- Addition of Carbon-Fluorine Bonds to a Mg(I)-Mg(I) Bond: An Equivalent of Grignard Formation in Solution
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Addition of the carbon-fluorine bond of a series of perfluorinated and polyfluorinated arenes across the Mg-Mg bond of a simple coordination complex proceeds rapidly in solution. The reaction results in the formation of a new carbon-magnesium bond and a new fluorine-magnesium bond and is analogous to Grignard formation in homogeneous solution.
- Bakewell, Clare,White, Andrew J. P.,Crimmin, Mark R.
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supporting information
p. 12763 - 12766
(2016/10/14)
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- Synthesis of potassium 4-(1-azol-1-yl)-2,3,5,6- tetrafluorophenyltrifluoroborates from K[C6F5BF 3] and alkali metal azol-1-ides. the dramatic distinction in nucleophilicity of alkali metal azol-1-ides and dialkylamides
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Nucleophilic substitution of fluorine atom in K[C6F 5BF3] with alkali metal azol-1-ides in polar aprotic solvent (DMF, DMSO) at 60-130 C gives potassium 4-(azol-1-yl)-2,3,5,6- tetrafluorophenyltrifluoroborates, K[4-AzC6F4BF 3] (AzH = pyrrole, pyrazole, imidazole, indole, and benzimidazole). Unexpectedly, diethylamine and morpholine do not react with K[C 6F5BF3] under the same conditions while pentafluorobenzene and R2NC6F4H form at 150 C. Reaction of K[C6F5BF3] with Na[NR2] in diglyme or DMSO proceeds similar way. The assumed reason is the relatively low nucleophilicity of both secondary amines and alkali metal dialkylamides which results in destructive by-reaction with K[C6F 5BF3] rather than in its aminodefluorination. This is confirmed by the competitive nucleophilic aminodefluorination of a model substrate, C6F5Ph, with sodium indolide/sodium morpholinide.
- Shabalin, Anton Yu.,Adonin, Nicolay Yu.,Bardin, Vadim V.,Taran, Oksana P.,Ayusheev, Artemiy B.,Parmon, Valentin N.
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p. 290 - 297
(2014/01/06)
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- An aromatic glaser-hay reaction
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(Chemical Equation Presented) A general method for copper-catalyzed deprotonative dimerization of arenes by employing oxygen as the terminal oxidant has been developed. Electron-rich and electron-poor heterocycles as well as electron-poor arenes are react
- Do, Hien-Quang,Daugulis, Olafs
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supporting information; experimental part
p. 17052 - 17053
(2010/03/25)
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