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Search for "allyl" in Full Text gives 502 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Microwave-enhanced additive-free C–H amination of benzoxazoles catalysed by supported copper

  • Andrei Paraschiv,
  • Valentina Maruzzo,
  • Filippo Pettazzi,
  • Stefano Magliocco,
  • Paolo Inaudi,
  • Daria Brambilla,
  • Gloria Berlier,
  • Giancarlo Cravotto and
  • Katia Martina

Beilstein J. Org. Chem. 2025, 21, 1462–1476, doi:10.3762/bjoc.21.108

Graphical Abstract
  • products 2o, 2r and 2s in the range of 61–87%. The protocol demonstrated compatibility with more lipophilic amines, such as 1n, and also tolerated amine 1q containing an allyl substituent. When the reaction was carried out using substituted benzoxazoles (see Scheme 4), their reactivity with piperidine was
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Published 15 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

Graphical Abstract
  • , vinyl, ethynyl or sulphide are sufficient if a superbase such as LIDAKOR or LICKOR is used (Scheme 16) [54][55]. The reaction tends to be remarkably regioselective (in terms of the epoxide opening) and stereoselective, however, it should be treated with caution in case of allyl ethers as they can also
  • polysubstituted oxetanes 64 (Scheme 18) [57]. The mechanism is based on a 1,5-HAT/radical recombination sequence where the H-atom transfer is triggered by an S0 → T1 excitation of the starting allyl ether 63 using an iridium photosensitiser and blue light for irradiation. The method employs mild reaction
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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

Graphical Abstract
  • agents, indicating the feasibility of the protocol (81d,e). The method was further extended to substrates bearing functional groups, such as esters, nitriles, and silanes, all of which were well-tolerated under the optimized conditions (81f–i). Expanding the substrates to include N-allyl-N
  • , α-bromo ketones, and α-bromo nitriles, effectively participated in the reaction (88f–i). Even a more sterically hindered substrate also underwent successful cyclization affording 88j, thus further underscoring the robustness of this transformation. However, attempts using benzyl bromide, allyl
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Published 24 Jun 2025

Synthetic approach to borrelidin fragments: focus on key intermediates

  • Yudhi Dwi Kurniawan,
  • Zetryana Puteri Tachrim,
  • Teni Ernawati,
  • Faris Hermawan,
  • Ima Nurasiyah and
  • Muhammad Alfin Sulmantara

Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91

Graphical Abstract
  • DIBAL-H to aldehyde 110 also resulted in stereochemical inversion (85%, anti/syn >15:1). Subsequent chelation-controlled allylation of aldehyde 110, following Ōmura’s method [27][29], employed allyltrimethylsilane and MgBr2·OEt2, yielding allyl alcohol 111 in 86% yield with exclusive
  • in their laboratory. The strategy primarily involved the reaction of a chiral organometallic reagent 115 with a chiral allyl electrophile 114, as depicted in Scheme 18. The resulting deoxypropionate 113 was obtained with the newly formed stereocenter controlled by the reagent directing group (RDG
  • ) attached to the allyl precursor 114. Iteration of this process required ozonolysis of 113, followed by its conversion to an organometallic intermediate 116, which was then reacted with allyl 114 to yield another deoxypropionate product, 117. The synthesis began with the preparation of the precursor chiral
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Published 12 Jun 2025

Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

  • Betty A. Kustiana,
  • Galuh Widiyarti and
  • Teni Ernawati

Beilstein J. Org. Chem. 2025, 21, 1031–1086, doi:10.3762/bjoc.21.85

Graphical Abstract
  • bond of cyclopropenone to give a cyclic intermediate 316 (Scheme 74A) [125]. On the other hand, Wu and co-workers (2022) developed a Pd-catalyzed selective ring-opening of cyclopropenones and vinyl epoxide 318 to give the corresponding esters 319–321 in good yields via a π–allyl palladium intermediate
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Published 28 May 2025

Biobased carbon dots as photoreductants – an investigation by using triarylsulfonium salts

