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Search for "stepwise" in Full Text gives 320 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Advances in nitrogen-containing helicenes: synthesis, chiroptical properties, and optoelectronic applications

  • Meng Qiu,
  • Jing Du,
  • Nai-Te Yao,
  • Xin-Yue Wang and
  • Han-Yuan Gong

Beilstein J. Org. Chem. 2025, 21, 1422–1453, doi:10.3762/bjoc.21.106

Graphical Abstract
  • ), exceptionally high BCPL as 100.2 M−1 cm−1, and marked chiroptical activity (|gabs| = 2.50 × 10−3 at 435 nm; |glum| = 5.00 × 10−3 at 460 nm) (Table 6). Upon mild oxidation, neutral 22 undergoes stepwise conversion into highly charged, multispin open-shell species 222+2• and 224+4•, preserving strong chiroptical
  • for NIR optoelectronic applications. Building on this work, in 2025 the same group reported the synthesis of a stable N-heterotriangulene dimer (compound 30) bridged by a rigid π-conjugated [5]helicene [44]. This chiral dimer undergoes reversible stepwise oxidation to 30•+ and 302+, accompanied by
  • -width (FWHM values as 24 nm and 22 nm). Stepwise titration experiments with fluoride ions induced a change in the coordination number of the boron centers from three to four, forming corresponding anionic species. This coordination triggered red-shifted absorption and CPL responses while maintaining
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Published 11 Jul 2025

Tautomerism and switching in 7-hydroxy-8-(azophenyl)quinoline and similar compounds

  • Lidia Zaharieva,
  • Vera Deneva,
  • Fadhil S. Kamounah,
  • Nikolay Vassilev,
  • Ivan Angelov,
  • Michael Pittelkow and
  • Liudmil Antonov

Beilstein J. Org. Chem. 2025, 21, 1404–1421, doi:10.3762/bjoc.21.105

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  • ). Simulated absorption spectra of the tautomers of 1 in toluene. The spectra in acetonitrile are shown in Figure S1 in Supporting Information File 1. Normalized absorption spectra of 1. Absorption spectra of 1 in acetonitrile with stepwise addition of water. VT 1H NMR spectra of compound 1 in acetonitrile-d3
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Published 10 Jul 2025

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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  • substrate scope revealed that the reaction stereoselectivity is highly dependent on the structure of the ketoester component and tends to be unpredictable. 1.3.2 Formal cycloadditions: These stepwise processes typically take place between an enolate or enol ether and a carbonyl under Lewis acid or base
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Published 27 Jun 2025

Recent advances in amidyl radical-mediated photocatalytic direct intermolecular hydrogen atom transfer

  • Hao-Sen Wang,
  • Lin Li,
  • Xin Chen,
  • Jian-Li Wu,
  • Kai Sun,
  • Xiao-Lan Chen,
  • Ling-Bo Qu and
  • Bing Yu

Beilstein J. Org. Chem. 2025, 21, 1306–1323, doi:10.3762/bjoc.21.100

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  • the photocatalyst [Ir(dF(CF3)ppy)2(4,4'-d(CF3)bpy)]PF6 in combination with a base (NBu4OP(O)(OBu)2) (Scheme 1) [59]. The generation of amidyl radical 5 involved a stepwise PCET process catalyzed by the combined effect, in the presence of photocatalyst and the base. Subsequently, amidyl radical 5
  • these bonds through high selectivity, efficiency, and a stepwise approach. In the presence of amidyl radicals, hydrogen atoms are directly abstracted from C–H, Si–H, Ge–H, and B–H bonds, leading to the formation of corresponding radicals. We summarize and emphasize notable pioneering experiments in this
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Published 27 Jun 2025

Recent advances and future challenges in the bottom-up synthesis of azulene-embedded nanographenes

  • Bartłomiej Pigulski

Beilstein J. Org. Chem. 2025, 21, 1272–1305, doi:10.3762/bjoc.21.99

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  • synthetic strategy was used by Jiang and co-workers for the synthesis of very stable non-alternant nanographene with a triplet ground state [41]. Zhang and co-workers reported the synthesis of diazulenorubicene 29, a non-benzenoid isomer of peri-tetracene (Scheme 5) [42]. The stepwise oxidation of compound
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Published 26 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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Published 24 Jun 2025

Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages

  • Keith G. Andrews

Beilstein J. Org. Chem. 2025, 21, 421–443, doi:10.3762/bjoc.21.30

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  • ][344][345], which show early promise for low-symmetry cavities with catalytic potential [42][43][44][340]. Notably, Otte has used semi-stepwise self-assembly via imine formation/reduction to access a robust organic cage with reduced-symmetry and internal functionality able to chelate a copper(I) ion
  • purification possibilities available for robust organic cages mean access to structural families via stepwise synthesis or statistical methods followed by separation is facile, as demonstrated by Otte [42][43][44] and ourselves [41]. The lack of internal functionality in cavities doesn’t just reduce the
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Published 24 Feb 2025

