Search results

Search for "ethers" in Full Text gives 485 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

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
  • fluoroenynes via Suzuki–Miyaura and Sonogashira cross-coupling reactions using novel multihalogenated fluorovinyl ethers, which are easily prepared from the reaction between phenols and 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane). These reactions make use of the unique structure of multihalogenated
  • fluorovinyl ethers, which contains a reactive bromine atom, to afford a series of fluoroalkenes and fluoroenynes in moderate to high yields. Keywords: fluoroalkenes; fluoroenynes; multihalogenated vinyl ethers; Suzuki–Miyaura cross-coupling reactions; Sonogashira cross-coupling reactions; Introduction
  • development of a dual-reactive fluorine-containing C2-unit, which was prepared from trifluoroethanol in two steps in 63% yield, allowed the convergent synthesis of fluoroalkenes (Scheme 1C) [26]. We recently found multihalogenated vinyl ethers 1 could be obtained by the reaction of phenols with 2-bromo-2
PDF
Album
Supp Info
Full Research Paper
Published 24 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

Graphical Abstract
  • components, carboxylic acids, alcohols, glycerol ethers, amides, and volatile compounds such as phenol, benzaldehyde, or indole were present (Figure 1 and Table 1). While some of these compounds were easily identified, a group of diketopiperazines (DKPs) and a series of unknown putative carboxylic acids (A–F
  • bicolor [8]. These ethers are also found in the scent glands of other reptiles such as lizards [40] and probably act as detergents to increase the solubility of apolar lipids. Amides have been found in Dumeril's Boa and the western diamondback rattlesnake, among others [5][11]. The secretion has also been
PDF
Album
Supp Info
Full Research Paper
Published 18 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

Graphical Abstract
  • > secondary. Functional groups such as silyloxy, amides, ethers, esters, enolizable ketones, and nitriles were found to be compatible with this transformation. Late-stage functionalization of different molecules was demonstrated; for example, the azidation of ibuprofen occurred preferentially at the secondary
PDF
Album
Review
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
PDF
Album
Supp Info
Full Research Paper
Published 26 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
  • ][9][10][11], yielding phenylacetic acids. For example, Troupel et al. successfully performed electrochemical reduction of benzyl ethers and several esters such as acetate, trifluoroacetate, benzoate, and dibenzyl carbonate derived from benzyl alcohols, including 1-phenylethanol compounds, in the
  • mandel acetates [14], respectively. Electrolysis of styrene oxide and related 2-phenylcyclic ethers in the presence of carbon dioxide also induced carboxylation at the benzylic position by reductive cleavage of a C(sp3)–O bond to give the corresponding ω-hydroxy-2-phenylalkanoic acids [15][16]. In
PDF
Album
Supp Info
Full Research Paper
Published 20 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

Graphical Abstract
  • with diketenes (Scheme 1b, path 3) [35] as well as isocyanates with various nucleophilic reagents (Scheme 1b, path 4), such as silyl enol ethers [36], enamines [37], α-acylphosphonium ylides [38] and lithium enolates [39]. Recently, the hydrolysis of α-oxo ketene N,S-acetals was developed to prepare
PDF
Album
Supp Info
Full Research Paper
Published 03 Sep 2024

Natural resorcylic lactones derived from alternariol

  • Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

Graphical Abstract
  • fecal microbiota [107]. Alternariol methyl ethers: Methyl ethers of alternariol have been obtained during chemical structure elucidation and as intermediates in total syntheses of natural products, but some of these have been furthermore isolated as natural products (Figure 5). First to mention is 9-O
PDF
Album
Supp Info
Review
Published 30 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
  • sodium methoxide in an undivided cell, three main products (namely benzophenone dimethyl acetals 133, diphenylmethyl methyl ethers 134 and diphenylmethanes 135) were obtained, the ratio of which was influenced by the electrode materials, the temperature and the amount of sodium methoxide. The range of
PDF
Album
Review
Published 14 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
  • reactions were not described at all. Nevertheless, the radical reactions are the most powerful instrument for the preparation of new molecules with a CHF–CHF fragment. For instance, the radical addition of hypohalites is a suitable high-yielding approach toward polyfluorinated aliphatic ethers and esters
PDF
Album
Review
Published 12 Aug 2024

