Bastien Michelet
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View article: Activation of N-containing olefins and alkynes with superacids
Activation of N-containing olefins and alkynes with superacids Open
In superacid conditions, through the capacity to generate polycationic species from functionalized organic substrates, original reactions can be conducted from unsaturated nitrogen-containing compounds, ranging from hydro- and heterofluori…
View article: Regulating the Acidity of HF/Pyridine Media to Control the Chemodivergent Fluoro- and Hydro-Heteroalkylation of Olefins
Regulating the Acidity of HF/Pyridine Media to Control the Chemodivergent Fluoro- and Hydro-Heteroalkylation of Olefins Open
Oxocarbenium ions are important reactive intermediates with many applications in organic synthesis. Among them, primary oxocarbenium ions have been much less explored, in part due to the difficulty of controlling their reactivity under sta…
View article: Glycosylium Ions in Superacid Mimic the Transition State of Enzyme Reactions
Glycosylium Ions in Superacid Mimic the Transition State of Enzyme Reactions Open
The hydrolysis of glycosides is a biochemical transformation that occurs in all living organisms, catalyzed by a broad group of enzymes, including glycoside hydrolases. These enzymes cleave the glycosidic bond via a transition state with s…
View article: Superacid-Synthesized Fluorinated Diamines Act as Selective hCA IV Inhibitors
Superacid-Synthesized Fluorinated Diamines Act as Selective hCA IV Inhibitors Open
Carbonic anhydrase (CA) IV is a membrane-bound enzyme involved in important physio-pathological processes, such as excitation-contraction coupling in heart muscle, central nervous system (CNS) extracellular buffering, and mediation of infl…
View article: Leveraging long-lived arenium ions in superacid for meta-selective methylation
Leveraging long-lived arenium ions in superacid for meta-selective methylation Open
Electrophilic aromatic substitution is one of the most mechanistically studied reactions in organic chemistry. However, precluded by innate substituent effects, the access to certain substitution patterns remains elusive. While selective C…
View article: Determination of the Hammett Acidity of HF/Base Reagents
Determination of the Hammett Acidity of HF/Base Reagents Open
Harnessing the acidity of HF/base reagents is of paramount importance to improve the efficiency and selectivity of fluorination reactions. Yet, no general method has been reported to evaluate their acidic properties, and experimental desig…
View article: Exploring Superacid‐Promoted Skeletal Reorganization of Aliphatic Nitrogen‐Containing Compounds
Exploring Superacid‐Promoted Skeletal Reorganization of Aliphatic Nitrogen‐Containing Compounds Open
Here we report a method to reorganize the core structure of aliphatic unsaturated nitrogen‐containing substrates exploiting polyprotonation in superacid solutions. The superelectrophilic activation of N ‐isopropyl systems allows for the se…
View article: Exploring Superacid‐Promoted Skeletal Reorganization of Aliphatic Nitrogen‐Containing Compounds
Exploring Superacid‐Promoted Skeletal Reorganization of Aliphatic Nitrogen‐Containing Compounds Open
Here we report a method to reorganize the core structure of aliphatic unsaturated nitrogen‐containing substrates exploiting polyprotonation in superacid solutions. The superelectrophilic activation of N ‐isopropyl systems allows for the se…
View article: CCDC 2211677: Experimental Crystal Structure Determination
CCDC 2211677: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Enantioselective Organocatalysis and Superacid Activation: Challenges and Opportunities
Enantioselective Organocatalysis and Superacid Activation: Challenges and Opportunities Open
Since the pioneer reports of the groups of Akiyama and Terada on Brønsted acid organocatalysis, this field never stopped growing with the development of ingenious strategies for the activation of challenging poorly reactive substrates. The…
View article: Leveraging Long-Lived Arenium Ions in Superacid for Meta-Selective Friedel-Crafts Methylation
Leveraging Long-Lived Arenium Ions in Superacid for Meta-Selective Friedel-Crafts Methylation Open
View article: Exploring F/CF<sub>3</sub>substituted oxocarbenium ions for the diastereoselective assembly of highly substituted tetrahydrofurans
Exploring F/CF<sub>3</sub>substituted oxocarbenium ions for the diastereoselective assembly of highly substituted tetrahydrofurans Open
We report on the dramatic effect of a local partial charge inversion by replacing a CHCH 3 group by a CFCF 3 . This strategy allows the diastereoselective reduction of 5-membered ring oxocarbenium ions to access highly substituted tetrahyd…
View article: Superacid‐Mediated Late‐Stage Aromatic Polydeuteration of Pharmaceuticals
Superacid‐Mediated Late‐Stage Aromatic Polydeuteration of Pharmaceuticals Open
The field of medicinal chemistry is currently witnessing a deuterium rush owing to the remarkable properties of this element as bioisoster of hydrogen atom. Aromatic hydrogen isotope exchange (HIE) is one of the most studied strategies now…
View article: CCDC 2028124: Experimental Crystal Structure Determination
CCDC 2028124: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Hidden Heptacyclic Chiral <i>N</i>‐Acyl Iminium Ions: A New Entry to Enantioenriched Polycyclic Azepanes and Azocanes by Superacid‐Promoted Intramolecular Pictet‐Spengler Reaction