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

  • Rituparna Das and
  • Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

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  • in attaining the required stereospecific glycosylation outputs. Apart from the widely convenient stepwise synthesis, recently one-pot glycosylations have also made an important mark which minimise the tedious purification of the intermediate molecules in each step [53][54][55][56][57][58]. In the
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Published 17 Feb 2025

Oxidation of [3]naphthylenes to cations and dications converts local paratropicity into global diatropicity

  • Abel Cárdenas,
  • Zexin Jin,
  • Yong Ni,
  • Jishan Wu,
  • Yan Xia,
  • Francisco Javier Ramírez and
  • Juan Casado

Beilstein J. Org. Chem. 2025, 21, 277–285, doi:10.3762/bjoc.21.20

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  • theoretical Raman band at 1730 cm−1. FT-Raman spectra in CH2Cl2 (approx. 10−2 to 10−3 M) of: top) 1 (black), 1•+ (blue), and 12+ (red). Bottom) 2 (black), 2•+ (blue), and 22+ (red). Oxidations are carried out by stepwise addition of NOBF4 in CH2Cl2. Force constants for the CC stretching vibrational
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Published 05 Feb 2025

Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride

  • Laura D’Andrea and
  • Simon Jademyr

Beilstein J. Org. Chem. 2025, 21, 39–46, doi:10.3762/bjoc.21.4

Graphical Abstract
  • reduction can be accomplished via catalytic hydrogenation, involving stepwise reactions and workup, use of additional reagents, and reaction time between 3 and 24 hours [11][12]. Most commonly, metal hydrides are employed, typically lithium aluminum hydride [13][14][15][16][17][18], requiring an inert
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Published 07 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

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  • azadiene in a stepwise mechanism: firstly, the vinylogous Michael addition of the dienolate to the double bond of the α,β-unsaturated N-sulfonylimine occurs in a stereoselective fashion. Subsequently, cyclization due to an intramolecular aza-Michael reaction and protonation leads to the enantioenriched
  • alcohol E isomer and it coordinated to the squaramide in an effective orientation, a stepwise mechanism is taking place. Firstly, the dienolate adds to the azadiene which is followed by cyclization with formation of the C–N bond. Finally, protonation leads to the formation of the desired derivative. The
  • excellent enantioselectivities (70–95% ee) when using chiral phosphoric acid XIV (Scheme 16). Mechanistic studies were performed to unveil whether a concerted or stepwise mechanism is taking place, such as trying to trap a possible iminium ion intermediate. The outcome of those experiments pointed towards a
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Published 10 Dec 2024
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Published 19 Nov 2024

Copper-catalyzed yne-allylic substitutions: concept and recent developments

  • Shuang Yang and
  • Xinqiang Fang

Beilstein J. Org. Chem. 2024, 20, 2739–2775, doi:10.3762/bjoc.20.232

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  • , 50a–l) axial chirality in remarkable enantiopurities. Mechanistic studies and deuterium labeling experiments have revealed that the reaction proceeds in a stepwise manner without involving a 1,5-H migration process. Based on these findings, the authors have proposed a mechanism wherein the
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Published 31 Oct 2024

The scent gland composition of the Mangshan pit viper, Protobothrops mangshanensis

  • Jonas Holste,
  • Paul Weldon,
  • Donald Boyer and
  • Stefan Schulz

Beilstein J. Org. Chem. 2024, 20, 2644–2654, doi:10.3762/bjoc.20.222

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  • article. Numbers refer to the compounds in Table 1. Mass spectra of compounds A–F show characteristic similarities with m/z 141 and ions of the series m/z 41, 55, 69, 83 and m/z 95, 109, 123. The molecular ion increases stepwise by one methylene unit. Structural proposals for compounds A–F. Mass spectrum
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Published 18 Oct 2024

Deciphering the mechanism of γ-cyclodextrin’s hydrophobic cavity hydration: an integrated experimental and theoretical study

  • Stiliyana Pereva,
  • Stefan Dobrev,
  • Tsveta Sarafska,
  • Valya Nikolova,
  • Silvia Angelova,
  • Tony Spassov and
  • Todor Dudev

Beilstein J. Org. Chem. 2024, 20, 2635–2643, doi:10.3762/bjoc.20.221

Graphical Abstract
  • ) that the number of "true" hydrating water molecules in the γ-CD pore is about 7. Effect of the addition of pre-formed water clusters (bulk binding) The stepwise binding of water molecules to the cyclodextrin host appears to be a favorable process. As indicated in our previous studies on α- and β-CDs
  • inclusion into CDs is energetically favorable, characterized predominantly by negative ΔH values. The first few incoming water molecules cluster around the narrow rim due to the higher electron density concentrated at this location. Gradually, a water cluster is formed inside the CD cavity by stepwise
  • [13] and γ-CD dehydration follows a stepwise individual water release, β-CD dehydration is characterized by a one-step release process of water content [14]. A possible explanation of this fact is the different predominance of hydrogen bonds formed between water guests (cluster formation) and between
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Published 17 Oct 2024

Efficient one-step synthesis of diarylacetic acids by electrochemical direct carboxylation of diarylmethanol compounds in DMSO