Syntheses and medicinal chemistry of spiro heterocyclic steroids

  • Laura L. Romero-Hernández,
  • Ana Isabel Ahuja-Casarín,
  • Penélope Merino-Montiel,
  • Sara Montiel-Smith,
  • José Luis Vega-Báez and
  • Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

Graphical Abstract
PDF
Album
Review
Published 24 Jul 2024

Synthetic applications of the Cannizzaro reaction

  • Bhaskar Chatterjee,
  • Dhananjoy Mondal and
  • Smritilekha Bera

Beilstein J. Org. Chem. 2024, 20, 1376–1395, doi:10.3762/bjoc.20.120

Graphical Abstract
  • respective isomers where the geometry of the 1,3-distal dialdehyde 35 was conformationally favorable for the intramolecular hydride attack to take place leading to the formation of the product (Scheme 16). Symmetrical crown ethers having two aldehyde groups 39–42 were functionalized and desymmetrized by
  • [4]arene dialdehydes. Desymmetrization of dialdehydes of symmetrical crown ethers using Ba(OH)2. Synthesis of ottelione A (proposed) via intramolecular Cannizzaro reaction. Intramolecular Cannizzaro reaction for the synthesis of pestalalactone. Synthetic strategy towards nigricanin involving an
PDF
Album
Review
Published 19 Jun 2024

Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C–O bonds in organic transformations

  • Mithu Roy,
  • Bitan Sardar,
  • Itu Mallick and
  • Dipankar Srimani

Beilstein J. Org. Chem. 2024, 20, 1348–1375, doi:10.3762/bjoc.20.119

Graphical Abstract
  • photochemical C–O bond cleavage of ethers in organic transformations has attracted considerable interest. In this context, in 2018, Nicewicz and co-workers [57][58] reported a visible-light-photoredox-catalyzed single-step synthesis of polysubstituted aldehydes using easily accessible olefin substrates (Scheme
  •  21). Styrenes selectively reacted with vinyl ethers in the presence of an acridinium photocatalyst and a diphenyl disulfide HAT catalyst to produce the aldehyde product when exposed to blue LED light. Differently substituted styrenes were examined using this protocol, which produced the aldehyde
  • products in good yield (i.e., 80a–d, 48–80%). Cyclic olefins also performed well under these conditions and generated products with a β-ring moiety (i.e., 80e–g, 60–64%), which would have been challenging to synthesize otherwise. 2-Substituted ethyl vinyl ethers also provided α-branched aldehyde products
PDF
Album
Review
Published 14 Jun 2024

Domino reactions of chromones with activated carbonyl compounds

  • Peter Langer

Beilstein J. Org. Chem. 2024, 20, 1256–1269, doi:10.3762/bjoc.20.108

Graphical Abstract
  • of the substituent located at carbon C3 of the chromone moiety and also on the type of nucleophile employed. Keywords: cyclizations; 1,3-dicarbonyl compounds; domino reactions; heterocycles; regioselectivity; silyl enol ethers; Introduction Domino reactions (also called cascade or tandem reactions
PDF
Album
Review
Published 29 May 2024

Enantioselective synthesis of β-aryl-γ-lactam derivatives via Heck–Matsuda desymmetrization of N-protected 2,5-dihydro-1H-pyrroles

  • Arnaldo G. de Oliveira Jr.,
  • Martí F. Wang,
  • Rafaela C. Carmona,
  • Danilo M. Lustosa,
  • Sergei A. Gorbatov and
  • Carlos R. D. Correia

Beilstein J. Org. Chem. 2024, 20, 940–949, doi:10.3762/bjoc.20.84

Graphical Abstract
  • 4bo (o-phenoxy and o-bromo group, respectively), the er dropped considerably. Finally, a strong electron-withdrawing group in the ortho position such as nitro (4bn) was met with a decrease in yield (66%), but with a higher er. During the development of the scope, the hemiaminal ethers (Heck–Matsuda
  • elimination of methanol favored by the evaporation process. The instability of hemiaminal ethers was previously described in literature [19] during work-up. We then found that careful control of the drying conditions, thus avoiding complete drying of the crude mixture prevents degradation of the Heck products
PDF
Album
Supp Info
Full Research Paper
Published 29 Apr 2024

