 20, 2592–2598, doi:10.3762/bjoc.20.218

Graphical Abstract
  • recently [18], gave the first target 4a (R = H) in 69% yield. In a similar way, we prepared a designed library with eighteen additional members 4b to 4s (Figure 2) having in the different ortho, meta and para positions either methyl groups, halogens (F, Cl) or methoxy groups. We have also prepared
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Published 14 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

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Published 09 Oct 2024

HFIP as a versatile solvent in resorcin[n]arene synthesis

  • Hormoz Khosravi,
  • Valeria Stevens and
  • Raúl Hernández Sánchez

Beilstein J. Org. Chem. 2024, 20, 2469–2475, doi:10.3762/bjoc.20.211

Graphical Abstract
  • efficient solvent for synthesizing resorcin[n]arenes in the presence of catalytic amounts of HCl at ambient temperature and within minutes. Remarkably, resorcinols with electron-withdrawing groups and halogens, which are reported in the literature as the most challenging precursors in this cyclization, are
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Published 02 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

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  • ][3][4][5][6][7]. What about other halogens? Pyran inter-halide analogues of carbohydrates were rarely investigated as new tools in glycobiology [8]. This is surprising since the incorporation of halogens can improve cellular uptakes and enhance membrane binding and permeation [9][10][11]. In addition
  • approach from levoglucosan 1 (Figure 1a) [23]. Allopyranose inter-halides 4 incorporating the 2,3-cis, 3,4-cis relationship for the halogens were prepared via intermediates 2 and 3 from levoglucosan (1). Compounds 4 were the starting point to complex 2,3,4-trihalohexanetriols and 2,3,4,5
  • ][25][26][27][28][29][30], such as the solution-state conformation of diastereomeric polyfluorohexitols [31]. Herein, we report the synthesis of pyran inter-halide analogues of ᴅ-talopyranose 6, integrating also the 2,3-cis, 3,4-cis relationship for the halogens, from known intermediate 5 (Figure 1b
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Published 27 Sep 2024

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

  • Akiya Ogawa and
  • Yuki Yamamoto

Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182

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  • the combination with groups 15–17 interelement compounds would be considered effective for the generation of groups 13 and 14 heteroatom radicals. Radical addition of group 17 compounds to isocyanides If isocyanides (RNC) can undergo a radical addition of hydrogen halides (HX) and molecular halogens
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Published 26 Aug 2024

From perfluoroalkyl aryl sulfoxides to ortho thioethers

  • Yang Li,
  • Guillaume Dagousset,
  • Emmanuel Magnier and
  • Bruce Pégot

Beilstein J. Org. Chem. 2024, 20, 2108–2113, doi:10.3762/bjoc.20.181

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  • -position of the nitrile is also detrimental to the reaction, resulting in less than 30% yield of the desired product 3d. Nevertheless, the reaction is compatible with halogens elsewhere in longer nitrile alkyl chains (3e,g). Finally, it was possible to obtain the terminal alkene 3f with a yield of 58
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Published 23 Aug 2024

A comparison of structure, bonding and non-covalent interactions of aryl halide and diarylhalonium halogen-bond donors

  • Nicole Javaly,
  • Theresa M. McCormick and
  • David R. Stuart

Beilstein J. Org. Chem. 2024, 20, 1428–1435, doi:10.3762/bjoc.20.125

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  • we include the halogens Cl, Br, I, and At. Within this diverse set of halogen-bond donors, we have found trends that relate halogen bond length with the van der Waals radii of the halogen and the non-covalent or partial covalency of the halogen bond. We have also developed a model to calculate ΔG of
  • Discussion This study evolved from a parallel exploration of reactions involving unsymmetrical phenyl(mesityl)halonium salts, i.e., Ph(Mes)X+. DFT analysis revealed similar structural trends to our previous work [21] when we expanded the halogens to include astatine (At). Due to its radioactivity and short
  • ]. Smaller halogens that are less able to disperse lone-pairs may have greater destabilizing repulsive forces associated with them that ultimately lengthen the halogen bond relative to those of larger halogens [22][40]. Further analysis of the XB complexes revealed additional distinctions in the nature of
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Published 27 Jun 2024

