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Search for "high yield" in Full Text gives 562 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

5th International Symposium on Synthesis and Catalysis (ISySyCat2023)

  • Anthony J. Burke and
  • Elisabete P. Carreiro

Beilstein J. Org. Chem. 2024, 20, 2704–2707, doi:10.3762/bjoc.20.227

Graphical Abstract
  • novel lipophilic cinchona squaramide organocatalyst. This organocatalyst was evaluated in a benchmark Michael addition of acetylacetone to trans-β-nitrostyrene, yielding the Michael adduct with high yield and enantioselectivity. The hydrophobic chain of the catalyst allowed the organocatalyst to be
  • easily recovered by precipitation using polar solvents. This catalyst proved to be excellent for the preparation of (S)-baclofen on a gram scale, furnishing the main chiral intermediate in high yield and enantioselectivity. Furthermore, the catalyst was recycled over five cycles while maintaining its
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Published 28 Oct 2024

Synthesis of fluoroalkenes and fluoroenynes via cross-coupling reactions using novel multihalogenated vinyl ethers

  • Yukiko Karuo,
  • Keita Hirata,
  • Atsushi Tarui,
  • Kazuyuki Sato,
  • Kentaro Kawai and
  • Masaaki Omote

Beilstein J. Org. Chem. 2024, 20, 2691–2703, doi:10.3762/bjoc.20.226

Graphical Abstract
  • 2a in good yields (Table 1, entries 9–11). Cross-coupling with palladium bis(trifluoroacetate), which is more reactive than palladium diacetate, gave the corresponding product in high yield of 96% (Table 1, entry 12). Without the addition of triphenylphosphine, the reaction proceeded in only 12
  • % yields (Table 3, entries 6–8). The reaction between 1a and 4j, which contains an electron-withdrawing nitro group, afforded 2j in 88% yield (Table 3, entry 9). Although p-hydroxyphenylboronic acid (4k) gave 2k in only 9% yield, m-aminophenylboronic acid (4l) provided 2l in high yield (Table 3, entries 10
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Published 24 Oct 2024

Machine learning-guided strategies for reaction conditions design and optimization

  • Lung-Yi Chen and
  • Yi-Pei Li

Beilstein J. Org. Chem. 2024, 20, 2476–2492, doi:10.3762/bjoc.20.212

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  • to high-yield results from approximately 100,000 experimental conditions using fewer than 100 experiments. Moving from individual synthetic steps to CASP, Nambiar et al. [201] investigated the impact of integrating a global reaction conditions prediction model with local reaction optimization on
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Review
Published 04 Oct 2024

Hypervalent iodine-mediated cyclization of bishomoallylamides to prolinols

  • Smaher E. Butt,
  • Konrad Kepski,
  • Jean-Marc Sotiropoulos and
  • Wesley J. Moran

Beilstein J. Org. Chem. 2024, 20, 2455–2460, doi:10.3762/bjoc.20.209

Graphical Abstract
  • was the five-membered prolinol 7a rather than the initially assigned isomeric seven-membered tetrahydrooxazepine 6 [16]. Subsequently, we set out to understand the O- versus N-chemoselectivity by DFT modelling, and to develop an effective synthetic protocol for the preparation of prolinols 7 in high
  • yield (Scheme 1B). Notably, we are unaware of any reported method to achieve this specific transformation in the literature. Although, Tellitu and co-workers have reported a related preparation of indoline derivatives mediated by bis(trifluoroacetoxy)iodobenzene (PIFA) [17]. Results and Discussion In
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Published 30 Sep 2024

Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles

  • Yutaro Miyashita,
  • Sae Someya,
  • Tomoko Kawasaki-Takasuka,
  • Tomohiro Agou and
  • Takashi Yamazaki

Beilstein J. Org. Chem. 2024, 20, 2421–2433, doi:10.3762/bjoc.20.206

Graphical Abstract
  • the production of the possible olefinic product n-C8H17CH=CH2. Moreover, when the reaction mixture was quenched with D2O, incorporation of deuterium was observed to give 11a-D in a high yield which allowed us to conclude the possible presence of the C-copper species just before quenching. Our result
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Published 25 Sep 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

Graphical Abstract
  • position [19]. Notably, when diphenylmethanol (1a) was used as substrate for electrochemical carboxylation in DMSO, the carboxylation efficiently proceeded to give diphenylacetic acid (2a) in high yield. In this paper, we focus on electrochemical carboxylation of diarylmethanol compounds 1 in DMSO and
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Published 20 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