  • Valentina Benazzi,
  • Arianna Bini,
  • Ilaria Bertuol,
  • Mariangela Novello,
  • Federica Baldi,
  • Matteo Hoch,
  • Alvise Perosa and
  • Stefano Protti

Beilstein J. Org. Chem. 2025, 21, 1024–1030, doi:10.3762/bjoc.21.84

Graphical Abstract
  • material was observed, thus pointing out the key role of CDs in the process. Some additional irradiation was carried out to identify the aryl radical released during the irradiation. Unfortunately, when the reaction was conducted in the presence of both furan and allyl phenyl sulfone [27] no arylation
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Published 26 May 2025

Pd-Catalyzed asymmetric allylic amination with isatin using a P,olefin-type chiral ligand with C–N bond axial chirality

  • Natsume Akimoto,
  • Kaho Takaya,
  • Yoshio Kasashima,
  • Kohei Watanabe,
  • Yasushi Yoshida and
  • Takashi Mino

Beilstein J. Org. Chem. 2025, 21, 1018–1023, doi:10.3762/bjoc.21.83

Graphical Abstract
  • amination of allyl esters using isatin as a nucleophile. In this reaction, bisphosphine-type ligands such as BINAP and SEGPHOS derivatives, as well as P,N-type ligands like oxazoline-type ligands, were utilized as chiral ligands [26]. On the other hand, several groups have recently reported new chiral
  • proceeded when DMF was used (Table 1, entry 11). The reaction in PhCF3 afforded the target product in a good yield with the highest enantioselectivity compared to other solvents (Table 1, entry 12). Furthermore, when (E)-1,3-diphenyl-2-propenyl pivalate (14) was tested as the allyl ester, the desired
  • -catalyzed asymmetric allylic amination of allyl esters with isatin using (aR)-(−)-6 possesses an S-configuration. This stereochemical outcome follows the same reaction mechanism as the Pd-catalyzed asymmetric allylic substitution of allyl esters with indoles using (aR)-(−)-6 [31]. To explore further
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Published 23 May 2025

Recent advances in controllable/divergent synthesis

  • Jilei Cao,
  • Leiyang Bai and
  • Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

Graphical Abstract
  • annulations of strained cyclic allenes with π-allyl palladium complexes and proposed mechanism [22]. Ring expansion of benzosilacyclobutenes with alkynes [23]. Photoinduced regiodivergent and enantioselective cross-coupling [24]. Catalyst-controlled regiodivergent and enantioselective formal hydroamination of
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Published 07 May 2025

Regioselective formal hydrocyanation of allenes: synthesis of β,γ-unsaturated nitriles with α-all-carbon quaternary centers

  • Seeun Lim,
  • Teresa Kim and
  • Yunmi Lee

Beilstein J. Org. Chem. 2025, 21, 800–806, doi:10.3762/bjoc.21.63

Graphical Abstract
  • , ethyl, phenethyl, and allyl groups, also underwent smooth cyanation, resulting in α-quaternary nitriles 3f–i in yields of 85–94%. Furthermore, aryl-substituted allenes 1j–o, incorporating electron-donating or electron-withdrawing substituents such as methyl, fluoro, chloro, bromo, trifluoromethyl, or
  • hydride complex A through the reaction of IPrCuCl with DIBAL-H [35]. Copper hydride species A reacts regioselectively with allene 1 to form the allylcopper intermediate B. Subsequent transmetalation between allyl-Cu B and DIBAL-H generates allylaluminum species C and regenerates IPrCuH (A). The final step
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Published 17 Apr 2025

Recent advances in allylation of chiral secondary alkylcopper species

  • Minjae Kim,
  • Gwanggyun Kim,
  • Doyoon Kim,
  • Jun Hee Lee and
  • Seung Hwan Cho

Beilstein J. Org. Chem. 2025, 21, 639–658, doi:10.3762/bjoc.21.51

Graphical Abstract
  • to the parent allyl group, a variety of 2-substituted electrophiles 31 could be applied. These included those bearing alkyl groups of varying steric demand, halides, and both electron-rich and electron-poor aryl substituents. The olefin coupling partner scope was equally impressive, tolerating
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Published 20 Mar 2025

Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions

  • Xiao-Yang Bi,
  • Xiao-Shuai Yang,
  • Shan-Shan Chen,
  • Jia-Jun Sui,
  • Zhao-Nan Cai,
  • Yong-Ming Chuan and
  • Hong-Bo Qin

Beilstein J. Org. Chem. 2025, 21, 601–606, doi:10.3762/bjoc.21.47

Graphical Abstract
  • synapse growth and inhibits acetylcholinesterase. (±)-Simonsol C (Figure 1) has received considerable attention due to the presence of an aryl- and allyl-containing quaternary carbon center, which is common in natural products such as galanthamine and morphine. To construct the quaternary carbon in
  • construct the aryl and allyl-containing quaternary center, and a simultaneous phenol-initiated oxy-Michael addition to afford the benzofuran unit. This synthesis took 9 steps and achieved an overall yield of 13%. Also in 2024, the Denton group reported another efficient way to access the 6/5/6 benzofuran
  • two allyl groups into the product, thus avoiding the challenges associated with allyl formation reactions. The chosen synthetic route towards (±)-simonsol C is shown in Scheme 3. Starting with magnolol (11), one of the phenol groups was selectively protected by controlling the equivalents of MOMCl and
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Published 17 Mar 2025

Formaldehyde surrogates in multicomponent reactions

  • Cecilia I. Attorresi,
  • Javier A. Ramírez and
  • Bernhard Westermann

Beilstein J. Org. Chem. 2025, 21, 564–595, doi:10.3762/bjoc.21.45

Graphical Abstract
  • product 35b was obtained, confirming that the dihaloalkane compound is the source of the methylene unit (Scheme 28c). Depending on the stability of the leaving carbocation, the selectivity of the R–N cleavage follows the decreasing order for the R groups: H, t-Bu, allyl, benzyl > methyl > primary
  • amine with two methyl groups and a benzyl or allyl group, the cleavage of the N–CH2Ph and N–allyl bond takes place more selective (by 85% and 67%, respectively), instead of the cleavage of an N–Me bond. This explains the high selectivity observed for some examples in Scheme 27. Finally, this methodology
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Published 13 Mar 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

Graphical Abstract
  • of a mixture of 1,2-cis and 1,2-trans glycosides. In this respect ether-type non-participating protecting groups like benzyl (OBn), p-methoxybenzyl (OMBn), and allyl (OAll) are implemented as the temporary protection in the C-2 position in order to obtain 1,2-cis glycoside products. Moreover, the
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Published 17 Feb 2025

Molecular diversity of the reactions of MBH carbonates of isatins and various nucleophiles

  • Zi-Ying Xiao,
  • Jing Sun and
  • Chao-Guo Yan

Beilstein J. Org. Chem. 2025, 21, 286–295, doi:10.3762/bjoc.21.21

Graphical Abstract
  • Figure 1 and Figure 2, it can be found that the C=C bond is located in the unit of the pyrrolidine-2,5-dione, while the scaffold of indolin-2-one is connected via a C–C single bond with the unit of the pyrrolidine-2,5-dione. Therefore, an allyl rearrangement must proceed in the reaction process, which is
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Published 06 Feb 2025

Cu(OTf)2-catalyzed multicomponent reactions

  • Sara Colombo,
  • Camilla Loro,
  • Egle M. Beccalli,
  • Gianluigi Broggini and
  • Marta Papis

Beilstein J. Org. Chem. 2025, 21, 122–145, doi:10.3762/bjoc.21.7

Graphical Abstract
  • directly to the alkene, then reacts with the nucleophile to afford product 7. The regioselective 1,2-difunctionalization of allyl alcohol has been developed as a three-component cascade reaction using arenes and sulfonamides as nucleophiles to achieve arylation/hydroamination processes. The reaction
  • involves a Friedel–Crafts alkylation of the arene followed by hydroamination (Scheme 6) [5]. The mechanism plausibly starts with the in situ formation of triflic acid from Cu(OTf)2 which leads to protonation of the oxygen atom of the alcohol with generation of the activated allyl alcohol. This latter gives
  • the allyl carbenium ion VI through the loss of a molecule of water, then undergoes a Friedel–Crafts alkylation by attack of the aromatic partner. The outcome of the reaction proceeds through a Markovnikov protonation of the allylated arene VII by triflic acid, which generates the carbocation
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Published 14 Jan 2025

