Catalytic Hydrotrifluoromethylation of Unactivated Alkenes

Mizuta, Satoshi; Verhoog, Stefan; Engle, Keary M.; Khotavivattana, Tanatorn; O’Duill, Miriam; Wheelhouse, Katherine; Rassias, Gerasimos; Médebielle, Maurice; Gouverneur, Véronique

doi:10.1021/ja401022x

Programmable Deuteration of Indoles via Reverse Deuterium Exchange (2023)
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Methods for selective deuterium incorporation into drug-like molecules have become extremely valuable due to the commercial, mechanistic, and biological importance of deuterated compounds. Herein, we report a programmable labeling platform that allow... Read More about Programmable Deuteration of Indoles via Reverse Deuterium Exchange.

Frontispiece: A Guide to Directing Group Removal: 8‐Aminoquinoline (2021)
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A Guide to Directing Group Removal: 8?Aminoquinoline (2021)
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The use of directing groups allows high levels of selectivity to be achieved in transition metal‐catalyzed transformations. Efficient removal of these auxiliaries after successful functionalization, however, can be very challenging. This review provi... Read More about A Guide to Directing Group Removal: 8?Aminoquinoline.

Controlling the crystal structure of precisely spaced polyethylene-like polyphosphoesters (2020)
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Understanding polymer crystallization is important for polyethylene-like materials. A small fraction of monomers with functional groups within the polyethylene chain can act as crystallization “defects”. Such defects can be used to control the crysta... Read More about Controlling the crystal structure of precisely spaced polyethylene-like polyphosphoesters.

Protodepalladation as a Strategic Elementary Step in Catalysis (2018)
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Protodepalladation is the redox-neutral conversion of a C–Pd(II) bond into a C–H bond via reaction with a Brønsted acid. It is the microscopic reverse of Pd(II)-mediated C–H cleavage. In the context of catalytic reaction development, protodepalladati... Read More about Protodepalladation as a Strategic Elementary Step in Catalysis.

Copper-Catalyzed Chan–Lam Cyclopropylation of Phenols and Azaheterocycles (2018)
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Small molecules containing cyclopropane-heteroatom linkages are commonly needed in medicinal chemistry campaigns yet are problematic to prepare using existing methods. To address this issue, a scalable Chan-Lam cyclopropylation reaction using potassi... Read More about Copper-Catalyzed Chan–Lam Cyclopropylation of Phenols and Azaheterocycles.

Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization (2017)
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Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselectiv... Read More about Tridentate Directing Groups Stabilize 6-Membered Palladacycles in Catalytic Alkene Hydrofunctionalization.

Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl (2017)
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A regioselective anti-hydrochlorination of unactivated alkynes is reported. The reaction utilizes in situ generated HCl as the source of both the Cl - and H + and is catalyzed by palladium(II) acetate, with loadings as low as 25 ppm. Removable picoli... Read More about Palladium(II)-Catalyzed Directed anti-Hydrochlorination of Unactivated Alkynes with HCl.

ChemInform Abstract: Cross-Coupling of [2-Aryl-1,1,2,2-Tetrafluoroethyl](trimethyl)silanes with Aryl Halides. (2015)
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No abstract is available for this article.

Cross-Coupling of [2-Aryl-1,1,2,2-tetrafluoroethyl](trimethyl)silanes with Aryl Halides (2015)
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The synthesis of arylCF2CF2SiMe3 and their reactivity in cross-coupling reactions with aryl iodides and aryl bromides to afford a range of 1,1,2,2-tetrafluoro-1,2-arylethanes is reported. The use of pyridine as an alternative to phenanthroline, and t... Read More about Cross-Coupling of [2-Aryl-1,1,2,2-tetrafluoroethyl](trimethyl)silanes with Aryl Halides.

Recruitment and Immobilization of a Fluorinated Biomarker Across an Interfacial Phospholipid Film using a Fluorocarbon Gas (2015)
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Perfluorohexane gas when introduced in the air atmosphere above a film of phospholipid self-supported on an aqueous solution of C2F5-labeled compounds causes the recruitment and immobilization of the latter in the interfacial film. When the phospholi... Read More about Recruitment and Immobilization of a Fluorinated Biomarker Across an Interfacial Phospholipid Film using a Fluorocarbon Gas.

ChemInform Abstract: Catalytic Hydrotrifluoromethylation of Unactivated Alkenes (2013)
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Treatment of readily available α,α-difluoro- and α-fluoroarylacetic acids with Selectfluor under Ag(I) catalysis led to decarboxylative fluorination. This operationally simple reaction gave access to tri- and difluoromethylarenes applying a late-stag... Read More about Catalytic Decarboxylative Fluorination for the Synthesis of Tri- and Difluoromethyl Arenes.

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A new catalytic method to access allylic secondary CF3 products is described. These reactions use the visible light excited Ru(bpy)3Cl2·6H2O catalyst and the Togni or Umemoto reagent as the CF3 source. The photoredox catalytic manifold delivers enant... Read More about Trifluoromethylation of Allylsilanes under Photoredox Catalysis.

Catalytic Hydrotrifluoromethylation of Unactivated Alkenes (2013)
Journal Article

A visible-light-mediated hydrotrifluoromethylation of unactivated alkenes that uses the Umemoto reagent as the CF3 source and MeOH as the reductant is disclosed. This effective transformation operates at room temperature in the presence of 5 mol % Ru... Read More about Catalytic Hydrotrifluoromethylation of Unactivated Alkenes.

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