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  • (DHQ)2PHAL catalyst 138 has been identified as the most efficient that afforded high yield and enantioselectivity with a 10 mol % loading. The diastereoselectivity was 20:1 or better in most cases and was found to be independent of the reaction conditions. The optimised protocol involved stirring 1
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Published 16 Sep 2024

Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides

  • Haifeng Yu,
  • Wanting Zhang,
  • Xuejing Cui,
  • Zida Liu,
  • Xifu Zhang and
  • Xiaobo Zhao

Beilstein J. Org. Chem. 2024, 20, 2225–2233, doi:10.3762/bjoc.20.190

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  • °C, the reaction efficiency significantly decreased (Table 1, entry 13). Alike 2a, the keto isomer of 3a was the dominant isomer, with a keto/enol ratio of 3:1. Then, we tested the effects of different bases on the reaction and found that the strong bases NaOH and KOH gave 3a in high yield (Table 1
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Published 03 Sep 2024

Diastereoselective synthesis of highly substituted cyclohexanones and tetrahydrochromene-4-ones via conjugate addition of curcumins to arylidenemalonates

  • Deepa Nair,
  • Abhishek Tiwari,
  • Banamali Laha and
  • Irishi N. N. Namboothiri

Beilstein J. Org. Chem. 2024, 20, 2016–2023, doi:10.3762/bjoc.20.177

Graphical Abstract
  • base (KOH) and a phase-transfer catalyst (PTC) in a biphasic medium (toluene–H2O) at room temperature, leading to highly functionalized cyclohexanones and tetrahydrochromenones as major and minor products, respectively, in moderate to high yield and excellent diastereoselectivity. Results and
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Published 15 Aug 2024

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

  • Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

Graphical Abstract
  • -tetraethylammonium perchlorate solution under constant potential in a divided cell equipped with platinum gauze anode and nickel cathode. Such a transformation constituted a straightforward route to the corresponding fused s-triazolo perchlorates 46 in moderate to high yield. Coulometric analysis established that
  • aldehyde-derived N,N-dialkylhydrazones 123 under constant current with two carbon electrodes. Aromatic and aliphatic sodium sulfinates 124 were employed as sources of sulfinate radicals under electrolyte-free reaction conditions. The targeted product was obtained in high yield regardless of the electronic
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Published 14 Aug 2024

Development of a flow photochemical process for a π-Lewis acidic metal-catalyzed cyclization/radical addition sequence: in situ-generated 2-benzopyrylium as photoredox catalyst and reactive intermediate

  • Masahiro Terada,
  • Zen Iwasaki,
  • Ryohei Yazaki,
  • Shigenobu Umemiya and
  • Jun Kikuchi

Beilstein J. Org. Chem. 2024, 20, 1973–1980, doi:10.3762/bjoc.20.173

Graphical Abstract
  • , the reaction of substrate 1c having a methyl group as a weak electron-donating group at the para-position afforded product 3c in high yield (Table 2, entry 3: 76%). In addition, the reaction of 1d having a bromo group resulted in a moderate yield, but with a significant improvement compared with the
  • batch reaction (Table 2, entry 4: 57% vs 10%). The reaction of 1e substituted with a strong electron-withdrawing trifluoromethyl group afforded the product 3e in high yield (Table 2, entry 5: 77%), again confirming the high efficiency of the flow reaction system (batch: 54%). Next, the effects of the
  • of the ortho-substituent (Table 2, entry 10 vs entries 3 and 7). When a fluoro group was introduced to the tethering phenyl backbone, a high yield was obtained regardless of whether it was introduced at the 6- or 7-position (Table 2, entries 11 and 12). Next, the effects of a carbonyl substituent
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Published 13 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

Graphical Abstract
  • -difluoroethylene and the disappearance of vinyl protons resonances in the 1H NMR spectra [78]. Addition to the C=C bond Halogen addition: 1,2-Difluoroethylene was reported to react with chlorine [46][79] and bromine [51] under irradiation, yielding 1,2-difluoro-1,2-dihaloethanes in moderate to high yield (Scheme 9
  • (trifluoromethyl)amine easily reacted with (Z)-1,2-difluoroethylene to form the addition product in high yield (Scheme 11) [89]. However, the stereochemistry of this reaction has not been reported. A similar reaction of (Z)-1,2-difluoroethylene with N-chloroimidobis(sulfonyl fluoride) (Scheme 12) [90] was shown to
  • be stereounspecific, although the addition product was reported to form in high yield. In the same publication [90], it was mentioned that (FSO2)2NH did not form an addition product in the reaction with (Z)-1,2-difluoroethylene, although the reaction of (FSO2)2NH with other olefins, including
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Published 12 Aug 2024