Direct trifluoroethylation of carbonyl sulfoxonium ylides using hypervalent iodine compounds

  • Radell Echemendía,
  • Carlee A. Montgomery,
  • Fabio Cuzzucoli,
  • Antonio C. B. Burtoloso and
  • Graham K. Murphy

Beilstein J. Org. Chem. 2024, 20, 3182–3190, doi:10.3762/bjoc.20.263

Graphical Abstract
  • instance, when the bulky tert-butyl ester sulfoxonium ylide was used, the fluoroalkyl product 3f was obtained in 82% yield. A 60% yield was obtained for 3g when the reaction was carried out with the cyclopentyl ester ylide derivative. The allyl sulfoxonium ylide reacted to produce 3h in an excellent 92
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Published 04 Dec 2024

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

  • Lucía Campos-Prieto,
  • Aitor García-Rey,
  • Eddy Sotelo and
  • Ana Mallo-Abreu

Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261

Graphical Abstract
  • ] developed artificial, ‘natural-like’ polyphenols, using the Ugi reaction, since it leads to mixed polyphenol–peptidomimetic structures (Scheme 4). The procedure involved an Ugi reaction using phenolic building blocks protected as allyl ethers, followed by deprotection, acetylation, and high-yielding
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Published 03 Dec 2024

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
  • -workers (Scheme 16) [39]. p-TolIF2 is formed in situ from p-iodotoluene and Selectfluor in a 4.5:1 HF:amine solution, which is obtained by combining Et3N·3HF and pyridine·HF. A range of N-allyl carboxamides 31 were successfully cyclised forming fluoromethyl-2-oxazolines 32 in good yields. The synthesis of
  • [30]. In 2015, Li and co-workers reported the synthesis of chloromethyloxazolines 49 [48] (Scheme 27). Using PhI(OAc)2 as an oxidant and TMSCl as a source of chloride and activator, a range of N-allyl carboxamides 31 were successfully cyclised, forming 5-chloromethyl-2-aryloxazolines 49 in good yields
  • of a range of N-allyl carboxamides 31 with PhI(OAc)2 and TMSBr formed 5-bromomethyl-2-oxazolines 71 in excellent yields. In 2015, Wang and co-workers reported the bromocyclisation of allylamino alcohols 72 to give chiral morpholines 73 (Scheme 38) [56]. Using an amino acid-derived chiral HVI reagent
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Published 28 Nov 2024

Tunable full-color dual-state (solution and solid) emission of push–pull molecules containing the 1-pyrindane moiety

  • Anastasia I. Ershova,
  • Sergey V. Fedoseev,
  • Konstantin V. Lipin,
  • Mikhail Yu. Ievlev,
  • Oleg E. Nasakin and
  • Oleg V. Ershov

Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251

Graphical Abstract
  • configuration of the double bond was confirmed using 1H,1H-NOESY spectroscopy. As shown in Figure 2, a correlation between protons of the allyl moiety and the aryl substituent evidenced their spatial proximity in molecule 1c. The absence of a correlation between allyl and vinyl protons additionally supported
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Published 19 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

Graphical Abstract
  • tert-butylperoxy radical В. Fe(acac)3-catalyzed oxidation of benzyl, allyl and propargyl ethers 78 with TBHP led to the formation of tert-butylperoxyacetals 79 (Scheme 28) [75]. Probably, in the first step TBHP oxidizes Fe(II) to Fe(III) with the formation of tert-butoxy radical A. Then the second
  • reaction of iodine and TBHP forms tert-butoxy radical and tert-butylperoxy radical A. Addition of tert-butylperoxy radical A to diene 220 results in the stable allyl radical B, which reacts with iodine radical to form iodoperoxide C. Elimination
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Published 18 Nov 2024

Multicomponent synthesis of α-branched amines using organozinc reagents generated from alkyl bromides

