Louise Ruyet - Academia.edu (original) (raw)

Papers by Louise Ruyet

Research paper thumbnail of Integrating I(I)/I(III) catalysis in reaction cascade design enables the synthesis of gem-difluorinated tetralins from cyclobutanols

Nature Communications

Partially saturated, fluorine-containing rings are ubiquitous across the drug discovery spectrum.... more Partially saturated, fluorine-containing rings are ubiquitous across the drug discovery spectrum. This capitalises upon the biological significance of the native structure and the physicochemical advantages conferred by fluorination. Motivated by the significance of aryl tetralins in bioactive small molecules, a reaction cascade has been validated to generate novel gem-difluorinated isosteres from 1,3-diaryl cyclobutanols in a single operation. Under the Brønsted acidity of the catalysis conditions, an acid-catalysed unmasking/fluorination sequence generates a homoallylic fluoride in situ. This species serves as the substrate for an I(I)/I(III) cycle and is processed, via a phenonium ion rearrangement, to an (isolable) 1,3,3-trifluoride. A final C(sp3)-F bond activation event, enabled by HFIP, forges the difluorinated tetralin scaffold. The cascade is highly modular, enabling the intermediates to be intercepted: this provides an expansive platform for the generation of structural di...

Research paper thumbnail of Chancengerechtigkeit in der GDCh

Nachrichten aus der Chemie

Research paper thumbnail of Z-Selective Pd-catalyzed 2,2,2-trifluoroethylation of acrylamides at room temperature

Chemical Communications, 2021

A straightforward methodology for the selective synthesis of high-value added Z-2,2,2-trifluoroet... more A straightforward methodology for the selective synthesis of high-value added Z-2,2,2-trifluoroethylated acrylamides by Pd-catalyzed C–H bond activation at room temperature.

Research paper thumbnail of Transition Metal‐Free Regioselective Remote C−H Bond 2,2,2‐Trifluoroethoxylation of 8‐Aminoquinoline Derivatives at the C5 Position

European Journal of Organic Chemistry, 2021

The regioselective 2,2,2-trifluoroethoxylation at the C5 position of amides derived from the 8-am... more The regioselective 2,2,2-trifluoroethoxylation at the C5 position of amides derived from the 8-aminoquinoline has been developed. In the presence of PIDA, an unprecedented and undirected transition metal-free transformation was achieved using the readily available and appealing 2,2,2-trifluoroethanol as the fluorinated source. The selective distal 2,2,2-trifluoroethoxylation of an array of amides was achieved in moderate to good yields (12 examples, up to 61% yield). This approach provided efficient access to high-value added fluorinated quinoline derivatives, key building blocks for bulk and fine chemical industry.

Research paper thumbnail of 2,2,2‐Trifluoroethyl(mesityl)iodonium Triflate

Encyclopedia of Reagents for Organic Synthesis, 2021

Research paper thumbnail of Copper-based fluorinated reagents for the synthesis of CF2R-containing molecules (R ≠ F)

Beilstein Journal of Organic Chemistry, 2020

Over the years, the development of new methodologies for the introduction of various fluorinated ... more Over the years, the development of new methodologies for the introduction of various fluorinated motifs has gained a significant interest due to the importance of fluorine-containing molecules in the pharmaceutical and agrochemical industries. In a world eager to eco-friendlier tools, the need for innovative methods has been growing. To address these two challenges, copper-based reagents were developed to introduce CF2H, CF2RF, CF2CH3, CF2PO(OEt)2 and CF2SO2Ph motifs on a broad range of substrates. Copper-based fluorinated reagents have the advantage of being inexpensive and generally in situ generated or prepared in a few steps, which make them convenient to use. In this review, an overview of the recent advances made for the synthesis of fluorinated molecules using copper-based fluorinated reagents will be given.

Research paper thumbnail of Remote trifluoromethylthiolation of alcohols under visible light

Tetrahedron, 2020

This is a PDF file of an article that has undergone enhancements after acceptance, such as the ad... more This is a PDF file of an article that has undergone enhancements after acceptance, such as the addition of a cover page and metadata, and formatting for readability, but it is not yet the definitive version of record. This version will undergo additional copyediting, typesetting and review before it is published in its final form, but we are providing this version to give early visibility of the article. Please note that, during the production process, errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.

