- In Situ Generation of Alkynylzinc and Its Subsequent Negishi Reaction in a Flow Reactor
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A highly efficient and convenient Negishi cross-coupling reaction has been developed for the synthesis of unsymmetrical alkynes and enynes in a continuous-flow process. The reaction proceeds through an in situ generated alkynylzinc reagent by the reaction of lithium acetylide with zinc halide at room temperature followed by a cross-coupling reaction with aryl or vinyl iodides. The notable features of this work compared to the conventional benchtop method are mild reaction conditions, good to excellent yields, broad functional-group compatibility, short residence time (73 sec) and especially desilylation of TMS group with the residence time of only 10.5 sec.
- Kandasamy, Mohanraj,Huang, Yu- Hsuan,Ganesan, Balaji,Senadi, Gopal Chandru,Lin, Wei-Yu
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p. 4349 - 4356
(2019/07/03)
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- External oxidant-free cross-coupling of arylcopper and alkynylcopper reagents leading to arylalkyne
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External oxidant-free oxidative cross-coupling between arylcopper and alkynylcopper has been performed, which provides a new way for the formation of arylalkyne with high selectivity.
- Wang, Sheng,Min, Yaosen,Zhang, Xiaowei,Xi, Chanjuan
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p. 28308 - 28312
(2017/07/07)
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- Splitting a Substrate into Three Parts: Gold-Catalyzed Nitrogenation of Alkynes by C-C and C≡C Bond Cleavage
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A gold-catalyzed nitrogenation of alkynes for the synthesis of carbamides and amino tetrazoles through C-C and C≡C bond cleavages is described. A diverse set of functionalized carbamide and amino tetrazole derivatives were selectively constructed under mild conditions. The chemoselectivity can be easily switched by the selection of the acid additives. The reaction is characterized by its broad substrate scope, direct construction of high value products, easy operation under air, and mild conditions at room temperature. This chemistry provides a way to transform alkynes by splitting the substrate into three parts.
- Qin, Chong,Su, Yijin,Shen, Tao,Shi, Xiaodong,Jiao, Ning
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supporting information
p. 350 - 354
(2016/01/25)
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- Facile synthesis of substituted alkynes by nano-palladium catalyzed oxidative cross-coupling reaction of arylboronic acids with terminal alkynes
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The oxidative cross-coupling of terminal alkynes with arylboronic acids catalyzed by the porous palladium nanospheres was developed. In the presence of silver oxide, triphenylphosphine and cesium carbonate, the reaction provided the corresponding arylalkynes with good to excellent yields. There were also other obvious advantages such as broad applicability, high selectivity, simple experimental operation as well as the convenient preparation, high efficiency and reusability of catalyst. The possible mechanism of this transition-metal nanoparticles catalyzed oxidative cross-coupling reaction of two nucleophiles was proposed.
- Nie, Xiaopeng,Liu, Suli,Zong, Yan,Sun, Peipei,Bao, Jianchun
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experimental part
p. 1570 - 1573
(2011/06/17)
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- Highly active palladium catalyst for the sonogashira coupling reaction of unreactive aryl chlorides
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This communication reports on the β-diketiminatophosphane palladium-catalyzed copper-free Sonogashira coupling of aryl chlorides with alkynes. A catalyst loading of 0.5 mol% is sufficient to achieve high performance under relatively mild reaction conditio
- Lee, Dong-Hwan,Kwon, Young-Jun,Jin, Myung-Jong
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supporting information; experimental part
p. 3090 - 3094
(2012/01/03)
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- Palladium-catalyzed aerobic oxidative cross-coupling reactions of terminal alkynes with alkylzinc reagents
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Chemical Equation Represented With air as the oxidant, terminal alkynes can be directly cross-coupled with alkylzinc reagents in the presence of a Pd catalyst at room temperature. CO was found to be critical in gaining high chemical yields and selectivities. A wide range of alkynes and alkylzinc reagents were tested, and good to excellent yields were obtained. Copyright
- Chen, Mao,Zheng, Xiaolong,Li, Wenqing,He, Jun,Lei, Aiwen
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supporting information; experimental part
p. 4101 - 4103
(2010/05/14)
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- Copper-catalyzed alkyne-aryne coupling reaction under microwave conditions: preparation of unsymmetric and symmetric di-substituted alkynes
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Several unsymmetric and symmetric alkynes were prepared excellent to modest yields by generating benzyne from the reaction of 2-(trimethylsilyl)phenyl triflate with CsF in the presence of CuI and terminal alkyne under microwave heating for 30 min at 150 °
- Akubathini, Shashidhar Kumar,Biehl, Ed
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scheme or table
p. 1809 - 1811
(2009/07/05)
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- Iron-catalyzed arylmagnesiation of aryl(alkyl)acetylenes in the presence of an N-heterocyclic carbene ligand
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(Chemical Equation Presented) Addition of arylmagnesium bromides to aryl(alkyl)acetylenes proceeded in the presence of an iron catalyst and a N-heterocyclic carbene ligand to give high yields of the corresponding alkenylmagnesium reagents, which were transformed into tetrasubstituted alkenes by subsequent treatment with electrophiles.
- Yamagami, Takafumi,Shintani, Ryo,Shirakawa, Eiji,Hayashi, Tamio
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p. 1045 - 1048
(2007/10/03)
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- Process for preparing alkynyl-substituted aromatic and heterocyclic compounds
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Mono- and disubstituted aryl or heterocyclic acetylenes are produced by a process comprising reacting an aryl nitrile with an alkynylzinc compound, a bis-alkynylzinc compound, or an alkynylmagnesium compound, in the presence of a nickel/phosphine catalyst.
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Page/Page column 10
(2010/02/12)
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- Synthesis of isoindolo[2,1-α]indoles by the palladium-catalyzed annulation of internal acetylenes
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A wide variety of substituted isoindolo[2,1-α]indoles have been prepared via annulation of internal alkynes by imines derived from o-iodoanilines in the presence of a palladium catalyst. This methodology provides an extremely efficient route for the synth
- Roesch,Larock
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p. 412 - 420
(2007/10/03)
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- One-Pot Conversion of Phenols to Arenes
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In the presence of a fluoroalkanesulfonyl fluoride and a catalytic amount of bis(triphenylphosphine)palladium dichloride, phenols reacted with triethylammonium formate in triethylamine to give arenes.Similarly, phenols reacted with alkynes or alkenes in triethylamine providing alkynyl- or alkenylarenes, respectively.
- Chen, Qing-Yun,He, Ya-Bo
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p. 896 - 897
(2007/10/02)
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- A NOVEL METHOD FOR CARBON-CARBON BOND FORMATION PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF PHENYL FLUOROALKANESULFONATES WITH ORGANOZINC REAGENTS
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Cross-coupling reaction of phenyl fluoroalkanesulfonates with three kinds of organozinc reagents in the presence of palladium gives the corresponding alkylbenzenes in good yields.A possible mechanism is suggested.
- Chen, Qing-Yun,He, Ya-Bo
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p. 2387 - 2388
(2007/10/02)
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