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

• 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

Biphenylene-containing polycyclic conjugated compounds

• Cagatay Dengiz

Beilstein J. Org. Chem. 2023, 19, 1895–1911, doi:10.3762/bjoc.19.141

• through Sonogashira cross-coupling reactions with alkynes featuring different protecting groups such as TIPS, TES, and TIBS. Scheme 7 illustrates the derivatization process using one of the chosen examples, specifically the TIPS group. Accordingly, the cross-coupling products 33a–c were obtained in yields

Simple synthesis of multi-halogenated alkenes from 2-bromo-2-chloro-1,1,1-trifluoroethane (halothane)

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

Beilstein J. Org. Chem. 2022, 18, 1567–1574, doi:10.3762/bjoc.18.167

• presence of KOH. In this reaction, halothane plays a key role in the construction of highly halogenated and structurally intriguing products. The tri-halogenated alkenyl ether has potential applications in organic chemistry, e.g., in Suzuki–Miyaura or Sonogashira cross-coupling reactions. Further

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• exceptional versatility [13][14][15]. Therefore, the low cost first series transition metals such as iron and cobalt show higher significance than other transition metals. Naturally, Sonogashira cross-coupling reactions using cobalt or iron catalysts were reported as more cost-effective alternatives to the

• -azaindole derivatives under microwave irradiation that helps to reduce the reaction time and minimizes side product formation. Co-catalyzed Sonogashira cross-coupling reactions Nanoparticle-based protocols The advantages of using immobilized catalysts include the possibility of the catalyst to be easily

• clearly shown that the complex of Co-N-heterocyclic ligand exhibits a higher activity. Sonogashira cross-coupling reactions were also reported by making use of a heterogeneous, efficient and green cobalt catalyst obtained through complexation of cobalt with methyl salicylate-functionalized chitosan fibres

Visible-light-mediated copper photocatalysis for organic syntheses

• Yajing Zhang,
• Qian Wang,
• Zongsheng Yan,
• Donglai Ma and
• Yuguang Zheng

Beilstein J. Org. Chem. 2021, 17, 2520–2542, doi:10.3762/bjoc.17.169

• promising, scalable green process that can be used as an alternative to the conventional Sonogashira cross-coupling reactions. In 2018, Lalic and co-workers [66] extended this approach to alkyl halides and reported the photoinduced copper-catalyzed Sonogashira coupling of alkynes and alkyl iodide 21. The

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

• Paola Vitale,
• Luciana Cicco,
• Ilaria Cellamare,
• Filippo M. Perna,
• Antonio Salomone and
• Vito Capriati

Beilstein J. Org. Chem. 2020, 16, 1915–1923, doi:10.3762/bjoc.16.158

• ], (c) carbon–sulfur bond-forming reactions [9], (d) directed ortho-metalation and nucleophilic acyl substitution strategies [10], (e) Pd-catalyzed aminocarbonylation of aryl iodides, Suzuki–Miyaura and Sonogashira cross-coupling reactions [11][12][13], (f) Cu-catalyzed C–N coupling reactions [14], and

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

Towards triptycene functionalization and triptycene-linked porphyrin arrays

• Gemma M. Locke,
• Keith J. Flanagan and
• Mathias O. Senge

Beilstein J. Org. Chem. 2020, 16, 763–777, doi:10.3762/bjoc.16.70

• complexes such as 2 were synthesized by us with the purpose of conducting electron transfer studies [25]. Both Suzuki and Sonogashira cross-coupling reactions were employed to realize this new class of triptycene-linked trimeric porphyrins. The three porphyrins, or three BODIPYs in 2 were either linked

• of various porphyrin/BODIPY dimers with different linker groups in CHCl3. The excitation for compounds 9, 7, 19 and 20 was λ = 433 (23095), 370 (27027), 455 (21978) and 450 (22222) nm (cm−1), respectively. Sonogashira cross-coupling reactions to form symmetric porphyrin and BODIPY triptycene-linked

• dyads. Sonogashira cross-coupling reactions to form a triptycene-substituted porphyrin monomer and an unsymmetrically substituted triptycene-linked porphyrin dyad. Synthesis of the triptycene-porphyrin-triptycene complex 18. Supporting Information Supporting Information File 172: Experimental details

Structure–property relationships and third-order nonlinearities in diketopyrrolopyrrole based D–π–A–π–D molecules

• Jan Podlesný,
• Lenka Dokládalová,
• Oldřich Pytela,
• Adam Urbanec,
• Milan Klikar,
• Numan Almonasy,
• Tomáš Mikysek,
• Jaroslav Jedryka,
• Iwan V. Kityk and
• Filip Bureš

Beilstein J. Org. Chem. 2017, 13, 2374–2384, doi:10.3762/bjoc.13.235

• in modular way prepared by Suzuki–Miyaura, Migita–Stille, and Sonogashira cross-coupling reactions. The chromophores differ in the π-system extension as well as in the peripheral substitution. The thermal stability of 1–5 is mostly affected by the presence of acetylene linkers, 1,4-phenylene and 2,5

