- Synthesis of Aryl Alkynes via Copper Catalyzed Decarboxylative Alkynylation of 2-Nitrobenzoic Acids
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An efficient protocol for the synthesis of internal aryl alkynes was achieved via Cu-catalyzed decarboxylative cross-coupling reactions, and to the best of our knowledge, this is the first example of a Cu-catalyzed decarboxylative alkynylation of benzoic acids with terminal alkynes. This approach utilizes simple Cu salt as catalyst and O2, an abundant, clean, and green material, as the oxidant. The reaction tolerates various functional groups, and a variety of internal aryl alkynes were synthesized in 46-83% yields.
- Yu, Yongqi,Chen, Xiang,Wu, Qianlong,Liu, Da,Hu, Liang,Yu, Lin,Tan, Ze,Gui, Qingwen,Zhu, Gangguo
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supporting information
p. 8556 - 8566
(2018/06/29)
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- Palladium supported on amine-functionalized mesoporous silica: Highly efficient phosphine-free catalyst for alkyne-alkyne cross-coupling reaction
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An amine-functionalized mesoporous silica SBA-15 supported palladium catalyst was prepared and characterized. For the first time, this supported palladium has been used as an efficient phosphine-free and reusable catalyst for the cross-coupling of haloalkynes with terminal alkynes. A variety of haloalkynes and aromatic/aliphatic terminal alkynes were selectively coupled to afford unsymmetrical 1,4-disubstituted 1,3-diynes in good yields.
- Li, Hongling,Wang, Lailai,Yang, Min,Qi, Yanxing
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experimental part
p. 179 - 183
(2012/02/16)
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- N -alkynyl imides (ynimides): Synthesis and use as a variant of highly labile ethynamine
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This study describes the first reliable synthesis of N-alkynyl imides (ynimides). This was accomplished with a copper-catalyzed coupling reaction between alkynyl(triaryl)bismuthonium salts and five-membered imides. We also found that it was possible to utilize N-ethynyl phthalimide as a variant of the highly labile ethynamine. 4-Amino-1,2,3-triazole was successfully obtained via the CuAAC reaction of N-ethynyl phthalimide with azide followed by hydrazinolysis of the phthaloyl protecting group.
- Sueda, Takuya,Oshima, Ayumi,Teno, Naoki
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scheme or table
p. 3996 - 3999
(2011/10/01)
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- Selective Coupling Reactions of Alkynyl(phenyl)iodonium Tosylates with Alkynylcopper Reagents
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Alkynyl(phenyl)iodonium tosylates react with mixed cuprates coordinated by alkynyl components to give unsymmetrical diacetylenes selectively; the coupling reaction with dialkylcuprates afforded substituted alkynes.
- Kitamura, Tsugio,Tanaka, Toshimasa,Taniguchi, Hiroshi,Stang, Peter J.
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p. 2892 - 2893
(2007/10/02)
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- Action du chlorure de fer(III) sur des acetyleniques substitues par des elements de la colonne IVB. Formation de diynes
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We have studied the behaviour of mono- and diheterosubstituted acetylenies (1,2,3) in the presence of iron(III) chloride in a carbon tetrachloride-toluene medium at 25 deg C. 1: ; 2: ; 3: .The reaction always takes place in heterogeneous phase, the reaction medium being carefully kept free from air and humidity. Compounds of type 1. The reaction rate increases from the carbon compound to the stannyl compound. The germyl and stannyl acetylenics give 2,4-hexadiyne with good yields, respectively 62 and 84percent . Compounds of types 2 and 3. The influence of heterosubstituents on the reaction rate is the same as for compounds 1.For the mixed compound 3b, only one hexadiyne can be obtained with a yield of 90percent, gis(trimethylsilyl)buta-1,3-diyne.In the course of all these reactions, iron(III) is reduced into iron(II). The influence of the metal and its substituents as well as the action of iron chloride on the various conjugated diynes are discussed.A mechanism based on the respective reaction rates is suggested.
- Braun, Jacques,Trung, Bui Khac
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- Nickel-Catalyzed Conjugate Addition of Alkynyl Groups to α,β-Unsaturated Ketones
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The complex formed by reaction of Ni(acac)2 and DiBAH (1:1) catalyzes conjugate addition of dialkylaluminium acetylides to α,β enones; on hydrolysis, 3-alkynyl ketones are produced in high yield.Through this procedure conjugate addition of alkynyl groups
- Schwartz, Jeffrey,Carr, Denise B.,Hansen, Robert T.,Dayrit, Fabian M.
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p. 3053 - 3061
(2007/10/02)
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