- Rapid access to β-trifluoromethyl-substituted ketones: Harnessing inductive effects in wacker-type oxidations of internal alkenes
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We present a practical trifluoromethyl-directed Wacker-type oxidation of internal alkenes that enables rapid access to β-trifluoromethyl-substituted ketones. Allylic trifluoromethyl-substituted alkenes bearing a wide range of functional groups can be oxidized in high yield and regioselectivity. The distance dependence of the regioselectivity was established by systematic variation of the number of methylene units between the double bond and the trifluoromethyl group. The regioselectivity enforced by traditional directing groups could even be reversed by introduction of a competing trifluoromethyl group. Besides being a new powerful synthetic method to prepare fluorinated molecules, this work directly probes the role of inductive effects on nucleopalladation events.
- Lerch, Michael M.,Morandi, Bill,Wickens, Zachary K.,Grubbs, Robert H.
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supporting information
p. 8654 - 8658
(2014/08/18)
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- Method for producing 4,4,4- Trifluorobutane-2-One
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The present invention provides a novel method for preparing 4,4,4-trifluorobutane-2-one by providing a fluorobutene selected from the group consisting of 2,4,4,4-tetrafluoro-1-butene, (E)-1,1,1,3-tetrafluoro-2-butene, (Z)-1,1,1,3-tetrafluoro-2-butene, and mixture thereof; and reacting the fluorobutene(s) with a proton acid and water.
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Page/Page column 9
(2009/09/26)
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- A METHOD FOR PRODUCING 4,4,4-TRIFLUOROBUTANE-2-ONE
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The present invention provides a novel method for preparing 4,4,4-trifluorobutane-2-one by providing a fluorobutene selected from the group consisting of 2,4,4,4-tetrafluoro-1-butene, (E)- 1,1,1,3-tetrafluoro-2-butene, (Z)-1,1,1,3-tetrafluoro-2-butene, and mixture thereof; and reacting the fluorobutene(s) with a proton acid and water.
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Page/Page column 33-34
(2008/06/13)
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- Allyl esters substituted by a difluoromethylene group, their process of synthesis and their use, and a process for functionalizing a double bond
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This invention provides compounds of formula: in which Rf is a radical that carries a perfluoromethylene group, which group ensures bonding to the remainder of the molecule; R1 and R3, which can be the same or different, are chosen from among hydrogen and alkyl or aryl radicals; Ψ is an electroattractor group such that Ψ-O—H is an acid whose pKa (in water) is at most equal to 8, advantageously 6, and preferably 5. These compounds are useful for the synthesis of nitrogen-containing heterocyclic compounds.
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