Research paper thumbnail of Distal Construction of a Carbon‐SCF 2 R Bond on Aliphatic Alcohols Enabled by 1,5‐Hydrogen‐Atom Transfer

Advanced Synthesis & Catalysis, 2022

Research paper thumbnail of Integrating I(I)/I(III) catalysis in reaction cascade design enables the synthesis of gem-difluorinated tetralins from cyclobutanols

Nature Communications

Partially saturated, fluorine-containing rings are ubiquitous across the drug discovery spectrum.... more Partially saturated, fluorine-containing rings are ubiquitous across the drug discovery spectrum. This capitalises upon the biological significance of the native structure and the physicochemical advantages conferred by fluorination. Motivated by the significance of aryl tetralins in bioactive small molecules, a reaction cascade has been validated to generate novel gem-difluorinated isosteres from 1,3-diaryl cyclobutanols in a single operation. Under the Brønsted acidity of the catalysis conditions, an acid-catalysed unmasking/fluorination sequence generates a homoallylic fluoride in situ. This species serves as the substrate for an I(I)/I(III) cycle and is processed, via a phenonium ion rearrangement, to an (isolable) 1,3,3-trifluoride. A final C(sp3)-F bond activation event, enabled by HFIP, forges the difluorinated tetralin scaffold. The cascade is highly modular, enabling the intermediates to be intercepted: this provides an expansive platform for the generation of structural di...

Research paper thumbnail of Chancengerechtigkeit in der GDCh

Nachrichten aus der Chemie

Research paper thumbnail of Z-Selective Pd-catalyzed 2,2,2-trifluoroethylation of acrylamides at room temperature

Chemical Communications, 2021

A straightforward methodology for the selective synthesis of high-value added Z-2,2,2-trifluoroet... more A straightforward methodology for the selective synthesis of high-value added Z-2,2,2-trifluoroethylated acrylamides by Pd-catalyzed C–H bond activation at room temperature.

Research paper thumbnail of Transition Metal‐Free Regioselective Remote C−H Bond 2,2,2‐Trifluoroethoxylation of 8‐Aminoquinoline Derivatives at the C5 Position

European Journal of Organic Chemistry, 2021

The regioselective 2,2,2-trifluoroethoxylation at the C5 position of amides derived from the 8-am... more The regioselective 2,2,2-trifluoroethoxylation at the C5 position of amides derived from the 8-aminoquinoline has been developed. In the presence of PIDA, an unprecedented and undirected transition metal-free transformation was achieved using the readily available and appealing 2,2,2-trifluoroethanol as the fluorinated source. The selective distal 2,2,2-trifluoroethoxylation of an array of amides was achieved in moderate to good yields (12 examples, up to 61% yield). This approach provided efficient access to high-value added fluorinated quinoline derivatives, key building blocks for bulk and fine chemical industry.

Research paper thumbnail of 2,2,2‐Trifluoroethyl(mesityl)iodonium Triflate

Encyclopedia of Reagents for Organic Synthesis, 2021

Research paper thumbnail of Copper-based fluorinated reagents for the synthesis of CF2R-containing molecules (R ≠ F)

Beilstein Journal of Organic Chemistry, 2020

Over the years, the development of new methodologies for the introduction of various fluorinated ... more Over the years, the development of new methodologies for the introduction of various fluorinated motifs has gained a significant interest due to the importance of fluorine-containing molecules in the pharmaceutical and agrochemical industries. In a world eager to eco-friendlier tools, the need for innovative methods has been growing. To address these two challenges, copper-based reagents were developed to introduce CF2H, CF2RF, CF2CH3, CF2PO(OEt)2 and CF2SO2Ph motifs on a broad range of substrates. Copper-based fluorinated reagents have the advantage of being inexpensive and generally in situ generated or prepared in a few steps, which make them convenient to use. In this review, an overview of the recent advances made for the synthesis of fluorinated molecules using copper-based fluorinated reagents will be given.

Research paper thumbnail of Remote trifluoromethylthiolation of alcohols under visible light

Tetrahedron, 2020

This is a PDF file of an article that has undergone enhancements after acceptance, such as the ad... more This is a PDF file of an article that has undergone enhancements after acceptance, such as the addition of a cover page and metadata, and formatting for readability, but it is not yet the definitive version of record. This version will undergo additional copyediting, typesetting and review before it is published in its final form, but we are providing this version to give early visibility of the article. Please note that, during the production process, errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.

Research paper thumbnail of Distal Construction of a Carbon‐SCF 2 R Bond on Aliphatic Alcohols Enabled by 1,5‐Hydrogen‐Atom Transfer

Advanced Synthesis & Catalysis, 2022