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Search for "organocatalysis" in Full Text gives 172 result(s) in Beilstein Journal of Organic Chemistry.

A laterally-fused N-heterocyclic carbene framework from polysubstituted aminoimidazo[5,1-b]oxazol-6-ium salts

  • Andrew D. Gillie,
  • Matthew G. Wakeling,
  • Bethan L. Greene,
  • Louise Male and
  • Paul W. Davies

Beilstein J. Org. Chem. 2024, 20, 621–627, doi:10.3762/bjoc.20.54

Graphical Abstract
  • ; imidazolium; NHC; Introduction Imidazolium-derived nucleophilic heterocyclic carbenes (NHCs) have had a sustained impact across the fields of organometallic and main group chemistry, transition-metal catalysis, materials synthesis and organocatalysis [1]. Laterally annellated polycyclic NHCs offer a useful
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Published 18 Mar 2024

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

  • Periklis X. Kolagkis,
  • Eirini M. Galathri and
  • Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

Graphical Abstract
  • development of greener synthetic technologies, like photocatalysis, organocatalysis, the use of nanocatalysts, microwave irradiation, ball milling, continuous flow, and many more. Thus, in this review, we summarize the medicinal properties of BIMs and the developed BIM synthetic protocols, utilizing the
  • of green chemistry. Organocatalysis is the acceleration of chemical reactions with the use of small organic compounds, which do not contain any amounts of enzyme or inorganic elements [37][38][39]. The benefits of solid acid catalysis render them as an appealing choice, compared to their liquid
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Review
Published 22 Feb 2024

Catalytic multi-step domino and one-pot reactions

  • Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2024, 20, 254–256, doi:10.3762/bjoc.20.25

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  • ; multi-step reactions; multicomponent reactions; one-pot synthesis; organocatalysis; tandem reactions; transition-metal-catalysis; The synthesis of pharmaceutical ingredients, natural products, agrochemicals, ligand systems, and building blocks for materials science has reached a high level of
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Editorial
Published 08 Feb 2024

Chiral phosphoric acid-catalyzed transfer hydrogenation of 3,3-difluoro-3H-indoles

  • Yumei Wang,
  • Guangzhu Wang,
  • Yanping Zhu and
  • Kaiwu Dong

Beilstein J. Org. Chem. 2024, 20, 205–211, doi:10.3762/bjoc.20.20

Graphical Abstract
  • excellent yield and enantioselectivity. Keywords: asymmetric organocatalysis; chiral Brønsted acid; 3,3-difluoroindoline; Hantzsch ester; transfer hydrogenation; Introduction The introduction of fluoro atoms into organic molecules can alter their lipophilicity, solubility, metabolic stability, and
  • organocatalysis using chiral phosphoric acids has also been studied (Scheme 1b) [26][27][28]. In 2010, Magnus Rueping and his co-workers developped an enantioselective Brønsted acid-catalyzed transfer hydrogenation of 3H-indoles [29]. In 2020, Song and Yu successfully applied a new chiral Brønsted acid
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Published 01 Feb 2024

Using the phospha-Michael reaction for making phosphonium phenolate zwitterions

  • Matthias R. Steiner,
  • Max Schmallegger,
  • Larissa Donner,
  • Johann A. Hlina,
  • Christoph Marschner,
  • Judith Baumgartner and
  • Christian Slugovc

Beilstein J. Org. Chem. 2024, 20, 41–51, doi:10.3762/bjoc.20.6

Graphical Abstract
  • Matthias R. Steiner Max Schmallegger Larissa Donner Johann A. Hlina Christoph Marschner Judith Baumgartner Christian Slugovc Institute for Chemistry and Technology of Materials, Graz University of Technology, Stremayrgasse 9, 8010 Graz, Austria Christian Doppler Laboratory for Organocatalysis in
  • reactive in chloroform solution, while in methanol the corresponding phosphonium phenolate is formed. Keywords: Lewis-base catalysis; Michael acceptor reactivity; phospha-Michael reaction; phosphonium phenolate zwitterion; Introduction Organocatalysis has emerged in recent years as a valuable and
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Published 10 Jan 2024

