2132-62-9Relevant articles and documents
Lewis acid activation of molybdenum nitrides for alkyne metathesis
Finke, Aaron D.,Moore, Jeffrey S.
, p. 7939 - 7941 (2010)
The substantial kinetic barrier to molybdenum nitride-alkyne metathesis is facilitated by precomplexation of the borane Lewis acid B(C6F 5)3, providing convenient access to metathesis-active molybdenum alkylidynes. Spectroscopic and X-ray structural analysis suggest MoN bond weakening upon borane complexation.
Synthesis of symmetrical diarylalkynes by double stille coupling of bis(tributylstannyl)acetylene
Cummins, Clark H.
, p. 857 - 860 (1994)
Treatment of bis(tributylstannyl)acetylene with two equivalents of an aryl iodide in the presence of tetrakis(triphenylphosphine)palladium (0) affords good yields of the symmetrical diarylalkyne. This approach provides a convenient and safe alternative to
Stabilizing Pentacene by Cyclopentannulation
Bheemireddy, Sambasiva R.,Ubaldo, Pamela C.,Rose, Peter W.,Finke, Aaron D.,Zhuang, Junpeng,Wang, Lichang,Plunkett, Kyle N.
, p. 15762 - 15766 (2015)
A new class of stabilized pentacene derivatives with externally fused five-membered rings are prepared by means of a key palladium-catalyzed cyclopentannulation step. The target compounds are synthesized by chemical manipulation of a partially saturated 6,13-dibromopentacene precursor that can be fully aromatized in a final step through a DDQ-mediated dehydrogenation reaction (DDQ=2,3-dichloro-5,6-dicyano-1,4-benzoquinone). The new 1,2,8,9-tetraaryldicyclopenta[fg,qr]pentacene derivatives have narrow energy gaps of circa 1.2 eV and behave as strong electron acceptors with lowest unoccupied molecular orbital energies between -3.81 and -3.90 eV. Photodegradation studies reveal the new compounds are more photostable than 6,13-bis(triisopropylsilylethynyl)pentacene (TIPS-pentacene). Five in a row: A palladium-catalyzed cyclopentannulation followed by a DDQ-mediated dehydrogenation converts a partially hydrogenated pentacene precursor into stabilized pentacenes. These pentacene derivatives are excellent electron acceptors and have small energy gaps. DDQ=2,3-dichloro-5,6-dicyano-1,4-benzoquinone.
Synthesis of symmetrical diarylalkyne from palladium-catalyzed decarboxylative couplings of propiolic acid and aryl bromides under water
Park, Kyungho,Bae, Goun,Park, Ahbyeol,Kim, Yong,Choe, Jaehoon,Song, Kwang Ho,Lee, Sunwoo
, p. 576 - 580 (2011)
Symmetric diarylalkynes were obtained from the decarboxylative coupling reactions of aryl bromides and propiolic acid in water solvent condition. In the presence of phase transfer surfactant C18H37N(CH 3)3Cl, the catalytic system of both Pd(PPh 3)2Cl2/dppb and Pd(TPPMS)2Cl 2/TPPMS afforded the desired coupled products in good yields.
The use of calcium carbide in one-pot synthesis of symmetric diaryl ethynes
Zhang, Weiwei,Wu, Huayue,Liu, Zhiqing,Zhong, Ping,Zhang, Lin,Huang, Xiaobo,Cheng, Jiang
, p. 4826 - 4828 (2006)
An efficient Pd-catalyzed copper and amine free coupling reaction of acetylene and aryl bromides was achieved with calcium carbide as an acetylene source, using inorganic base and easily prepared, air-stable aminophosphine ligand in common organic solvents, providing symmetric diaryl ethynes in one-pot with yields ranged from moderate to excellent. The Royal Society of Chemistry 2006.
Ruthenium(II)-Catalyzed Synthesis of Indolo[2,1-a]isoquinolines through Double Oxidative Annulation Reaction of Phenyl Isocyanates with Di(hetero)aryl Alkynes
Kumar, Amrendra,Kant, Ruchir,Tadigoppula, Narender
, p. 5627 - 5631 (2020)
Indole-containing polycyclic hetero aromatic compounds are synthesized by multistep process, which have wide application in biological activities and organic semi-conductor materials. Herein we report the one-pot method for the synthesis of polysubstituted indolo[2,1-a]isoquinolines by Ru(II) catalyzed double aryl/hetero aryl C(sp2)?H activation through in-situ installed carbamide of phenyl isocyanate and di(hetero)aryl substituted alkynes in the presence of Cu(OAc)2.H2O as an oxidant and CsOAc as an additive at 120 °C for 3 h in good to excellent yields. (Figure presented.).
Nickel-Catalyzed Decarbonylative Cycloaddition of Benzofuran-2,3-diones with Alkynes to Flavones
Zhang, Yu-Yang,Li, Han,Jiang, Xiaoding,Subba Reddy, Chitreddy V,Liang, Hao,Zhang, Yaqi,Cao, Rihui,Sun, Raymond Wai-Yin,Tse, Man Kin,Qiu, Liqin
supporting information, p. 525 - 530 (2021/12/22)
Using dppe as the ligand, the Nickel-catalyzed decarbonylative cycloaddition of benzofuran-2,3-diones with alkynes was established, and a variety of functional flavones were synthesized in 65–99% yields. Terminal alkynes with substituted phenyl groups and internal alkynes such as aryl acyl acetylenes and diphenylacetylenes are suitable for this reaction. The effects of bases on the reactions of different types of alkyne substrates were also investigated and discussed. (Figure presented.).
Evidence of a Photoinduced Electron-Transfer Mechanism in the Fluorescence Self-quenching of 2,5-Substituted Selenophenes Prepared through in Situ Reduction of Elemental Selenium in Superbasic Media
De Salles, Helena Domingues,Coelho, Felipe Lange,Paix?o, Douglas Bernardo,Barboza, Cristina Aparecida,Da Silveira Rampon, Daniel,Rodembusch, Fabiano Severo,Schneider, Paulo Henrique
, p. 10140 - 10153 (2021/07/31)
A series of new 2,5-disubstituted selenophene derivatives are described from elemental selenium and 1,3-diynes in superbasic media. The activation of elemental selenium in a KOH/DMSO system allows cyclization with conjugated diynes at room temperature. The cyclization reaction is extended to a broad range of functional groups, for which photophysics were experimentally and theoretically investigated. The selenophene derivatives present absorption maxima in the UV-A region and fluorescence emission in the violet-to-blue region. Fluorescence decay profiles were obtained showing a monoexponential decay with fast fluorescence lifetimes (～0.118 ns), as predicted by the Strickler-Berg relations. In general, in both investigations, no dependence on the solvent polarity on the absorption and emission maxima location was observed. On the other hand, solvents and substituents are shown to play a role in the fluorescence quantum yield values. In addition, a fluorescence self-quenching behavior could be observed, related to a photoinduced electron-transfer mechanism. Theoretical calculations performed at the MP2/ADC(2)/cc-pVDZ level of theory were performed in order to investigate the photophysical features of this series of selenophene derivatives.
