772-38-3Relevant academic research and scientific papers
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.).
Ligand-free (: Z)-selective transfer semihydrogenation of alkynes catalyzed by in situ generated oxidizable copper nanoparticles
Grela, Karol,Kusy, Rafa?
supporting information, p. 5494 - 5502 (2021/08/16)
Herein, we present (Z)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a green protic solvent. This environmentally friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the completion of a semihydrogenation reaction results in the formation of a water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need for any special regeneration processes. Formed NH4B(OR)4 can be easily transformed back into ammonia-borane or into boric acid. In addition, a one-pot tandem sequence involving a Suzuki reaction followed by semihydrogenation was presented, which allows minimization of chemical waste production.
Dense Alkyne Arrays of a Zr(IV) Metal-Organic Framework Absorb Co(CO) for Functionalization
Cheng, Shengxian,Diao, Yingxue,He, Jun,Hu, Jieying,Hu, Xiangzi,Li, Mu-Qing,Li, Yang Yang,Ma, Feixiang,Xu, Zhengtao
supporting information, (2020/04/10)
Finely dispersed Co(0) and CoO species were efficiently loaded into a stable metal-organic framework to impart catalytic activities to the porous solid. The metalation of the MOF host is facilitated by the dense arrays of accessible alkyne units that boost the alkyne-Co(CO) interaction. The tetrakis(4-carboxylphenylethynyl)pyrene linker, with eight symmetrically backfolded alkyne side arms, features strong fluorescence and a dendritic Sierpinski shape. The resultant Zr(IV)-MOF features NU-901 topology (scu net, with rhombus channels) and breathing properties (e.g., the contracted (porous) phase reverts to the as-made phase upon contact with DMF (dimethylformamide)). The inserted Co(CO) guests quickly react with air to form atomically dispersed CoO species (nondiffracting), and subsequent thermal treatment at 600 °C of the CoO-loaded solid generates an electrocatalyst for the oxygen evolution reaction (OER).
Efficient Multigram Approach to Acetylenes and CF3-ynones Starting from Dichloroalkenes Prepared by Catalytic Olefination Reaction (COR)
Muzalevskiy, Vasiliy M.,Sizova, Zoia A.,Diusenov, Arstan I.,Shastin, Alexey V.,Nenajdenko, Valentine G.
supporting information, p. 4161 - 4166 (2020/07/13)
A novel approach to terminal acetylenes based on catalytic olefination reaction COR of arylaldehydes to form dichloroalkenes followed by treatment with nBuLi was elaborated. This method is atom economical and displays high yields and effectivity. The corresponding alkynes can be prepared in up to 97 % yield. One pot procedure towards CF3-ynones was elaborated to provide these products in up to 87 % yield starting from dichloroalkenes.
Regioselective Gold-Catalyzed Hydration of CF3- and SF5-alkynes
Cloutier, Mélissa,Roudias, Majdouline,Paquin, Jean-Fran?ois
supporting information, p. 3866 - 3870 (2019/05/24)
The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.
SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes
Zha, Gao-Feng,Fang, Wan-Yin,Li, You-Gui,Leng, Jing,Chen, Xing,Qin, Hua-Li
supporting information, p. 17666 - 17673 (2019/01/04)
Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).
Metal-free synthesis of imidazole by BF3·Et2O promoted denitrogenative transannulation of N-sulfonyl-1,2,3-triazole
Yang, Dongdong,Shan, Lihong,Xu, Ze-Feng,Li, Chuan-Ying
, p. 1461 - 1464 (2018/03/08)
BF3·Et2O promoted metal-free denitrogenative transannulation of N-sulfonyl-1,2,3-triazole was reported. Rather than transition metals, BF3·Et2O was employed for the first time to promote the formation of α-diazoimines from N-sulfonyl-1,2,3-triazoles in nitriles, leading to the synthesis of various imidazoles. The protocol tolerates a broad range of functional groups and could also be applied to the late-stage modification of bioactive molecules, demonstrating the potential of this protocol in organic synthesis. A plausible mechanism was proposed.
Palladium-catalyzed tandem C-H functionalization/cyclization strategy for the synthesis of 5-hydroxybenzofuran derivatives
Ichake, Sachin S.,Konala, Ashok,Kavala, Veerababurao,Kuo, Chun-Wei,Yao, Ching-Fa
supporting information, p. 54 - 57 (2017/11/28)
A palladium-catalyzed benzoquinone C-H functionalization/ cyclization strategy with terminal alkynes was employed for the synthesis of some biologically relevant 2, 3-disubstituted 5-hydroxybenzofuran derivatives. The benzoquinone acts as a reactant as well as an oxidant. During the process, an additional alkyne functionality can be introduced at the C3 position of the benzofuran. Base, ligand, and external oxidant are not required in this protocol.
Reaction discovery using acetylene gas as the chemical feedstock accelerated by the stop-flow micro-tubing reactor system
Xue, Fei,Deng, Hongping,Xue, Chengwen,Mohamed, Dara Khairunnisa Binte,Tang, Karen Yuanting,Wu, Jie
, p. 3623 - 3627 (2017/07/11)
Acetylene gas has been applied as a feedstock under transition-metal catalysis and photo-redox conditions to produce important chemicals including terminal alkynes, fulvenes, and fluorinated styrene compounds. The reaction discovery process was accelerated through the use of stop-flow micro-tubing reactors. This reactor prototype was developed by joining elements from both continuous micro-flow and conventional batch reactors, which was convenient and effective for gas/liquid reaction screening. Notably, the developed transformations were either inefficient or unsuccessful in conventional batch reactors. Its success relies on the unique advantages provided by this stop-flow micro-tubing reactor system.
Copper(I)-catalyzed stereoselective hydrogenation of 1,3-diynes and enynes
Thiel, Niklas O.,Kemper, Sebastian,Teichert, Johannes F.
, p. 5023 - 5028 (2017/07/27)
A stereoselective hydrogenation of 1,3-diynes with an air-stable copper(I)/N-heterocyclic carbene complex, [IPrCuOH], has been developed. The corresponding products, 1,3-dienes, are obtained in a stereoselective manner depending on their substitution pattern: Diaryl-diynes yield E,E-1,3-dienes, whereas dialkyl-diynes are converted to the corresponding Z,Z-1,3-dienes. Hydrogenation and deuteration experiments with enynes indicate that these are competent reaction intermediates in the hydrogenation of diynes.
