22779-05-1Relevant articles and documents
New non-protienogenic fluorescent amino acids: Benzoxazol-5-yl-alanine derivatives containing acetylene unit. Synthesis, spectral and photophysical properties
Bylińska, Irena,Guzow, Katarzyna,Wójcik, Justyna,Wiczk, Wies?aw
, p. 679 - 685 (2018)
New derivatives of non-proteinogenic amino acids benzoxazol-5-yl-alanine containing substituted acetylene derivative were synthesized according to Sonogashira coupling reaction. All of the obtained compounds are fluorescent. They are characterized by high or moderate molar absorption coefficients, large Stokes shifts, high fluorescence quantum yields and very high brightness. All of these parameters as well as the positions of absorption and emission bands depend on the type and size of substituent and the solvent polarity. Their high brightness enables working with low concentrations, simple and easy detection of spectral absorption and fluorescence analyzes. Moreover, amino acid part of studied compounds allow to use them as covalently attached to a peptide or protein fluorescent probes in biological system studies.
CuI-catalyzed homocoupling of terminal alkynes to 1,3-diynes
Yin, Kun,Li, Chun-Ju,Li, Jian,Jia, Xue-Shun
, p. 16 - 20 (2011)
A simple and efficient protocol for CuI-catalyzed oxidative homocoupling reaction of terminal alkynes to symmetrical 1,4-disubstituted 1,3-diynes was reported. The reaction can be carried out in the open air, using NaOAc as a base in the absence of any other additives. A variety of terminal alkynes were converted to the corresponding 1.3-diynes in good to excellent yields without any side product formation. Copyright
UV-irradiated formation of diradicals of diphenylbutadiyne and some of its p,p′-disubstituted derivatives
Beristain, Miriam F.,Fomine, Sergei,Munoz, Eduardo,Salcedo, Roberto,Ogawa, Takeshi
, p. 1986 - 1993 (2005)
It was found for the first time that aromatic diacetylenes give strong ESR signals of stable carbon radical species in solution or in the solid state upon irradiation of UV light. The numbers of radicals reached to the order of 10 20 radicals p
Copper(I)-catalyzed cross-coupling reaction of Alkynylsilanes with 1- chloroalkynes
Nishihara, Yasushi,Ikegashira, Kazutaka,Mori, Atsunori,Hiyama, Tamejiro
, p. 4075 - 4078 (1998)
A variety of unsymmetrical 1,4-biaryl-1,3-butadiyne derivatives are synthesized by a copper(I)-catalized cross-coupling reaction of alkynylsilanes with 1-chloroalkynes in moderate to good yields. These reactions are derived from the transmetalation of an alkynyl group from silicon to copper in a polar solvent.
Cooperative Palladium and Copper Catalysis: One-pot Synthesis of Diamino-Substituted Naphthalenes from Aryl Halides, 1,4-Bis(trimethylsilyl)butadiyne and Amines
Li, Yuan,Qiu, Shaozhong,Fan, Ling,Yin, Guodong
, p. 1230 - 1235 (2020)
A one-pot method for the preparation of diamino-substituted naphthalene derivatives from easily available starting materials aryl halides, 1,4-bis(trimethylsilyl)butadiyne and amines is developed. Two C?N bonds, three C?C bonds and one aromatic ring are f
Transition-Metal-Free Alkynylation of 2-Oxindoles through Radical-Radical Coupling
Huang, Hong-Yan,Cheng, Liang,Liu, Jie-Jie,Wang, Dong,Liu, Li,Li, Chao-Jun
, p. 2656 - 2663 (2017)
An effective transition-metal-free approach for the synthesis of 3-alkynyl-2-oxindoles through a radical-radical coupling process was developed. The reaction was general with respect to 2-oxindoles and iodoalkynes and provided the desired products bearing a quaternary center at C3 in good to excellent yields, making this method synthetically viable and attractive for the synthesis of spiro and fused 2-oxindole derivatives.
Palladium mediated direct coupling of silylated arylalkynes with propargylic chlorides: an efficient access to functionalized conjugated allenynes
Girard, Delphine,Broussous, Sylvie,Provot, Olivier,Brion, Jean-Daniel,Alami, Mouad
, p. 6022 - 6026 (2007)
Pd/Cu-catalyzed one-pot reaction of 1-trimethylsilyl-2-arylalkynes with propargylic chlorides in the presence of TBAF is described. The present new procedure is applicable to a wide range of silylated arylalkynes with both electron-withdrawing and electro
Application of the polyacrylonitrile fiber as a novel support for polymer-supported copper catalysts in terminal alkyne homocoupling reactions
Shi, Xian-Lei,Hu, Qianqian,Wang, Fang,Zhang, Wenqin,Duan, Peigao
, p. 233 - 239 (2016)
A commercially available synthetic polyacrylonitrile fiber, capable of acting as a novel support for polymer-supported copper catalyst in terminal alkyne homocoupling reactions, is presented. Detailed characterization by inductively coupled plasma (ICP) analysis, Fourier transform infrared spectroscopy (FTIR), and scanning electron microscopy (SEM) confirmed the changes and stability of the fiber catalyst during the modification and utilization processes. Moreover, the catalytic reactions proceeded at room temperature using air as a green oxidant to afford nearly quantitative yields (95-99%); the fiber catalyst has shown excellent activity and superior recyclability (over 16 cycles); and the procedure is operationally simple and amenable to the gram scale in continuous-flow processing. Furthermore, the prominent features (high strength, good flexibility, etc.) of the polyacrylonitrile fiber make the fiber-supported catalyst very attractive for fixed-bed reactors in the chemical industry.
A mild and efficient palladium-catalyzed homocoupling of lithium alkynyltriisopropoxyborates: A new route to synthesis of 1,3-diynes
Oh, Chang Ho,Reddy, V. Raghava
, p. 5221 - 5224 (2004)
Lithium alkynyltriisopropoxyborates were homocoupled in the presence of palladium acetate and DPEPhos. This protocol allows a new efficient route to synthesis of 1,3-diynes under very mild conditions.
Cu-Catalyzed solvent-free, pot-economic synthesis of 1,3-dynes from 1,1-dibromoalkenes in the presence of DBU?H2O
Moodapelly, Shiva Krishna,Nanaji, Yerramsetti,Sharma, Gangavaram V.M.,Suneeel, Kanaparthy,Doddi, Venkata Ramana
, (2021/05/27)
An efficient synthesis of 1,3-diynes directly from 1,1-dibromoalkenes has been achieved by utilizing hydrated 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU.H2O) as a sole reagent and a catalyst CuI. In general, 1,3-diynes were synthesized from corresponding terminal alkynes, which in turn were obtained from 1,1-dibromoalkenes. The DBU.H2O allowed the synthesis of 1,3-diynes not only in a pot-efficient manner but also under solvent-free conditions at ambient temperature. A plausible mechanism is proposed via 1-bromoalkynes intermediate instead of terminal alkynes.