- Catalytic One-Step Deoxytrifluoromethylation of Alcohols
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A new bench-stable trifluoromethylation reagent, phenyl bromodifluoroacetate, converts readily available alcohols to trifluoromethanes in a Cu-catalyzed deoxytrifluoromethylation reaction. This reaction streamlines access to target biologically active molecules, and should be useful for a variety of medicinal, agricultural, and materials chemists.
- Azambuja, Francisco De,Lovrien, Sydney M.,Ross, Patrick,Ambler, Brett R.,Altman, Ryan A.
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p. 2061 - 2071
(2019/05/16)
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- Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes
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(Chemical Equation Presented) "Cu-CF3" species have been used historically for a broad spectrum of nucleophilic trifluoromethylation reactions. Although recent advancements have employed ligands to stabilize and harness the reactivity of this key organometallic intermediate, the ability of a ligand to differentiate a regiochemical outcome of a Cu-CF3-mediated or -catalyzed reaction has not been previously reported. Herein, we report the first example of a Cu-catalyzed trifluoromethylation reaction in which a ligand controls the regiochemical outcome. More specifically, we demonstrate the ability of bipyridyl-derived ligands to control the regioselectivity of the Cu-catalyzed nucleophilic trifluoromethylation reactions of propargyl electrophiles to generate (trifluoromethyl)allenes. This method provides a variety of di-, tri-, and tetrasubstituted (trifluoromethyl)allenes, which can be further modified to generate complex fluorinated substructures.
- Ambler, Brett R.,Peddi, Santosh,Altman, Ryan A.
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p. 2506 - 2509
(2015/05/27)
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- Copper-catalyzed decarboxylative trifluoromethylation of propargyl bromodifluoroacetates
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The development of efficient methods for accessing fluoA rinated functional groups is desirable. Herein, we report a two step method that utilizes catalytic copper for the decarboxylative trifluoromethylation of propargyl bromodifluoroacetates is described. This protocol affords a mixture of propargyl trifluoromethanes and trifluoromethyl allenes. Georg Thieme Verlag Stuttgart New York.
- Ambler, Brett R.,Peddi, Santosh,Altman, Ryan A.
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p. 1938 - 1946
(2014/07/22)
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