Aldiminium and 1,2,3-triazolium dithiocarboxylate zwitterions derived from cyclic (alkyl)(amino) and mesoionic carbenes

  • Nedra Touj,
  • François Mazars,
  • Guillermo Zaragoza and
  • Lionel Delaude

Beilstein J. Org. Chem. 2023, 19, 1947–1956, doi:10.3762/bjoc.19.145

Graphical Abstract
  • weaker basicity and greater modularity, the related 1,2,4-triazol-5-ylidene derivatives D have been mainly employed in organocatalysis [6]. Besides these four types of N-heterocyclic carbenes (NHCs), other families of cyclic compounds have been actively pursued to further expand the diversity of singlet
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Published 20 Dec 2023

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

  • Gyula Dargó,
  • Dóra Erdélyi,
  • Balázs Molnár,
  • Péter Kisszékelyi,
  • Zsófia Garádi and
  • József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

Graphical Abstract
  • , acetonitrile, with 91–100% efficiency, and the catalyst was reused in five reaction cycles without the loss of activity and selectivity. Keywords: baclofen; catalyst recovery; lipophilic cinchona squaramide; organocatalysis; stereoselective catalysis; Introduction In today’s chemical industry, catalytic
  • processes are of paramount importance. In particular, the application of asymmetric organocatalysts is receiving increased attention [1][2][3][4]. This is illustrated by the fact that in 2021 the Nobel Prize in Chemistry was awarded for the discovery of asymmetric organocatalysis [5]. The use of
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Published 24 Nov 2023

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

  • Fatemeh Doraghi,
  • Seyedeh Pegah Aledavoud,
  • Mehdi Ghanbarlou,
  • Bagher Larijani and
  • Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

Graphical Abstract
  • synthesis of chiral sulfides up to 97% ee was achieved in this method. A wide range of cyclic alkenes 138 and acyclic alkenes 52 and 9 were smoothly tolerated in this organocatalysis strategy. According to the proposed mechanism, initially, the organocatalyst activated the electrophilic sulfur species to
  • reduction of II by silane. On the other hand, most of II were converted to intermediate III, which underwent hydride reduction to render product 140 (Scheme 61). Another organocatalysis system was disclosed by Liu and co-workers for sulfenylation of α-fluoro-β-ketoamides 143 and azlactones 145 (Scheme 62
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Published 27 Sep 2023

Acetaldehyde in the Enders triple cascade reaction via acetaldehyde dimethyl acetal

  • Alessandro Brusa,
  • Debora Iapadre,
  • Maria Edith Casacchia,
  • Alessio Carioscia,
  • Giuliana Giorgianni,
  • Giandomenico Magagnano,
  • Fabio Pesciaioli and
  • Armando Carlone

Beilstein J. Org. Chem. 2023, 19, 1243–1250, doi:10.3762/bjoc.19.92

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  • enantioselectivity. Keywords: acetaldehyde; acetaldehyde dimethyl acetal; cascade reaction; multicomponent reaction; organocatalysis; Introduction Multicomponent reactions (MCRs) are chemical processes that involve three or more compounds, in which the product contains all the atoms of the reagents, except for
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Published 24 Aug 2023

Exploring the role of halogen bonding in iodonium ylides: insights into unexpected reactivity and reaction control

