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.).
Mechanochemical Synthesis of Diarylethynes from Aryl Iodides and CaC 2
Bolm, Carsten,Van Bonn, Pit
supporting information, (2022/02/25)
A mechanochemical synthesis of diarylethynes from aryl iodides and calcium carbide as acetylene source is reported. The reaction is catalyzed by a palladium catalyst in the presence of copper salt, base, and ethanol as liquid assisting grinding (LAG) additive. Various aryl and heteroaryl iodides have been converted in up to excellent yields.
Fritsch-Buttenberg-Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes
Ando, Akane,Imafuji, Aki,Kimura, Tsutomu,Sekiguchi, Koto
, p. 1352 - 1359 (2021/06/06)
A series of 1-heteroatom-substituted vinyl p-tolyl sulfoxides were prepared and treated with organometallic reagents to evaluate which combination of sulfoxides and organometallic reagents yielded alkynes the most efficiently. The use of 1-chlorovinyl p-tolyl sulfoxide and isopropylmagnesium chloride was optimal for this purpose. A variety of 1-chlorovinyl p-tolyl sulfoxides were prepared from carbonyl compounds and chloromethyl p-tolyl sulfoxide and were converted into alkynes via the sulfoxide/magnesium exchange reaction and subsequent Fritsch-Buttenberg-Wiechell (FBW) rearrangement of the resulting magnesium alkylidene carbenoids. The mechanism of the FBW rearrangement of magnesium alkylidene carbenoids was studied by using13C-labeled sulfoxides and by using DFT calculations.
