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Search for "molecular complexity" in Full Text gives 47 result(s) in Beilstein Journal of Organic Chemistry.

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

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  • the MCR product is possible thus increasing the versatility of these reactions in terms of structural diversity and molecular complexity. In this context, a wide variety of heterocycles and macrocycles as important biological scaffolds have been synthesized [6]. One of the most important components
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Published 13 Mar 2025

Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light

  • Francesco Gambuti,
  • Jacopo Pizzorno,
  • Chiara Lambruschini,
  • Renata Riva and
  • Lisa Moni

Beilstein J. Org. Chem. 2024, 20, 2722–2731, doi:10.3762/bjoc.20.230

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  • ]. Among the common compound collections for drug discovery, the introduction of spirocyclic elements presents an attractive strategy for increasing molecular complexity without increasing molecular weight, and at the same time, for introducing structural novelty for patentability [3]. However, the
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Published 29 Oct 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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  • -trifluoromethylamine derivatives of high molecular complexity (Scheme 28). The process involves a highly enantioselective reaction of the isatin-derived Morita–Baylis–Hillman carbonate 137 with a novel α-CF3-substituted imine 136, derived from inexpensive benzothiophene-2,3-dione. A C2-symmetrical cinchona-derived
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Published 16 Sep 2024

pKalculator: A pKa predictor for C–H bonds

  • Rasmus M. Borup,
  • Nicolai Ree and
  • Jan H. Jensen

Beilstein J. Org. Chem. 2024, 20, 1614–1622, doi:10.3762/bjoc.20.144

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  • . As molecular complexity increases, this task becomes more challenging. This paper introduces pKalculator, a quantum chemistry (QM)-based workflow for automatic computations of C–H pKa values, which is used to generate a training dataset for a machine learning (ML) model. The QM workflow is
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Published 16 Jul 2024

Hypervalent iodine-catalyzed amide and alkene coupling enabled by lithium salt activation

  • Akanksha Chhikara,
  • Fan Wu,
  • Navdeep Kaur,
  • Prabagar Baskaran,
  • Alex M. Nguyen,
  • Zhichang Yin,
  • Anthony H. Pham and
  • Wei Li

Beilstein J. Org. Chem. 2024, 20, 1405–1411, doi:10.3762/bjoc.20.122

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  • of handling, and versatile reactivity, etc. render these catalysts highly attractive for adoption in organic synthesis. In particular, the field of olefin difunctionalization, known for its rapid assembly of molecular complexity, has been a fertile ground for innovation for hypervalent iodine
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Published 24 Jun 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
  • preclude chirality as in the transformation of a prochiral molecular entity into a chiral one [1]. It is a powerful and elegant strategy in asymmetric synthesis [2], which combined with the use of chiral ligands and transition-metal catalysts enabled many valuable transformations to increase molecular
  • complexity in a synthetic route. The palladium-catalyzed coupling of arenediazonium salts with olefins, the Heck–Matsuda reaction, has been instrumental in this strategy involving the desymmetrization of cyclic systems [3], especially five-membered substrates [4][5][6][7]. As we have demonstrated previously
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Published 29 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
  • , greatly increasing the molecular complexity of the starting substrate. Using radical chemistry would lead to a regioselective addition of azide radicals to the alkene, forming selectively the most stabilized C-centered radical. A prominent method for the generation of azide radicals relies on hypervalent
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Commentary
Published 03 Apr 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

Graphical Abstract
  • atom efficiency, step and pot economies, decreased number of purification steps, or protecting-group-free synthesis. Multi-step domino [1][2] and one-pot [3] reactions represent a new powerful toolbox in organic synthesis to install molecular complexity economically and sustainably, starting from
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Published 08 Feb 2024

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

Graphical Abstract
  • tool for achieving molecular complexity. Their synthetic potential has been demonstrated by their application in the total synthesis of complex natural compounds [2][4][9][10][11][12]. A remarkable example of an amino-catalyzed cascade process was reported by Enders [11], a three-component cascade
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Published 24 Aug 2023
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  • acyclic, carbocyclic, heterocyclic, and polycyclic molecular architectures with high molecular complexity. In particular, asymmetric organocatalysis plays a pivotal role in the construction of optically active, bioactive, and natural products. The main advantages of organocatalyzed stereoselective
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Published 28 Jun 2023

Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles

  • Péter Kisszékelyi and
  • Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44

Graphical Abstract
  • α,β-unsaturated carbonyl compounds [2]. In particular, the last-mentioned method is highly synthetically relevant. This approach has the advantage of being more selective and affording more molecular complexity in one step. In addition, transition-metal catalysis allows the introduction of
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Published 04 May 2023

Combining the best of both worlds: radical-based divergent total synthesis

  • Kyriaki Gennaiou,
  • Antonios Kelesidis,
  • Maria Kourgiantaki and
  • Alexandros L. Zografos

Beilstein J. Org. Chem. 2023, 19, 1–26, doi:10.3762/bjoc.19.1

Graphical Abstract
  • –2022. Review Radical-based divergent synthesis Commonly, the most successful divergent plans apply where the natural molecular complexity is rich. Not surprisingly, most of the divergent total syntheses carried out thus far are performed on terpenoid and alkaloid targets, utilizing common synthetic
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Published 02 Jan 2023

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

Graphical Abstract
  • molecular complexity. There are many examples of the organocatalytic synthesis of fused cycles starting from the cyclohexane-1,3-dione. For example, Rueping et al. demonstrated that the cyclohexane-1,3-dione undergoes a cascade reaction with α,β-unsaturated aldehydes [4] and they later employed the method
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Published 03 Feb 2022

Iron-catalyzed domino coupling reactions of π-systems

  • Austin Pounder and
  • William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

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Published 07 Dec 2021

Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances

  • Thiago S. Silva and
  • Fernando Coelho

Beilstein J. Org. Chem. 2021, 17, 1565–1590, doi:10.3762/bjoc.17.112

Graphical Abstract
  • reactions an ideal platform for the synthesis of molecules with increased molecular complexity. Keywords: hydroalkylation; hydrogen atom transfer; quaternary carbon center; radical addition; unactivated olefins; Introduction Natural product structures remain some of the main sources of inspiration for the
  • synthesis of new bioactive compounds [1][2]. A careful view of the carbon backbone of these natural molecules reveals their high molecular complexity [3][4][5], which can be described by the presence of multiple stereogenic centers in the same molecule, a substantial fraction of sp3 hybridized carbons (Fsp3
  • molecular complexity of drugs in drug discovery programs, aiming at molecules with better selectivity for biological targets [6][15][16]. One ideal way to achieve more complex molecular architectures is by hydroalkylation of olefins, a reaction that forms new C(sp3)–C(sp3) and C(sp3)–H bonds at the expense
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Published 07 Jul 2021

Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes

  • Xiaojuan Li,
  • Qiang Zhang,
  • Weigang Zhang,
  • Jinzhu Ma,
  • Yi Wang and
  • Yi Pan

Beilstein J. Org. Chem. 2021, 17, 551–557, doi:10.3762/bjoc.17.49

Graphical Abstract
  • ][16][17]. The vicinal difunctionalization of olefins to introduce two functional groups across a double bond has appeared as a powerful transformation to rapidly increase molecular complexity in synthetic chemistry with improved efficiency [18][19][20][21][22]. Various transition-metal-mediated
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Published 24 Feb 2021

Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes

  • Yajing Zhang,
  • Qingshan Tian,
  • Guozhu Zhang and
  • Dayong Zhang

Beilstein J. Org. Chem. 2020, 16, 3086–3092, doi:10.3762/bjoc.16.258

Graphical Abstract
  • vinylphosphonates from simple and commercially available alkynes proceeds under mild conditions with high stereoselectivity, and thus enabling the rapid construction of molecular complexity. Results and Discussion We investigated the reaction of phenylacetylene (1a), Selectfluor®, and diethyl phosphite to afford β
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Published 18 Dec 2020

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

  • Lucas Guillemard and
  • Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

Graphical Abstract
  • routes to afford molecular complexity from simple precursors, while concomitantly limiting the number of steps and waste generation. Following this general key objective, the landscape of organic synthesis has been clearly changed by the development of ecofriendly methodologies such as metal-catalyzed C
  • motif, have also attracted significant scientific interest [103]. Such couplings allowed constructing molecular complexity from very simple arenes such as benzene, toluene or mesitylene. However, such transformations frequently required rather harsh reaction conditions as well as the addition of strong
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Published 21 Jul 2020

