Multifaceted Strategy for the Synthesis of Diverse  2,2'-Bithiophene Derivatives

Krompiec, Stanisław; Filapek, Michał; Grudzka-Flak, Iwona; Słodek, Aneta; Kula, Sławomir; Małecki, Jan Grzegorz; Malarz, Joanna; Szafraniec‐Gorol, Grażyna; Penkala, Mateusz; Schab‐Balcerzak, Ewa; Paluch, Marian; Mierzwa, M.; Matussek, Marek; Szłapa, Agata; Pająk, Michał; Blach, Dariusz; Marcol, Beata; Danikiewicz, Witold; Boharewicz, Bartosz; Iwan, Agnieszka

doi:10.3390/molecules20034565

Cited by 16 publications

(22 citation statements)

References 89 publications

(119 reference statements)

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“…Halogenated internal alkynes can be employed to form 5-halo-1,2,3-triazoles and will be discussed in the next section . An internal bisbithiophenyl alkyne also has been applied in RuAAC with good results …”

Section: Methodology Substrates and Catalystsmentioning

confidence: 99%

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

et al. 2016

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The ruthenium-catalyzed azide alkyne cycloaddition (RuAAC) affords 1,5-disubstituted 1,2,3-triazoles in one step and complements the more established copper-catalyzed reaction providing the 1,4-isomer. The RuAAC reaction has quickly found its way into the organic chemistry toolbox and found applications in many different areas, such as medicinal chemistry, polymer synthesis, organocatalysis, supramolecular chemistry and the construction of 2 electronic devices. This review discusses the mechanism, scope and applications of the RuAAC reaction, covering the literature during the last 10 years. CONTENTS

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Section: Methodology Substrates and Catalystsmentioning

confidence: 99%

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

et al. 2016

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“…The above‐mentioned fluoranthenes 2 a – 2 f were synthesized according to a reported method based on the Diels–Alder reaction between substituted acetylenes and 1,8‐(diphenylethynyl)naphthalene, as reported by Siegel and co‐workers . We successfully applied this method previously for the synthesis of fluoranthenes containing two 2,2′‐bithienyl substituents . In this present study, we used substrates containing not only a single acetylene motif (Scheme ), but also substrates with two ethynyl motifs, thus allowing us to obtain products with two fluoranthene cores (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…[18,19] We successfully appliedt his method previously for the synthesis of fluoranthenes containing two 2,2'-bithienyl substituents. [20] In this present study,w eu sed substrates containing not only as ingle acetylene motif (Scheme1), but also substrates with two ethynyl motifs, thus allowing us to obtain products with two fluoranthene cores (Scheme 2). This type of compound is usually obtained by using thermal Diels-Alder reactions of diacetylenes with cyclopentadienone derivatives.…”

Section: Synthesis and Structure Determinationmentioning

confidence: 94%

Luminescent‐Substituted Fluoranthenes—Synthesis, Structure, Electrochemistry, and Optical Properties

Słodek

Maroń

Pająk

et al. 2018

Chemistry A European J

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Six novel fluoranthene derivatives, namely, three terminally substituted and three bis(fluoranthene) units with fluorene, bithiophene, and carbazole spacers, were obtained through [2+2+2] cycloaddition and characterized completely. Based on the conducted studies, the obtained derivatives can be classified as donor-acceptor (D-A) and acceptor-donor-acceptor (A-D-A) systems, in which the fluoranthene unit acts as an electron-withdrawing unit. The optical results revealed that novel fluoranthene derivatives absorb light in the range λ=236-417 nm, which originates from a π→π transition within the conjugated system. The compounds exhibit fluorescence that range from deep blue to green, which mainly arises from intramolecular charge transfer (ICT) states. High Stoke shifts and high quantum yields in solution (ϕ=0.22-0.57) and in the solid state (ϕ=0.18-0.44) have been observed for fluoranthene derivatives. All the derivatives display multistep oxidation processes at low potentials. The electronic structure of the presented compounds is additionally supported by time-dependent DFT computations.

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“…Although these pyrrole-ring formation reactions are also known to proceed in the presence of KOH [83], the synthetic utility of the process, exemplified with the preparation of compounds 56-61 featuring interesting photophysical properties (see Figure 9), has only been demonstrated using catalytic CuCl [84][85][86][87][88][89]. In all the cases, the central pyrrolic unit was generated through the initial copper-catalyzed annulation of a primary amine with a 1,3-diynic system.…”

Section: Hydroamination and Hydroamidation Processesmentioning

confidence: 99%

Catalytic Hydrofunctionalization Reactions of 1,3-Diynes

Cadierno

2022

Catalysts

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Metal-catalyzed hydrofunctionalization reactions of alkynes, i.e., the addition of Y–H units (Y = heteroatom or carbon) across the carbon–carbon triple bond, have attracted enormous attention for decades since they allow the straightforward and atom-economic access to a wide variety of functionalized olefins and, in its intramolecular version, to relevant heterocyclic and carbocyclic compounds. Despite conjugated 1,3-diynes being considered key building blocks in synthetic organic chemistry, this particular class of alkynes has been much less employed in hydrofunctionalization reactions when compared to terminal or internal monoynes. The presence of two C≡C bonds in conjugated 1,3-diynes adds to the classical regio- and stereocontrol issues associated with the alkyne hydrofunctionalization processes’ other problems, such as the possibility to undergo 1,2-, 3,4-, or 1,4-monoadditions as well as double addition reactions, thus increasing the number of potential products that can be formed. In this review article, metal-catalyzed hydrofunctionalization reactions of these challenging substrates are comprehensively discussed.

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Multifaceted Strategy for the Synthesis of Diverse 2,2'-Bithiophene Derivatives

Cited by 16 publications

References 89 publications

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications

Luminescent‐Substituted Fluoranthenes—Synthesis, Structure, Electrochemistry, and Optical Properties

Catalytic Hydrofunctionalization Reactions of 1,3-Diynes

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