Three-component N-alkenylation of azoles with alkynes and iodine(III) electrophile: synthesis of multisubstituted N-vinylazoles

  • Jun Kikuchi,
  • Roi Nakajima and
  • Naohiko Yoshikai

Beilstein J. Org. Chem. 2024, 20, 891–897, doi:10.3762/bjoc.20.79

Graphical Abstract
  • difunctionalization of alkynes with various heteroatom and carbon nucleophiles [27][28][29][30][31][32][33][34]. Specifically, intermolecular trans-iodo(III)functionalization of alkynes has been achieved using oxygen nucleophiles such as alcohols [28][32], ethers [33], carboxylic acids [31], phosphate esters [31
PDF
Album
Supp Info
Full Research Paper
Published 22 Apr 2024

(Bio)isosteres of ortho- and meta-substituted benzenes

  • H. Erik Diepers and
  • Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

Graphical Abstract
  • in moderate to good yields, employing 2,7-dimethoxythioxanthone (2,2’-OMeTX) as a triplet sensitizer for BCB excitation (Scheme 3A) [38]. Starting from BCB 24, alkenes including styrene derivatives, enol ethers, and vinyl boronates could be incorporated to give 1,2-BCHs (±)-25a–d. Brown and co
  • cyclopropanation [44] (to (±)-66) of α-hydroxy silyl enol ethers (±)-65 followed by an acid-catalysed pinacol rearrangement to (±)-67. As exemplary derivatizations of 5-oxo-BCH (±)-67, 1,5-BCHs (±)-68, (±)-69 and (±)-70 were accessed by reductive amination, ketone reduction, and Horner–Wadsworth–Emmons olefination
PDF
Album
Review
Published 19 Apr 2024

Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

  • Martyn Jevric,
  • Julian Klepp,
  • Johannes Puschnig,
  • Oscar Lamb,
  • Christopher J. Sumby and
  • Ben W. Greatrex

Beilstein J. Org. Chem. 2024, 20, 823–829, doi:10.3762/bjoc.20.74

Graphical Abstract
  • useful in future studies, they were not examined in this work. To investigate the potential uses for the rearrangement products, a series of reactions on the chloroalkyl ethers 11a and 12a was performed (Scheme 5). The reaction of 11a with allyltrimethylsilane catalysed by aluminium chloride resulted in
PDF
Album
Supp Info
Full Research Paper
Published 16 Apr 2024

Advancements in hydrochlorination of alkenes

  • Daniel S. Müller

Beilstein J. Org. Chem. 2024, 20, 787–814, doi:10.3762/bjoc.20.72

Graphical Abstract
  • , enol ethers, and enamides, proved unproductive in generating the anti-Markovnikov product [90]. The authors attribute this outcome to the high stabilization of the corresponding cations from these substrates, rendering them unresponsive to nucleophilic attack by the chloride anion. Notably, neither the
  • oxidation, whereas in Nicewicz's report, the alkene is oxidized. This modification allows for a significantly larger reaction scope (Scheme 29). Terminal alkenes and several functional groups such as ethers (163), esters (165), ketones (166), nitriles (167), and enones (170) are tolerated. The
PDF
Album
Review
Published 15 Apr 2024

SOMOphilic alkyne vs radical-polar crossover approaches: The full story of the azido-alkynylation of alkenes

  • Julien Borrel and
  • Jerome Waser

Beilstein J. Org. Chem. 2024, 20, 701–713, doi:10.3762/bjoc.20.64

Graphical Abstract
  • reactivity of the C-centered radical with Ph-EBX (2). Aliphatic alkenes, enamides, enol ethers and acrylates were tested in the reaction but did not lead to formation of the desired products (Scheme S1, Supporting Information File 1). In almost all cases >70% of the EBX reagent was left after 16 hours of
PDF
Album
Supp Info
Commentary
Published 03 Apr 2024