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

  • Delphine Pichon,
  • Jennifer Morvan,
  • Christophe Crévisy and
  • Marc Mauduit

Beilstein J. Org. Chem. 2020, 16, 212–232, doi:10.3762/bjoc.16.24

Graphical Abstract
  • accomplished in this stimulating field. Keywords: acylimidazole; N-acyloxazolidinone; N-acylpyrrole; N-acylpyrrolidinone; aldehyde; amide; copper catalysis; electron-deficient alkenes; enantioselective conjugate addition; Michael acceptor; thioester; Introduction Generating high molecular complexity and
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Published 17 Feb 2020

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

  • Maryna V. Murlykina,
  • Oleksandr V. Kolomiets,
  • Maryna M. Kornet,
  • Yana I. Sakhno,
  • Sergey M. Desenko,
  • Victoriya V. Dyakonenko,
  • Svetlana V. Shishkina,
  • Oleksandr A. Brazhko,
  • Vladimir I. Musatov,
  • Alexander V. Tsygankov,
  • Erik V. Van der Eycken and
  • Valentyn A. Chebanov

Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126

Graphical Abstract
  • compounds characterized by several important features, e.g., molecular complexity and diversity at different levels, high variability and easy accessibility from relatively simple reagents. These challenges can be overcome by using multicomponent reactions (MCRs) but also other strategies can be applied in
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Published 12 Jun 2019

Synthesis of (macro)heterocycles by consecutive/repetitive isocyanide-based multicomponent reactions

  • Angélica de Fátima S. Barreto and
  • Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2019, 15, 906–930, doi:10.3762/bjoc.15.88

Graphical Abstract
  • of the starting materials in an atom-economic process [9][10][11]. A high level of molecular complexity can be generated in a single step and, by varying the structure of each component, different libraries of molecules can be easily obtained. Compared to a sequential synthesis, this strategy
  • of nonsymmetric cryptands by two sequential double Ugi-4CR-based macrocyclizations (Scheme 28). The approach also relies on MiBs strategy [45]. The main focus was on the use of the Ugi four-component reaction (Ugi-4CR) due to the tremendous capability of this process to generate molecular complexity
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Published 15 Apr 2019
Graphical Abstract
  • ] of norbornene derivatives with a suitably located alkynyl side-chain on the nucleus (path 2, Scheme 1) to form carbocycles has been less explored. The greatest advantage of this protocol lies in its potential in increasing the molecular complexity through Diels–Alder reaction of the resulting ring
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Published 25 Oct 2018

Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal

  • Antonio Arcadi,
  • Sandro Cacchi,
  • Giancarlo Fabrizi,
  • Francesca Ghirga,
  • Antonella Goggiamani,
  • Antonia Iazzetti and
  • Fabio Marinelli

Beilstein J. Org. Chem. 2018, 14, 2411–2417, doi:10.3762/bjoc.14.218

Graphical Abstract
  • product (Table 1, entry 10). Products substituted in the indole and quinazoline frameworks were also obtained (Table 1, entries 12–16). It is worth noting that the reaction tolerates a -Br substituent (Table 1, entries 8 and 16) which may serve as a useful handle for increasing molecular complexity
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Published 14 Sep 2018

Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies

  • Rakesh Puttreddy,
  • Ngong Kodiah Beyeh,
  • S. Maryamdokht Taimoory,
  • Daniel Meister,
  • John F. Trant and
  • Kari Rissanen

Beilstein J. Org. Chem. 2018, 14, 1723–1733, doi:10.3762/bjoc.14.146

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  • understanding of the particular interactions is required. The N-oxide oxygen atoms potential to act as a HB acceptor for multiple simultaneous N–O···(O–H)host interactions raises the molecular complexity. These are the dominant non-covalent interactions, in both the solid and solution state, compared to endo
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Published 10 Jul 2018

Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes

  • Zhensheng Zhao and
  • Graham K. Murphy

Beilstein J. Org. Chem. 2018, 14, 796–802, doi:10.3762/bjoc.14.67

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  • -chlorostyrene groups, installing them in close proximity (as shown in 3) provides two handles for rapidly achieving high-density molecular complexity. Thus, the development of strategies for their synthesis is an important endeavour. We envisioned accomplishing this by developing a chemo- and regioselective
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Published 09 Apr 2018
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