Negishi-coupling-enabled synthesis of α-heteroaryl-α-amino acid building blocks for DNA-encoded chemical library applications

  • Matteo Gasparetto,
  • Balázs Fődi and
  • Gellért Sipos

Beilstein J. Org. Chem. 2024, 20, 1922–1932, doi:10.3762/bjoc.20.168

Graphical Abstract
  • acetate 2i in high yield. A similar result was obtained for the furanyl derivative 2j. Pyrazoles were the only substrate class which clearly benefited from light irradiation (2k–o), displaying not just a shorter reaction time but also higher yields. Even unprotected pyrazoles (2k, 2m, 2n) performed well
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Published 08 Aug 2024

Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA

  • Ze-Nan Hu,
  • Yan-Hui Wang,
  • Jia-Bing Wu,
  • Ze Chen,
  • Dou Hong and
  • Chi Zhang

Beilstein J. Org. Chem. 2024, 20, 1914–1921, doi:10.3762/bjoc.20.167

Graphical Abstract
  • , respectively, the substrates could be successfully converted to the products 3b–d and 2f in 52–87% yield with this method. In addition, a good or high yield of 3-methylisoquinolinones 3e–k, with different substituents on the phenyl ring, was also obtained. It is worth noting that when an electron-withdrawing
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Published 07 Aug 2024

Electrochemical radical cation aza-Wacker cyclizations

  • Sota Adachi and
  • Yohei Okada

Beilstein J. Org. Chem. 2024, 20, 1900–1905, doi:10.3762/bjoc.20.165

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  • ), with platinum (Pt) as a cathode. To our delight, a constant-current condition at 1 mA was productive, and the desired five-membered pyrrolidine 2 was obtained in high yield (Table 1, entry 2). During the screening of conditions, the addition of acetonitrile (CH3CN) was found to be effective, probably
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Published 05 Aug 2024

Access to 2-oxoazetidine-3-carboxylic acid derivatives via thermal microwave-assisted Wolff rearrangement of 3-diazotetramic acids in the presence of nucleophiles

  • Ivan Lyutin,
  • Vasilisa Krivovicheva,
  • Grigory Kantin and
  • Dmitry Dar’in

Beilstein J. Org. Chem. 2024, 20, 1894–1899, doi:10.3762/bjoc.20.164

Graphical Abstract
  • derivative 3a could be obtained in high yield (83%) after simple chromatographic separation of the reaction mixture (Scheme 2). When the synthesis was carried out using conventional heating in 1,2-dichlorobenzene (200 °C, 1 h), product 3a was obtained in slightly lower yield (75%), so further experiments
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Published 05 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

Graphical Abstract
  • derivatization, allowed the obtainment of 18 in high yield under relatively mild conditions, and was extended to the synthesis of 23 analogues, all in high yields (>86%). The catalyst could be recovered from the reaction medium by precipitation and reused up to five times without loss in activity. In 2020, Tyagi
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Published 01 Aug 2024

Chiral bifunctional sulfide-catalyzed enantioselective bromolactonizations of α- and β-substituted 5-hexenoic acids

  • Sao Sumida,
  • Ken Okuno,
  • Taiki Mori,
  • Yasuaki Furuya and
  • Seiji Shirakawa

Beilstein J. Org. Chem. 2024, 20, 1794–1799, doi:10.3762/bjoc.20.158

Graphical Abstract
  • substrate was also examined to give a dihydroisocoumarin product 3o in high yield with moderate enantioselectivity. The absolute stereochemistry of the bromolactonization product 3o was confirmed by comparison with reported data [24]. The transformations of the optically active bromolactonization product 3a
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Published 30 Jul 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
  • efficient separation from the excess Selectfluor and its byproduct. Reducing the amount of Selectfluor to 2.5 equivalents and the reaction time to 24 hours (Table 2, entry 2) resulted in a similar high yield of difluoroiodane 6. The reaction also proceeded well at either room temperature for 24 hours (Table
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Published 29 Jul 2024