Switchable molecular tweezers: design and applications

  • Pablo Msellem,
  • Maksym Dekthiarenko,
  • Nihal Hadj Seyd and
  • Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

Graphical Abstract
  • sites was developed concomitantly to the nitrogen-based systems. In 1999, Boschi and co-workers reported the podand-based switchable tweezers 31 (Figure 17) [66]. This kind of spacer is flexible due to the ethylene glycol chain but can complex alkali cations like crown ethers. Upon complexation, the
PDF
Album
Review
Published 01 Mar 2024

Anion–π catalysis on carbon allotropes

  • M. Ángeles Gutiérrez López,
  • Mei-Ling Tan,
  • Giacomo Renno,
  • Augustina Jozeliūnaitė,
  • J. Jonathan Nué-Martinez,
  • Javier Lopez-Andarias,
  • Naomi Sakai and
  • Stefan Matile

Beilstein J. Org. Chem. 2023, 19, 1881–1894, doi:10.3762/bjoc.19.140

Graphical Abstract
  • catalysis. Moreover, epoxide opening polyether cyclizations are among the most impressive cascade reactions in nature [71][72][73]. Best known is the hypothetical cascade XII in the biosynthesis of brevetoxin B [74]. It affords eleven fused ethers by violating the Eschenmoser–Dunitz–Baldwin guidelines [75
PDF
Album
Review
Published 12 Dec 2023

Recent advancements in iodide/phosphine-mediated photoredox radical reactions

  • Tinglan Liu,
  • Yu Zhou,
  • Junhong Tang and
  • Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

Graphical Abstract
  • and colleagues achieved a significant breakthrough by sequentially unveiling a series of decarboxylative alkylation reactions involving heteroarenes 22, enamides 24, N-arylglycine derivatives 26, and silyl enol ethers 28 [21][22]. Notably, these transformations were accomplished using only a catalytic
PDF
Album
Review
Published 22 Nov 2023

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks

  • Zhang Dongxu

Beilstein J. Org. Chem. 2023, 19, 1741–1754, doi:10.3762/bjoc.19.127

Graphical Abstract
  • group has attracted a significant level of attention, and many trifluoromethylated pyrazoles have been used in medicinal products or in pesticides [66]. The [3 + 2] cycloaddition reactions are considered among the most powerful tools for the synthesis of versatile fluoroalkylated pyrazoles. Enol ethers
PDF
Album
Review
Published 15 Nov 2023

Tying a knot between crown ethers and porphyrins

  • Maksym Matviyishyn and
  • Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

Graphical Abstract
  • the possible future directions. Keywords: crown ethers; porphyrinoids; self-assembly; sensors; supramolecular chemistry; Introduction Many areas of modern supramolecular chemistry, organic, inorganic, materials and coordination chemistry, are based upon macrocyclic compounds of specifically-designed
  • structures and tailored functions [1][2][3]. The design of novel macrocyclic compounds has laid the ground for phenomenal developments constituting supramolecular chemistry as a branch of chemical sciences. These fundamental developments included the discovery of crown ethers by Pedersen [4], followed by the
  • materials science [10]. These two classes of molecules seem particularly remarkable among the endless family of macrocyclic compounds due to their unique features and easy accessibility. The popularity of porphyrins and crown ethers has been so extensive that the whole range of these macrocycles is even
PDF
Album
Perspective
Published 27 Oct 2023

Radical chemistry in polymer science: an overview and recent advances

  • Zixiao Wang,
  • Feichen Cui,
  • Yang Sui and
  • Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

Graphical Abstract
  • advantages are (i) the universality to a wide range of monomers such as (meth)acrylates, (meth)acrylamides, dienes, vinyl ethers/esters, etc.; (ii) tolerance to unprotected functionalities in monomers and the solvent including –OH, –COOH, –SO3H, etc.; (iii) different reaction conditions, including bulk
PDF
Album
Review
Published 18 Oct 2023
Other Beilstein-Institut Open Science Activities