Hypervalent iodine-catalyzed amide and alkene coupling enabled by lithium salt activation

  • Akanksha Chhikara,
  • Fan Wu,
  • Navdeep Kaur,
  • Prabagar Baskaran,
  • Alex M. Nguyen,
  • Zhichang Yin,
  • Anthony H. Pham and
  • Wei Li

Beilstein J. Org. Chem. 2024, 20, 1405–1411, doi:10.3762/bjoc.20.122

Graphical Abstract
  • substrate scope using 3,4-dimethylbenzamide, which afforded the oxazoline product 17 in 70% yield (Figure 3). Based on this optimal amide structure, we examined various electronically activated olefins under the optimal reaction conditions. A number of styrenyl derivatives with para-substituted halogens
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Published 24 Jun 2024

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

  • Mohd Farhan Ansari,
  • Atul Kumar Maurya,
  • Abhishek Kumar and
  • Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

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  • methanol was achieved at 100 °C with one equivalent of t-BuOK. In all the cases, the catalytic system selectively yielded mono-N-alkylated and N-methylated products under mild conditions. Noteworthy, high functional group tolerance, such as alkenes, halogens, thioethers, and benzodioxane derivatives was
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Published 21 May 2024

Light on the sustainable preparation of aryl-cored dibromides

  • Fabrizio Roncaglia,
  • Alberto Ughetti,
  • Nicola Porcelli,
  • Biagio Anderlini,
  • Andrea Severini and
  • Luca Rigamonti

Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95

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  • be employed in two variants modulated by light irradiation. This external switch can be used to selectively trigger side-chain or core halogenation. Keywords: aryl halides; benzyl halides; bromination; sustainability; Introduction Activation through halogens has become a key strategy in achieving
  • context of covalent organic frameworks (COFs) and metal-organic frameworks (MOFs), frequently assembled through imine linkages. While C–H activation through halogens presents clear technical advantages, it also brings forth concerns about the toxicity of halo compounds to both human health and the
  • for halo compounds, potentially involving the use of eco-friendly halogenation reagents. The development of methods for the efficient removal and recycle of halogens, advocating principles of a circular economy. It is noteworthy that both aspects are influenced by the type of halogen employed. When
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Published 14 May 2024

Carbonylative synthesis and functionalization of indoles

  • Alex De Salvo,
  • Raffaella Mancuso and
  • Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

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  • reaction was run in toluene at 100 °C for 24 h under 20 bar of CO [56] (Scheme 25). The other example, however, accomplished the synthesis through Rh-catalysis from substrates without halogens in their structure. This synthesis was published by Huang et al. who obtained good results by using [(Cp*RhCl2)2
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Published 30 Apr 2024

Ortho-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins

  • Ke Jiang,
  • Cheng Pan,
  • Limin Wang,
  • Hao-Yang Wang and
  • Jianwei Han

Beilstein J. Org. Chem. 2024, 20, 841–851, doi:10.3762/bjoc.20.76

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  • this reaction, regardless of the electronic nature and position of the substituents. The desired 3,4-benzocoumarin products 3ba–ma were obtained in yields of 21–59%. Notably, substituents such as halogens (F, Cl, and Br), methyl, methoxy, and trifluoromethyl groups at the ortho-, meta-, or para
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Published 18 Apr 2024

(E,Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene

  • Nataliia V. Kirij,
  • Andrey A. Filatov,
  • Yurii L. Yagupolskii,
  • Sheng Peng and
  • Lee Sprague

Beilstein J. Org. Chem. 2024, 20, 452–459, doi:10.3762/bjoc.20.40

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  • -hexafluorobut-2-ene and an oxalamide hydrazone [17]. In the present study, we investigated the reactions of commercially available butenes 1a,b with halogens, as well as subsequent transformations of the resulting compounds. Results and Discussion In 1952 Haszeldine found that the reaction of bromine with (E
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Published 27 Feb 2024
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