Oxidation of benzylic alcohols to carbonyls using N-heterocyclic stabilized λ3-iodanes

  • Thomas J. Kuczmera,
  • Pim Puylaert and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 1677–1683, doi:10.3762/bjoc.20.149

Graphical Abstract
  • isolated in a high yield of 84% with reisolation of the 5-(2-iodophenyl)-1H-tetrazole (6) in 90% yield. Other para-halogenated benzaldehydes 4b–f were isolated in good yields of up to 88%. ortho-Substitution led to a lower yield of the iodinated product 4g (43%) compared to the para-iodinated analogues 4d
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Published 19 Jul 2024

Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty

  • Weimao Zhong and
  • Vinayak Agarwal

Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146

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  • 8.0 and 55 °C, respectively. The biocatalytic utility of the enzyme was also evaluated; it was used for neoagarooligosaccharide production in high yield [80]. Five additional GH-16 agarases AgaA3 produced in B. subtilis, ID2563 produced in E. coli, N3-1 produced in Pichia pastoris, AG1 produced in E
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Published 17 Jul 2024

New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)

  • Fátima C. Teixeira,
  • António P. S. Teixeira and
  • C. M. Rangel

Beilstein J. Org. Chem. 2024, 20, 1623–1634, doi:10.3762/bjoc.20.145

Graphical Abstract
  • )methylene]bis(phosphonate) (13) [56] was successfully achieved, with high yield, by the reaction of diethyl phosphonate with 4-hydroxybenzaldehyde (12) in the presence of sodium metal. A reaction to obtain the corresponding amino derivative 14 [57] was carried out starting from 4-nitrobenzaldehyde (15
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Published 17 Jul 2024

Electrocatalytic hydrogenation of cyanoarenes, nitroarenes, quinolines, and pyridines under mild conditions with a proton-exchange membrane reactor

  • Koichi Mitsudo,
  • Atsushi Osaki,
  • Haruka Inoue,
  • Eisuke Sato,
  • Naoki Shida,
  • Mahito Atobe and
  • Seiji Suga

Beilstein J. Org. Chem. 2024, 20, 1560–1571, doi:10.3762/bjoc.20.139

Graphical Abstract
  • more π-extended aniline was easily obtained in a high yield. Reduction of quinolines to tetrahydroquinolines The electrochemical reduction of quinolines was performed using a PEM reactor. First, several different cathode catalyst were examined for the reduction of quinoline (6a) (Table 5). Because 4.0
  • was reused eight times, and 7a was obtained in high yield in each run. The addition of pyridinium p-toluenesulfonate (PPTS) was also efficient, and MEA was repeatedly used to afford 7a in high yield (Figure 4). After further tunings, we found that the charge for electro-reduction of 6a could be
  • selectively afforded the desired products. A substrate with a methoxy group at the 8-position (6o) afforded the desired product 7o in high yield. However, 6p and 6q with a methoxy group at the 6- and 3-position gave only a small amount of the target product, and 6r with a methoxy group at the 4-position gave
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Published 11 Jul 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

Graphical Abstract
  • found to be suitable coupling partners. Aryl chloride 1a reacted with tert-butyl acrylate (2b) without any difficulty, providing 3ab in a high yield. Methacrylamide (2c) and acrylonitrile (2d) were transformed into the corresponding products in high yields, but with slightly lower Faradaic efficiency
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Published 10 Jun 2024

Synthesis of indano[60]fullerene thioketone and its application in organic solar cells

  • Yong-Chang Zhai,
  • Shimon Oiwa,
  • Shinobu Aoyagi,
  • Shohei Ohno,
  • Tsubasa Mikie,
  • Jun-Zhuo Wang,
  • Hirofumi Amada,
  • Koki Yamanaka,
  • Kazuhira Miwa,
  • Naoyuki Imai,
  • Takeshi Igarashi,
  • Itaru Osaka and
  • Yutaka Matsuo

Beilstein J. Org. Chem. 2024, 20, 1270–1277, doi:10.3762/bjoc.20.109

Graphical Abstract
  • converted to indano[60]fullerene thioketone (FIDS) in high yield by using Lawesson's reagent. Three compounds with different substituents in para position were successfully converted to the corresponding thioketones, showing that the reaction tolerates compounds with electron-donating and electron
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Published 31 May 2024
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