  • Hisanori Senboku and
  • Mizuki Hayama

Beilstein J. Org. Chem. 2024, 20, 2392–2400, doi:10.3762/bjoc.20.203

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  • proceeds in a stepwise or concerted manner, two-electron reduction of carbonate ion B generates the corresponding diphenylmethyl anion C, which reacts with carbon dioxide to produce a carbon–carbon bond that results in the formation of diphenyl acetate ion D. Electrochemical reduction of carbon dioxide
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Published 20 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

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  • iminoiodinanes: First, the reaction of PhINTs with either cis- or trans-β-methylstyrene (1n) in HFIP afforded aziridine 3n as a mixture of 2.0:1.0 cis/trans (from cis-1n) and 1.0:1.7 cis/trans (from trans-1n) (Scheme 4c). The formation of diastereomeric mixtures suggests that aziridination proceeds in a stepwise
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Published 11 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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  • ]-cycloaddition reaction of fluorinated ketones and aldehydes [49][100] were indicative of the fact that under photochemical conditions, this reaction is likely to be a stepwise process involving the formation of a biradical intermediate. Either (Z)- or (E)-1,2-difluoroethylene easily reacted with
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Published 12 Aug 2024

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

  • Cristina Martini,
  • Muhammad Idham Darussalam Mardjan and
  • Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

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  • /domino reaction, one-pot stepwise synthesis and multicomponent reaction. In the one-pot cascade reaction, the complexity of heterocycles was achieved due to the presence of functional groups formed in the GBB reaction which allow further reactions to occur. In the case of one-pot stepwise synthesis, the
  • optimized conditions allowed them to create a library comprising of 26 polyheterocycles 82 with yields ranging from 71 to 94%. This protocol was scaled up to 10 mmol scale without losing the performance of the GBB multicomponent reaction. Recently, Xiong et al. [61] developed a one-pot stepwise synthesis
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Published 01 Aug 2024

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides

  • Samuel M. G. Dearman,
  • Xiang Li,
  • Yang Li,
  • Kuldip Singh and
  • Alison M. Stuart

Beilstein J. Org. Chem. 2024, 20, 1785–1793, doi:10.3762/bjoc.20.157

Graphical Abstract
  • contains two trifluoromethyl groups in the sidearm which could alter the electronic effects significantly. We therefore decided to prepare a small series of monocyclic trifluoro(aryl)-λ5-iodanes, where the sidearm substituents were changed stepwise from methyl to trifluoromethyl groups, so that we also
  • increased by the stepwise incorporation of the trifluoromethyl groups into the sidearm, but trifluoroiodane 22 was less stable than bicyclic difluoro(aryl)-λ5-iodane 6. Conclusion In summary, we have developed a new strategy using Selectfluor for the convenient preparation and isolation of hypervalent
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Published 29 Jul 2024

Chemo-enzymatic total synthesis: current approaches toward the integration of chemical and enzymatic transformations

  • Ryo Tanifuji and
  • Hiroki Oguri

Beilstein J. Org. Chem. 2024, 20, 1693–1712, doi:10.3762/bjoc.20.151

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  • dearomatization of 33 via enantioselective hydroxylation using molecular oxygen and generates cyclohexadienone 34. As demonstrated by Corey [36] and Nicolaou [37], highly reactive intermediate 34 likely dimerizes non-enzymatically through stepwise reactions involving (1) an initial intermolecular Michael addition
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Published 23 Jul 2024

Divergent role of PIDA and PIFA in the AlX3 (X = Cl, Br) halogenation of 2-naphthol: a mechanistic study

  • Kevin A. Juárez-Ornelas,
  • Manuel Solís-Hernández,
  • Pedro Navarro-Santos,
  • J. Oscar C. Jiménez-Halla and
  • César R. Solorio-Alvarado

Beilstein J. Org. Chem. 2024, 20, 1580–1589, doi:10.3762/bjoc.20.141

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  • reaction proceeds through a stepwise mechanism. Thus, the reaction starts with the coordination of aluminum bromide to an acetate ligand in PIDA to form the PIDA–AlBr3 adduct in a highly exergonic process. Similar to the previous section, the Gibbs free energy at this point was set as 0 kcal/mol for
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Published 15 Jul 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

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  • functional groups on the aromatic ring and adjacent to the benzylic position. Mechanistic investigations suggested an initial electron transfer to generate a radical cation en route to the intermediate benzylic radical, rather than a HAT process, however, the authors did not distinguish between a stepwise
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Published 10 Jul 2024

Synthesis of substituted triazole–pyrazole hybrids using triazenylpyrazole precursors

  • Simone Gräßle,
  • Laura Holzhauer,
  • Nicolai Wippert,
  • Olaf Fuhr,
  • Martin Nieger,
  • Nicole Jung and
  • Stefan Bräse

Beilstein J. Org. Chem. 2024, 20, 1396–1404, doi:10.3762/bjoc.20.121

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  • achieved with a total yield of 37% over all steps, comparable to the total yield of 45% for the stepwise synthesis in the liquid phase. This indicates a material loss due to the non-reactive regioisomer formation in the previous step and a non-quantitative cleavage process. In analogy to the one-pot
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Published 20 Jun 2024
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