40231-03-6Relevant articles and documents
Photoinduced cis-to-trans isomerization of poly(2-ethynylthiophene) prepared with a [Rh(norbornadiene)Cl]2 catalyst. 1H NMR, UV, and ESR studies
Nakamura, Minoru,Tabata, Masayoshi,Sone, Takeyuki,Mawatari, Yasuteru,Miyasaka, Atsushi
, p. 2000 - 2004 (2002)
Poly(2-ethynylthiophene) was stereoregularly prepared with a Rh complex catalyst, [Rh-(norbornadiene)Cl]2, to selectively produce the cis-transoid isomer in high yields when triethylamine was used as the polymerization solvent at 20 °C. Photoinduced cis-to-trans isomerization was newly found to take place when the film of a pristine cis-transoid polymer was photoilluminated using a Xe lamp with light of wavelength, 320-500 nm under vacuum for 5 h. The cis and trans polymers obtained before and after the illumination were characterized in detail using 1H NMR, UV-vis of solution and film, and electron spin resonance methods.
Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes
Wang, Miao,So, Chau Ming
supporting information, p. 681 - 685 (2022/01/20)
A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.
Monosubstituted 3,3-Difluorocyclopropenes as Bench-Stable Reagents: Scope and Limitations
Nosik, Pavel S.,Pashko, Mykola O.,Poturai, Andrii S.,Kvasha, Denys A.,Pashenko, Alexander E.,Rozhenko, Alexander B.,Suikov, Sergiy,Volochnyuk, Dmitriy M.,Ryabukhin, Sergey V.,Yagupolskii, Yurii L.
, p. 6604 - 6615 (2021/12/08)
A general approach to gem-difluorocyclopropenes synthesis based on the reaction of alkynes with Ruppert-Prakash reagent is reported. The proposed method is evaluated for the synthesis of a wide difluorocyclopropenes scope based on their bench lifespan and hydrolytic stability. The tolerance of the method for common functional groups was shown. Previously unavailable difluorocyclopropenes substituted with aliphatic were prepared using the proposed procedure. The retain of stability was proven by the multigram scale synthesis and further storage in the temperature interval ?78 to ?4 °C over a year. This makes them attractive building blocks and intermediates for organic synthesis. The reasons for dropping stability were defined. The relations between the structure of the substituents and the stability of the difluorocyclopropene ring were determined and discussed.
Multi-fold Sonogashira coupling: A new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties
Islam, Khadimul,Narjinari, Himani,Bisarya, Akshara,Kumar, Akshai
, p. 9692 - 9704 (2021/11/30)
For the first time, a direct single-step one-pot route to access nine new symmetric tetraalkynylated anthracenes via Pd(CH3CN)2Cl2/cataCXiumA catalyzed tetra-fold Sonogashira coupling is reported. Five of these tetraalkynylated anthracenes have been crystallographically characterized, with two of them exhibiting multiple interactions that significantly shorten the inter-planar distances in the solid-state structure. The rich photophysical properties exhibited by these molecules hold immense promise for future applications in sensors and optoelectronic devices. Two of the considered tetraalkynylated anthracenes comprising a D-π-A-π-D motif demonstrate solvatochromism and halochromism, with one of them showing a low bandgap of 1.79 eV. The remaining compounds demonstrate bandgaps in the range of 1.79-2.04 eV.
Benzosiloles with Crystallization-Induced Emission Enhancement of Electrochemiluminescence: Synthesis, Electrochemistry, and Crystallography
Yang, Liuqing,Koo, Donghyun,Wu, Jackie,Wong, Jonathan M.,Day, Tyler,Zhang, Ruizhong,Kolongoda, Harshana,Liu, Kehan,Wang, Jian,Ding, Zhifeng,Pagenkopf, Brian L.
supporting information, p. 11715 - 11721 (2020/08/10)
Crystallization-induced emission enhancement (CIEE) was demonstrated for the first time for electrochemilunimescence (ECL) with two new benzosiloles. Compared with their solution, the films of the two benzosiloles gave CIEE of 24 and 16 times. The mechani
Aggregation induced emission-emissive stannoles in the solid state
Lork, Enno,Ramirez Y Medina, Isabel-Maria,Rohdenburg, Markus,Staubitz, Anne
supporting information, p. 9775 - 9778 (2020/09/07)
The optoelectronic and structural properties of six stannoles are reported. All revealed extremely weak emission in solution at 295 K, but intensive fluorescence in the solid state with quantum yields (ΦF) of up to 11.1% in the crystal, and of up to 24.4% (ΦF) in the thin film.
Sustainable Ligand-Free Heterogeneous Palladium-Catalyzed Sonogashira Cross-Coupling Reaction in Deep Eutectic Solvents
Messa, Francesco,Dilauro, Giuseppe,Perna, Filippo M.,Vitale, Paola,Capriati, Vito,Salomone, Antonio
, p. 1979 - 1984 (2020/02/20)
The commercially available and cheap Pd/C was found to promote Sonogashira couplings in the environmentally friendly choline chloride/glycerol eutectic mixture in the absence of external ligands. Under heterogeneous conditions, (hetero)aryl iodides were successfully coupled with both aromatic and aliphatic alkynes in yields ranging from 50 to 99 % within 3 h at 60 °C. The aforementioned catalytic system proved to be effective also towards electron-rich iodides, which are notoriously known to be poorly reactive in Pd-catalyzed Sonogashira coupling reactions. The eutectic mixture and the catalyst could easily and successfully be recycled up to four times with an E-factor as low as 24.4.
Sonogashira Couplings Catalyzed by Fe Nanoparticles Containing ppm Levels of Reusable Pd, under Mild Aqueous Micellar Conditions
Handa, Sachin,Jin, Bo,Bora, Pranjal P.,Wang, Ye,Zhang, Xiaohua,Gallou, Fabrice,Reilly, John,Lipshutz, Bruce H.
, p. 2423 - 2431 (2019/03/08)
Nanoparticles derived from FeCl3 containing the ligand XPhos and only 500 ppm Pd effect Sonogashira couplings in water between rt and 45 °C. The entire aqueous reaction medium can be easily recycled using an "in-flask" extraction. Several tande
Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis
Chiu, Hsin-Chun,Tonks, Ian A.
supporting information, p. 6090 - 6094 (2018/05/30)
Trimethylsilyl (TMS)-protected alkynes served as selective alkyne cross-coupling partners in titanium-catalyzed [2+2+1] pyrrole synthesis. Reactions of TMS-protected alkynes with internal alkynes and azobenzene under the catalysis of titanium imido comple
Intermolecular Desymmetrizing Gold-Catalyzed Yne–Yne Reaction of Push–Pull Diarylalkynes
Weingand, Vanessa,Wurm, Thomas,Vethacke, Vanessa,Dietl, Martin C.,Ehjeij, Daniel,Rudolph, Matthias,Rominger, Frank,Xie, Jin,Hashmi, A. Stephen K.
supporting information, p. 3725 - 3728 (2018/02/23)
Push–pull diaryl alkynes are dimerized in the presence of a cationic gold catalyst. The polarized structure of the applied starting materials enables the generation of a highly reactive vinyl cation intermediate in an intermolecular reaction. Trapping of the vinyl cation by a nucleophilic attack of the electron-poor aryl unit then leads to the selective formation of highly substituted naphthalenes in a single step and in complete atom economy.