Transition-metal-free one-pot synthesis of alkynyl selenides from terminal alkynes under aerobic and sustainable conditions

• Adrián A. Heredia and
• Alicia B. Peñéñory

Beilstein J. Org. Chem. 2017, 13, 910–918, doi:10.3762/bjoc.13.92

• synthesis of seleno-functionalized heterocycles [20][21]. Recently, the use of alkynyl selenides as substrates for Pd-catalyzed Suzuki, Negishi, Kumada and Sonogashira cross-coupling reactions has been reported with good yields [22]. Due to the synthetic relevance of alkynyl selenides several methodologies

Synthesis of 3,4-dihydro-1,8-naphthyridin-2(1H)-ones via microwave-activated inverse electron-demand Diels–Alder reactions

• Salah Fadel,
• Youssef Hajbi,
• Mostafa Khouili,
• Said Lazar,
• Franck Suzenet and
• Gérald Guillaumet

Beilstein J. Org. Chem. 2014, 10, 282–286, doi:10.3762/bjoc.10.24

• with different amines. Substitution of 1,2,4-triazine 1 by different amides 2–5. Intramolecular inverse electron-demand Diels–Alder reactions under microwave irradiation. Sonogashira cross-coupling reactions from alkynes 6–9. Intramolecular inverse electron-demand Diels–Alder reactions of substituted

Synthesis, photophysical and electrochemical characterization of terpyridine-functionalized dendritic oligothiophenes and their Ru(II) complexes

• Amaresh Mishra,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2013, 9, 866–876, doi:10.3762/bjoc.9.100

• Amaresh Mishra Elena Mena-Osteritz Peter Bauerle Institute of Organic Chemistry II and Advanced Materials, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany 10.3762/bjoc.9.100 Abstract Pd-catalyzed Sonogashira cross-coupling reactions were used to synthesize novel π-conjugated

• Syntheses. A modular approach was selected for the synthesis of the targeted metallodendrimers, consisting of (1) the preparation of dendrons by employing Sonogashira cross-coupling reactions, (2) their functionalization with tpy-ligands, and (3) formation of the corresponding homoleptic Ru(II) complexes

Synthesis of multivalent host and guest molecules for the construction of multithreaded diamide pseudorotaxanes

• Nora L. Löw,
• Egor V. Dzyuba,
• Boris Brusilowskij,
• Lena Kaufmann,
• Elisa Franzmann,
• Wolfgang Maison,
• Emily Brandt,
• Daniel Aicher,
• Arno Wiehe and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2012, 8, 234–245, doi:10.3762/bjoc.8.24

• Berlin, Germany 10.3762/bjoc.8.24 Abstract A series of di-, tri- and tetravalent axles and wheels for the synthesis of pseudorotaxanes bearing the tetralactam macrocycle/diamide axle binding motif was prepared. Starting from iodinated monovalent precursors, Sonogashira cross-coupling reactions were

• (wheel)N–H···O=C(axle) hydrogen bonds. Through the iodine substituents, both building blocks can be connected to appropriate spacers in Sonogashira cross-coupling reactions [102]. This coupling strategy creates rather rigid connections to the spacers and helps in reducing the entropic penalties that

• Discussion Synthesis of monovalent precursors Although aryl bromides, triflates and sometimes even chlorides react efficiently in Sonogashira cross-coupling reactions, our previous studies [103][104] showed that only the iodinated TLM, and in some rare cases the corresponding triflate-substituted wheel, is

Imidazole as a parent π-conjugated backbone in charge-transfer chromophores

• Jiří Kulhánek and
• Filip Bureš

Beilstein J. Org. Chem. 2012, 8, 25–49, doi:10.3762/bjoc.8.4

• chromophores 95–100 (Figure 18; [112]). The synthesis of this series of chromophores involved two-fold Suzuki–Miyaura and Sonogashira cross-coupling reactions on dibromoolefin 94 (for X-ray structure see [113]). This compound proved to be a very useful, fully planar precursor for the construction of a

Impact of the level of complexity in self-sorting: Fabrication of a supramolecular scalene triangle

• Kingsuk Mahata and
• Michael Schmittel

Beilstein J. Org. Chem. 2011, 7, 1555–1561, doi:10.3762/bjoc.7.183

• ] (Figure 1). The coordination behaviour of molecular component 3 was integrated into 5, the latter being synthesised in a Sonogashira homocoupling reaction [27]. The information stored in 1 and 4 was instated in the unsymmetrical bisphenanthroline 6, readily accessible by stepwise Sonogashira cross

• -coupling reactions [15]. A known procedure was followed to prepare the terpyridine–phenanthroline hybrid 7 [8]. The lengths of the ligands were chosen in such a way that they provide the geometrically different sides of a scalene triangle. Results and Discussion We tested both self-sorting algorithms as

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• ,β-unsaturated ketones generated in situ by Pd-catalyzed Sonogashira cross-coupling reactions. For instance, by building on their expertise in this area [14] Müller and coworkers recently developed a very effective and modular three-component strategy to assemble a series of 3,5-bis(hetero)aromatic