  • Carlee A. Montgomery and
  • Graham K. Murphy

Beilstein J. Org. Chem. 2023, 19, 1171–1190, doi:10.3762/bjoc.19.86

Graphical Abstract
  • ][78][79][80][81][82]. Organocatalysis is also a common point of intersection for halogen- and hydrogen bonding, and this has been thoroughly explored using monovalent iodine catalysts [83][84][85]. 1.3 Halogen bonding in hypervalent iodine complexes Similar to monovalent iodine compounds, a diverse
  • compounds have also played an active role in halogen bond-based organocatalysis [91][92][93][94][95][96][97]. 2 Halogen bonding in iodonium ylides 2.1 Quantification of σ-holes in iodonium ylides Until recently, there were no quantitative evaluations of σ-holes in iodonium ylides [98][99], even though
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Published 07 Aug 2023
Graphical Abstract
  • stereoselectivity is also explained. Keywords: asymmetric; aza-Friedel–Crafts reaction; H-bonding; organocatalysis; stereoselectivity; Introduction The ease of a chemical transformation depends on the thermodynamic instability of a chemical bond owing to its fast cleavage under mild reaction conditions. A C–H
  • the tremendous progress in organic chemistry over the last few decades, metal catalysis has been increasingly and successfully replaced by organocatalysis, i.e., accelerating the rate of chemical transformations by using small organic molecules as catalysts. Although being discovered more than 100
  • years ago, the concept became increasingly accepted and popular only by the last decade of the last century [2][3]. Nowadays, organocatalysis is especially applied to asymmetric synthesis and a huge number of organocatalysts has been introduced in last three decades for the asymmetric synthesis of
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Published 28 Jun 2023

Total synthesis: an enabling science

  • Bastien Nay

Beilstein J. Org. Chem. 2023, 19, 474–476, doi:10.3762/bjoc.19.36

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  • synthetic methodology developments and to natural product isolation or biosynthesis. Thus, thematic issues dealing with total synthesis in the Beilstein Journal of Organic Chemistry have naturally been published in these fields, such as "Transition-metal and organocatalysis in natural product synthesis
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Editorial
Published 19 Apr 2023

NaI/PPh3-catalyzed visible-light-mediated decarboxylative radical cascade cyclization of N-arylacrylamides for the efficient synthesis of quaternary oxindoles

  • Dan Liu,
  • Yue Zhao and
  • Frederic W. Patureau

Beilstein J. Org. Chem. 2023, 19, 57–65, doi:10.3762/bjoc.19.5

Graphical Abstract
  • advantage of circumventing the need for external redox additives and/or noble metals, using readily available and cost-effective NaI and PPh3 under mild reaction conditions. In a broader context, phosphine organocatalysis is probably still underappreciated in organic synthesis, and could lead to important
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Published 16 Jan 2023

Two-step continuous-flow synthesis of 6-membered cyclic iodonium salts via anodic oxidation

  • Julian Spils,
  • Thomas Wirth and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2023, 19, 27–32, doi:10.3762/bjoc.19.2

Graphical Abstract
  • -established reagents for synthetic chemists. They are portrayed as an alternative to otherwise hazardous transition metals. This is due to their great reactivity in electrophilic group transfers [1][2][3][4], photo- or organocatalysis [5][6][7][8][9][10][11][12][13][14][15], and their utility as building
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Published 03 Jan 2023

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

  • Elena R. Lopat’eva,
  • Igor B. Krylov,
  • Dmitry A. Lapshin and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

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  • Elena R. Lopat'eva Igor B. Krylov Dmitry A. Lapshin Alexander O. Terent'ev N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow, 119991, Russia 10.3762/bjoc.18.179 Abstract Organocatalysis is widely recognized as a key synthetic methodology in
  • organic chemistry. It allows chemists to avoid the use of precious and (or) toxic metals by taking advantage of the catalytic activity of small and synthetically available molecules. Today, the term organocatalysis is mainly associated with redox-neutral asymmetric catalysis of C–C bond-forming processes
  • oxidative, catalyzed by redox-active organic molecules in the ground state (without light excitation). Unfortunately, many of such processes are not associated in the literature with the organocatalysis field and thus many achievements are not fully consolidated and systematized. The present article is
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Published 09 Dec 2022

Design, synthesis, and evaluation of chiral thiophosphorus acids as organocatalysts