Hidden Heptacyclic Chiral <i>N</i>‐Acyl Iminium Ions: A New Entry to Enantioenriched Polycyclic Azepanes and Azocanes by Superacid‐Promoted Intramolecular Pictet‐Spengler Reaction Open
Enantioenriched complex fused‐tricyclic azepanes or bridged‐polycyclic azocanes were constructed via a two‐step sequence involving an enantioselective organocascade followed by superacid activation of the domino adduct. The activated oxa‐b…
View article: A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides
A general synthesis of azetidines by copper-catalysed photoinduced anti-Baldwin radical cyclization of ynamides Open
View article: Modulating the Efficacy of Carbonic Anhydrase Inhibitors through Fluorine Substitution
Modulating the Efficacy of Carbonic Anhydrase Inhibitors through Fluorine Substitution Open
The insertion of fluorine atoms and/or fluoroalkyl groups can lead to many beneficial effects in biologically active molecules, such as enhanced metabolic stability, bioavailability, lipophilicity, and membrane permeability, as well as a s…
View article: Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation
Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation Open
Under superacidic conditions, aniline and indole derivatives are sulfonylated at low temperature with easy-to-access arenesulfonic acids or arenesulfonyl hydrazides. By modification of the functional-group directing effect through protonat…
View article: CCDC 2081182: Experimental Crystal Structure Determination
CCDC 2081182: Experimental Crystal Structure Determination Open
View article: CF<sub>3</sub>-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry
CF<sub>3</sub>-substituted carbocations: underexploited intermediates with great potential in modern synthetic chemistry Open
“The extraordinary instability of such an “ion” accounts for many of the peculiarities of organic reactions” – Franck C. Whitmore (1932). This statement from Whitmore came in a period where carbocations began to be considered as intermedia…
View article: Formation of synthetically relevant CF<sub>3</sub>-substituted phenonium ions in superacid media
Formation of synthetically relevant CF<sub>3</sub>-substituted phenonium ions in superacid media Open
Under superacidic conditions, CF3-substituted phenonium ions can be generated to furnish original CF3-substituted dihydrostilbenes of interest.
View article: CCDC 2014659: Experimental Crystal Structure Determination
CCDC 2014659: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Insight into the Ferrier Rearrangement by Combining Flash Chemistry and Superacids
Insight into the Ferrier Rearrangement by Combining Flash Chemistry and Superacids Open
The transformation of glycals into 2,3‐unsaturated glycosyl derivatives, reported by Ferrier in 1962, is supposed to involve an α,β unsaturated glycosyl cation, an elusive ionic species that has still to be observed experimentally. Herein,…
View article: CCDC 1994486: Experimental Crystal Structure Determination
CCDC 1994486: Experimental Crystal Structure Determination Open
View article: Access to Optically Pure Benzosultams by Superelectrophilic Activation
Access to Optically Pure Benzosultams by Superelectrophilic Activation Open
Through superacid activation, N-(arenesulfonyl)-aminoalcohols derived from readily available ephedrines or amino acids undergo an intramolecular Friedel-Crafts reaction to afford enantiopure benzosultams bearing two adjacent stereoc…
View article: Enantioenriched Methylene-Bridged Benzazocanes Synthesis by Organocatalytic and Superacid Activations
Enantioenriched Methylene-Bridged Benzazocanes Synthesis by Organocatalytic and Superacid Activations Open
View article: CCDC 1921167: Experimental Crystal Structure Determination
CCDC 1921167: Experimental Crystal Structure Determination Open
View article: Enantioenriched Methylene‐Bridged Benzazocanes Synthesis by Organocatalytic and Superacid Activations
Enantioenriched Methylene‐Bridged Benzazocanes Synthesis by Organocatalytic and Superacid Activations Open
Achieving in a straightforward way the synthesis of enantioenriched elaborated three‐dimensional molecules related to bioactive natural products remains a long‐standing quest in organic synthesis. Enantioselective organocatalysis potential…
View article: [(DPEPhos)(bcp)Cu]PF<sub>6</sub>: A General and Broadly Applicable Copper-Based Photoredox Catalyst
[(DPEPhos)(bcp)Cu]PF<sub>6</sub>: A General and Broadly Applicable Copper-Based Photoredox Catalyst Open
Our group recently reported the use of [(DPEPhos)(bcp)Cu]PF6 as a general copper-based photoredox catalyst which proved efficient to promote the activation of a broad variety of organic halides, including unactivated ones. These can then p…
View article: A General Copper-based Photoredox Catalyst for Organic Synthesis: Scope, Application in Natural Product Synthesis and Mechanistic Insights
A General Copper-based Photoredox Catalyst for Organic Synthesis: Scope, Application in Natural Product Synthesis and Mechanistic Insights Open
Organic transformations can broadly be classified into four categories including cationic, anionic, pericyclic and radical reactions. While the last category has been known for decades to provide remarkably efficient synthetic pathways, it…