  • Baptiste Leroux,
  • Alexis Beaufils,
  • Federico Banchini,
  • Olivier Jackowski,
  • Alejandro Perez-Luna,
  • Fabrice Chemla,
  • Marc Presset and
  • Erwan Le Gall

Beilstein J. Org. Chem. 2024, 20, 2834–2839, doi:10.3762/bjoc.20.239

Graphical Abstract
  • ]. In this context, while significant contributions have highlighted the reliable use of diverse organometallic species in the three-component coupling, most examples of sp3-hybridized compounds have remained restricted to allyl [5] or benzyl [5][6] organometallic reagents. Conversely, examples of
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Published 07 Nov 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

Graphical Abstract
  • cation is formed by oxidation of the substrate at the anode. This radical cation is subsequently deprotonated to produce an allyl radical. The allyl radical is further oxidized to form the allyl cation, which is then attacked by the nucleophilic sulfonamide, leading to the formation of the desired C–N
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Published 09 Oct 2024

Phenylseleno trifluoromethoxylation of alkenes

  • Clément Delobel,
  • Armen Panossian,
  • Gilles Hanquet,
  • Frédéric R. Leroux,
  • Fabien Toulgoat and
  • Thierry Billard

Beilstein J. Org. Chem. 2024, 20, 2434–2441, doi:10.3762/bjoc.20.207

Graphical Abstract
  • trifluoromethoxylations of (hetero)aromatics [47][48][49][50][51][52], enol carbonates [53] or silyl enol ethers and allyl silanes [54] have been reported. Most of the methods described have used the trifluoromethoxide anion (CF3O−) [45]. Many sources of the CF3O− anion have been described, but with certain drawbacks
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Published 26 Sep 2024

Asymmetric organocatalytic synthesis of chiral homoallylic amines

  • Nikolay S. Kondratyev and
  • Andrei V. Malkov

Beilstein J. Org. Chem. 2024, 20, 2349–2377, doi:10.3762/bjoc.20.201

Graphical Abstract
  • directly prepared by combining three readily accessible synthons: an amine, an allyl nucleophile, and a carbonyl compound (Scheme 1) [15][16]. A selection of structural motifs accessible via homoallylic amines is shown in Scheme 1. Despite several reviews on homoallylic amine syntheses being published [17
  • two enantiotopic faces of acylimine 2, exposing only one face to the attack by the allyl group. The replacement of one isopropoxy (iPrO) group between allylboronate 1 with BINOL was confirmed by ESI-MS and NMR analysis of the reaction mixture. Interestingly, both (E)- and (Z)-crotyl boronates 6 and 8
  • new methodology used bench-stable allyl-1,3,2-dioxaborinane (27) in the reaction with preformed crude N-aryl-, N-benzyl- and N-allylimines in the presence of 2–8 mol % of the relatively simple 3,3’-Ph2-BINOL catalyst 3 at 50 °C in a microwave reactor at 10 W irradiation for 1 hour to afford amines 26
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Published 16 Sep 2024

Electrochemical allylations in a deep eutectic solvent

  • Sophia Taylor and
  • Scott T. Handy

Beilstein J. Org. Chem. 2024, 20, 2217–2224, doi:10.3762/bjoc.20.189

Graphical Abstract
  • 1:3 molar ratio of tetrabutylammonium bromide and ethylene glycol (TBAB/EG) [28]. Using the reaction of p-anisaldehyde with allyl bromide as a test case, reactions were performed using three sets of different sacrificial electrodes as well as non-sacrificial graphite. As can be seen in Table 1, tin
  • product, although in this case, reduction of the nitro group to an amino group was observed and the resulting 4-aminobenzaldehyde is likely too electron-rich to undergo allylation. The use of other halides was also explored (Table 3). Switching to allyl chloride (Table 3, entry 2) did result in partial
  • conversion, but the reaction was much less efficient than for allyl bromide. More substituted allyl bromides, such as crotyl and prenyl bromide (Table 3, entries 3 and 4) did react, although they afforded only partial conversion when using 2.5 F/mol of current. In terms of regiochemistry, addition at the
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Published 02 Sep 2024
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