  • Karen R. Winters and
  • Jean-Luc Montchamp

Beilstein J. Org. Chem. 2022, 18, 1471–1478, doi:10.3762/bjoc.18.154

Graphical Abstract
  • asymmetric organocatalysis. In order to eliminate the need for C2-symmetry in common CPAs, various scaffolds containing C1-symmetrical thiophosphorus acids were chosen. These new compounds were synthesized and evaluated in the asymmetric transfer hydrogenation of 2-phenylquinoline. Although the efficacy of
  • the thiophosphorus acids was disappointing for this reaction, the work should be useful for developing structural design elements. Keywords: asymmetric; heterocycles; organocatalysis; phosphorus; synthesis; Introduction The importance of asymmetric organocatalysis was demonstrated by the 2021 Nobel
  • SPINOL [4][5] (Figure 1). The great success of these CPAs in asymmetric organocatalysis, is demonstrated by the publication of thousands of articles and reviews [6][7][8][9][10][11][12][13][14][15][16][17]. In all cases the C2-symmetry is required because of the prototropic tautomeric equilibrium in the
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Published 17 Oct 2022

First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell

  • Daniele Rocco,
  • Ana A. Folgueiras-Amador,
  • Richard C. D. Brown and
  • Marta Feroci

Beilstein J. Org. Chem. 2022, 18, 979–990, doi:10.3762/bjoc.18.98

Graphical Abstract
  • at the cathode is usually H2 evolution [29]. The use of divided cells is less common in organic electrosynthesis, mainly due to complications inherent with membranes. Useful cathodic processes are less exploited in organic electrochemistry. In the context of NHC organocatalysis in flow
  • ). Therefore, the 32% chemical yield (with respect to starting IL) is comparable with the yield of the batch process. Electrogenerated NHC organocatalysis. Dimerization of trans-cinnamaldehyde: synthesis of 4-phenyl-5-styryldihydrofuran-2(3H)-one Having demonstrated that NHCs could be generated and accumulated
  • anolyte, a lower amount of both diastereoisomers was observed (Table 2, entries 5 and 6). Thus the best yield (79%, 67:33 cis/trans ratio) was obtained using a charge of 2.0 F and a solution of MeCN–MeOH (9.5:0.5)/Et4NBF4 (0.1 M) as anolyte (Table 2, entry 3). Electrogenerated NHC organocatalysis
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Published 05 Aug 2022

Continuous flow synthesis of azobenzenes via Baeyer–Mills reaction

  • Jan H. Griwatz,
  • Anne Kunz and
  • Hermann A. Wegner

Beilstein J. Org. Chem. 2022, 18, 781–787, doi:10.3762/bjoc.18.78

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  • . Keywords: azobenzenes; Baeyer–Mills reaction; continuous flow; molecular switches; solar fuel; Introduction Although the red-colored azobenzenes (AB) have been known for years as dyes, their applications nowadays span from energy and information storage [1][2][3][4][5], organocatalysis [6], photobiology
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Published 30 Jun 2022

BINOL as a chiral element in mechanically interlocked molecules

  • Matthias Krajnc and
  • Jochen Niemeyer

Beilstein J. Org. Chem. 2022, 18, 508–523, doi:10.3762/bjoc.18.53

Graphical Abstract
  • limited to) metal- and organocatalysis [30] and stereoselective chemosensing [31][32]. By introduction of an axially chiral BINOL unit into a MIM, it is possible to combine the unique applicability of the chiral BINOL unit with the special possibilities offered by interlocked molecules. In this minireview
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Published 06 May 2022

A resorcin[4]arene hexameric capsule as a supramolecular catalyst in elimination and isomerization reactions

  • Tommaso Lorenzetto,
  • Fabrizio Fabris and
  • Alessandro Scarso

Beilstein J. Org. Chem. 2022, 18, 337–349, doi:10.3762/bjoc.18.38

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  • compared to many other strong Brønsted or Lewis acids. Keywords: cationic intermediates; encapsulation; organocatalysis; resorcin[4]arene hexamer; supramolecular catalysis; Introduction In enzymatic catalysis, the substrate is selected matching the size, shape and specific functional groups present in
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Published 28 Mar 2022

New advances in asymmetric organocatalysis

  • Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 240–242, doi:10.3762/bjoc.18.28

