104784-51-2Relevant articles and documents
Copper-free sonogashira coupling reaction using a trans-spanning 1,2-Bis(2-thienylethynyl)benzene Ligand
Atobe, Shingo,Sonoda, Motohiro,Suzuki, Yuki,Shinohara, Hiroyuki,Yamamoto, Takuya,Ogawa, Akiya
, p. 925 - 927 (2011)
Novel copper-free Sonogashira coupling reaction of aryl halides with terminal acetylenes proceeded in the presence of 1,2-bis(2-thienylethynyl) benzene (1) as a trans-bidentatable ligand.
A robust microfluidic device for the synthesis and crystal growth of organometallic polymers with highly organized structures
Liu, Xiao,Yi, Qiaolian,Han, Yongzhen,Liang, Zhenning,Shen, Chaohua,Zhou, Zhengyang,Sun, Junliang,Li, Yizhi,Du, Wenbin,Cao, Rui
, p. 1846 - 1850 (2015)
A simple and robust microfluidic device was developed to synthesize organometallic polymers with highly organized structures. The device is compatible with organic solvents. Reactants are loaded into pairs of reservoirs connected by a 15 cm long microchannel prefilled with solvents, thus allowing long-term counter diffusion for self-assembly of organometallic polymers. The process can be monitored, and the resulting crystalline polymers are harvested without damage. The device was used to synthesize three insoluble silver acetylides as single crystals of X-ray diffraction quality. Importantly, for the first time, the single-crystal structure of silver phenylacetylide was determined. The reported approach may have wide applications, such as crystallization of membrane proteins, synthesis and crystal growth of organic, inorganic, and polymeric coordination compounds, whose single crystals cannot be obtained using traditional methods.
A novel and efficient synthesis of terminal arylacetylenes via Sonogashira coupling reactions catalysed by MCM-41-supported bidentate phosphine palladium(0) complex
Wang, Yue,Huang, Bin,Sheng, Shouri,Cai, Mingzhong
, p. 728 - 732 (2007)
A variety of terminal arylacetylenes have been conveniently synthesised in good to high yields via Sonogashira coupling of aryl iodides with (trimethylsilyl)acetylene catalysed by a MCM-41-supported bidentate phosphine palladium(0) complex, followed by desilylation. The polymeric palladium catalyst can be reused many times without any decrease in activity.
Electrochemical Synthesis of 1-Naphthols by Intermolecular Annulation of Alkynes with 1,3-Dicarbonyl Compounds
He, Mu-Xue,Mo, Zu-Yu,Wang, Zi-Qiang,Cheng, Shi-Yan,Xie, Ren-Ren,Tang, Hai-Tao,Pan, Ying-Ming
, p. 724 - 728 (2020)
C-centered radical cyclization under electrochemical conditions is a feasible strategy for constructing cyclic structures. Reported herein is the electrochemical synthesis of highly functionalized 1-naphthols using alkynes and 1,3-dicarbonyl compounds by
Palladium-catalyzed cross-alkynylation of aryl bromides by sodium tetraalkynylaluminates
Gelman, Dmitri,Tsvelikhovsky, Dmitry,Molander, Gary A.,Blum, Jochanan
, p. 6287 - 6290 (2002)
Sodium tetraalkynylaluminates (1-4), prepared from NaAlH4 and terminal alkynes, cross-couple with aryl bromides in the presence of Pd(0) and Pd(II) catalysts. The reactions take place in boiling THF or DME. The process is applicable to both hom
Fluorescence properties of 1-(silylethynyl)naphthalenes and 1,4-bis(silylethynyl)naphthalenes in solutions, thin films and solid states
Maeda, Hajime,Fujii, Takayuki,Minamida, Keita,Mizuno, Kazuhiko
, p. 153 - 160 (2017)
1-(Silylethynyl)naphthalenes (1a-e) and 1,4-bis(silylethynyl)naphthalenes (2a-c) were prepared, and their fluorescence properties were evaluated in solutions, thin films and solid states. In dilute solutions, monomer emission is observed from substances in both groups and the relative fluorescence quantum yields of 1a-e increase as the steric bulk of the substituents on silicon increase. The observed concentration dependence of fluorescence intensities indicates that the self-quenching has a more pronounced effect on emission in shorter wavelength regions than that in longer wavelength regions. Analysis of Stern–Volmer type plots shows that formation of both an excimer and a termolecular excited complex is involved in fluorescence quenching of 1 in solution, whereas only an excimer is involved in quenching of 2. Fluorescence in thin films and solid states dispersion in KBr is dependent on number of silylethynyl groups present in the naphthalene derivatives. For example, excimer emission occurs from 1 while monomer emission occurs mainly from 2. X-ray crystallographic analysis of the crystal packing structure shows that 2b would have difficulty with forming an excimer because of steric hindrance, but that 2a can partially form an excimer owing to the slipped head-to-tail parallel orientation of naphthalene rings on neighboring molecules. The results of this effort demonstrate that the emission properties of 1- and 1,4-bis(silylethynyl)naphthalenes are influenced by the number of silylethynyl groups, the steric bulk of substituents on silicon atoms, and the compound's present state.