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  • Radovan Sebesta Department of Organic Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, Ilkovičova 6, 842 15 Bratislava, Slovakia 10.3762/bjoc.18.28 Keywords: asymmetric organocatalysis; covalent activation; noncovalent activation; Asymmetric catalysis is
  • [12]. The recent culmination of the rapid advent of organocatalysis was the Nobel prize in 2021, which was awarded to Benjamin List and David MacMillan for their pioneering discoveries. Organocatalysis outgrew its initial inspiration by enzymatic catalysis, but the analogy with nature can be seen
  • repertoire of chemical transformations that are amenable to organocatalysis [14]. Within the realm of covalent activation, chiral carbenes and phosphines are diverse and structurally rich groups of catalysts. The synthetic scope was greatly expanded by noncovalent activation via a range of proton-mediated
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Published 28 Feb 2022

Asymmetric organocatalytic Michael addition of cyclopentane-1,2-dione to alkylidene oxindole

  • Estelle Silm,
  • Ivar Järving and
  • Tõnis Kanger

Beilstein J. Org. Chem. 2022, 18, 167–173, doi:10.3762/bjoc.18.18

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  • presence of a multifunctional squaramide catalyst. Michael adducts were obtained in high enantioselectivities and in moderate diastereoselectivities. Keywords: cyclopentane-1,2-dione; enantioselective catalysis; Michael addition; organocatalysis; squaramide; Introduction Diketones are generally very
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Published 03 Feb 2022

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet–Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

  • Marco Keller,
  • Karl Sauvageot-Witzku,
  • Franz Geisslinger,
  • Nicole Urban,
  • Michael Schaefer,
  • Karin Bartel and
  • Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2716–2725, doi:10.3762/bjoc.17.183

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  • arylacetaldimines of phenylethylamines [2] (Figure 1). Especially the Pictet–Spengler reaction has attracted considerable interest in chemistry and drug development in recent years, and modern methods like enantioselective approaches, organocatalysis, and enzymatic methods have been introduced by numerous groups [3
  • enantioselective organocatalysis based on Jacobsen’s pioneering work [56]. Since we had recently identified substituted 1-benzyltetrahydroisoquinolines as truncated analogues of bioactive bisbenzylisoquinoline alkaloids (SG-005 and SG-094) as TPC2 blockers with antiproliferative activity, we tested our alkaloids
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Published 05 Nov 2021

Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions

  • Akhil K. Dubey and
  • Raghunath Chowdhury

Beilstein J. Org. Chem. 2021, 17, 2642–2649, doi:10.3762/bjoc.17.177

Graphical Abstract
  • experiments reveal that the presence of a β-silyl group in the enones is crucial for high reactivity under the optimized reaction conditions. Keywords: β-silyl α,β-unsaturated carbonyl compounds; β-silyl nitroalkanes; chiral organosilanes; organocatalysis; solvent-free synthesis; Introduction
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Published 27 Oct 2021

N-Sulfinylpyrrolidine-containing ureas and thioureas as bifunctional organocatalysts

  • Viera Poláčková,
  • Dominika Krištofíková,
  • Boglárka Némethová,
  • Renata Górová,
  • Mária Mečiarová and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2021, 17, 2629–2641, doi:10.3762/bjoc.17.176

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  • aldehydes and hydrogen-bond activation of nitroalkenes. Keywords: asymmetric organocatalysis; hydrogen bond; Michael addition; pyrrolidine; thiourea; urea; Introduction Asymmetric organocatalysis became one of the strategic ways for the efficient synthesis of chiral compounds [1]. Bifunctional catalysis
  • has proven to be a successful concept in asymmetric organocatalysis [2][3][4][5][6][7][8]. An amine unit with a hydrogen-bond donating skeleton is highly efficient from among various possible combinations of catalytic moieties within an organocatalyst. This idea has been inspired by proline catalysis
  • organocatalysis can benefit and accommodate many sustainability techniques [29]. Mechanochemistry can increase the sustainability profile of a chemical process by reducing potentially harmful organic solvents and bring other benefits such as substantially shortened reaction times. A handful of asymmetric
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Published 25 Oct 2021
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