Sonogashira coupling with aqueous ammonia
Mori, Atsunori,Mohamed Ahmed, Mohamed S.,Sekiguchi, Akitoshi,Masui, Kentaro,Koike, Tooru
, p. 756 - 757 (2002)
The coupling reaction of terminal alkynes with organic halides, Sonogashira-(Hagihara) coupling, takes place with only 2 equivalents of dilute aqueous ammonia as an additive. The reaction of phenylacetylene and 4-iodoanisole in the presence of 1 mol% of P
Emission and transient absorption measurements of substitution effects of C-C triple bonds on relaxation processes of the fluorescent state of naphthalenes
Yamaji, Minoru,Maeda, Hajime,Minamida, Keita,Maeda, Tomohiro,Asai, Kengo,Konishi, Gen-Ichi,Mizuno, Kazuhiko
, p. 321 - 345 (2013)
Photophysical and photochemical properties of naphthalenes substituted with trimethylsilylethynyl, tert-butylethynyl, and trimethylsilylbutadiynyl groups were investigated by measurement of fluorescence yields, lifetimes, and triplet absorption. Introducing trimethylsilylethynyl and tert-butylethynyl groups to the 1-position of the naphthalene skeleton substantially enhanced fluorescence and intersystem crossing (ISC). The rates of fluorescence of 2-substituted naphthalenes were low. The effect of ethynyl groups on the 1-substituted naphthalenes was rationalized in terms of an increase of the transition moment along the short axis of the naphthalene skeleton. Substitution of the trimethylsilylbutadiynyl group at the 1 or 2-position of the naphthalene skeleton caused a considerable decrease in the fluorescence yield (approximately 0.01) and an increase in the ISC yield (0.99).
Formation and in situ reactions of hypervalent iodonium alkynyl triflates to form cyanocarbenes
Dempsey Hyatt,Nasrallah, Daniel J.,Maxwell, Michael A.,Hairston, A. Christina F.,Abdalhameed, Manahil M.,Croatt, Mitchell P.
, p. 5287 - 5289 (2015)
The conversion of readily available silylalkynes, iodobenzene diacetate, and azide anions was utilized to form and react cyanocarbenes. A copper(ii)-catalyzed reaction was found to react in a different manner. Both of these methods benefit from the formation and in situ reaction of hypervalent iodonium alkynyl triflates in O-H insertion reactions. This journal is
Aqueous ammonia as a new activator for Sonogashira coupling
Mohamed Ahmed, Mohamed S.,Sekiguchi, Akitoshi,Masui, Kentaro,Mori, Atsunori
, p. 160 - 168 (2005)
Sonogashira coupling, which is a coupling reaction of terminal alkynes with organic halides, takes place with dilute aqueous ammonia as an activator. The reaction of several terminal alkynes and aryl iodides in the presence of small excess of aqueous ammonia at room temperature furnishes the cross-coupling product in good-to-excellent yields. A water-soluble amine with a high boiling point is alternatively employed for reactions at higher temperatures. A related coupling reaction in the presence of carbon monoxide also proceeded at room temperature and under ambient pressure to afford α,β-alkynyl ketones efficiently.
Palladium catalysed regio- and stereoselective synthesis of (E)-4-aryl-1,3-bis(trimethylsilyl)but-3-en-1-ynes
Rogalski, Szymon,Kubicki, Maciej,Pietraszuk, Cezary
, p. 6192 - 6198 (2018)
A practical and general synthetic approach to a series of 4-aryl-but-3-en-1-ynes is described. In the presence of palladium complexes a variety of aryl bromides (or iodides) undergo coupling with two equivalents of trimethylsilylacetylene with the formati
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.).
Substituted Tetraethynylethylene–Tetravinylethylene Hybrids
Connor, Kieran P. E.,Horvath, Kelsey L.,Magann, Nicholas L.,Sherburn, Michael S.,Sowden, Madison J.,Westley, Erin
supporting information, p. 977 - 986 (2022/02/03)
A general synthetic approach to molecular structures that are hybrids of tetraethynylethylene (TEE) and tetravinylethylene (TVE) is reported. The synthesis permits the controlled preparation of many previously inaccessible structures, including examples w
