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View article: A Radical Cascade with Double Intramolecular Hydrogen Atom Transfer for the Generation of Bisfunctionalized Cyclopentanes from Linear Alkynes
A Radical Cascade with Double Intramolecular Hydrogen Atom Transfer for the Generation of Bisfunctionalized Cyclopentanes from Linear Alkynes Open
Radical cascade reactions represent a powerful synthetic tool for the preparation of complex molecules from easily assembled starting materials. The incorporation of an intramolecular hydrogen atom transfer step in the cascade enhances con…
View article: A Radical Cascade with Double Intramolecular Hydrogen Atom Transfer for the Generation of Bisfunctionalized Cyclopentanes from Linear Alkynes
A Radical Cascade with Double Intramolecular Hydrogen Atom Transfer for the Generation of Bisfunctionalized Cyclopentanes from Linear Alkynes Open
Radical cascade reactions represent a powerful synthetic tool for the preparation of complex molecules from easily assembled starting materials. The incorporation of an intramolecular hydrogen atom transfer step in the cascade enhances con…
View article: A Radical Cascade with Double Intramolecular Hydrogen Atom Transfer for the Generation of Bisfunctionalized Cyclopentanes from Linear Alkynes.
A Radical Cascade with Double Intramolecular Hydrogen Atom Transfer for the Generation of Bisfunctionalized Cyclopentanes from Linear Alkynes. Open
Radical cascade reactions represent a powerful synthetic tool for the preparation of complex molecules from easily assembled starting materials. The incorporation of an intramolecular hydrogen atom transfer step in the cascade enhances con…
View article: Easy Access to γ-Iodo-gem-Diborylated-Cyclopentanes and Bicyclic Cyclopropanes
Easy Access to γ-Iodo-gem-Diborylated-Cyclopentanes and Bicyclic Cyclopropanes Open
A formal atom transfer radical [3+2] annulation (ATRAn) reaction between different homoallyl radical precursors and 1,1-diborylethene was developed. It provides a rapid access to polysubstituted cyclopentanes containing a gem-diboronic est…
View article: CCDC 2264981: Experimental Crystal Structure Determination
CCDC 2264981: 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: Borylated Cyclopentanes via Atom Transfer Radical [3+2] Annulation
Borylated Cyclopentanes via Atom Transfer Radical [3+2] Annulation Open
An atom transfer radical [3+2] annulation (ATRAn) reaction involving alkenyl boronic esters and homoallylic iodides provides a rapid access to polysubstituted borylated cyclopentanes. A variety of α-substituted vinylboronic esters are suit…
View article: Intramolecular Asymmetric Cyclopropanation Using Air Stable Alkylboronic Esters
Intramolecular Asymmetric Cyclopropanation Using Air Stable Alkylboronic Esters Open
The preparation of polysubstituted bicyclo[3.1.0]hexanes starting from air stable substituted pent-4-en-1-ylboronic esters has been investigated. The method involves a Matteson homologation with LiCHCl2 leading to intermediates 1-chlorohex…
View article: Traceless Thioacid-Mediated Radical Cyclization of 1,6-Dienes
Traceless Thioacid-Mediated Radical Cyclization of 1,6-Dienes Open
[Image: see text] Five-membered ring systems are ubiquitous throughout natural products and synthetic therapeutics, and thus, efficient methods to access this essential scaffold are required. Herein, we report the thioacid-mediated, 5-exo-…
View article: Radical Mediated Hydroperfluoroalkylation of Unactivated Alkenes
Radical Mediated Hydroperfluoroalkylation of Unactivated Alkenes Open
The direct hydroperfluoroalkylation of a wide range of unactivated alkenes have been achieved at room temperature with readily available iodoperfluoroalkanes using 4-tert-butylcatechol as a source of hydrogen atom and triethylborane. The h…
View article: Fine Tuning of Quantum Dots Photocatalysts for the Synthesis of Tropane Alkaloid Skeletons**
Fine Tuning of Quantum Dots Photocatalysts for the Synthesis of Tropane Alkaloid Skeletons** Open
Several types of Quantum Dots (QDs) (CdS, CdSe and InP, as well as core‐shell QDs such as type I InP‐ZnS, quasi type‐II CdSe‐CdS and inverted type‐I CdS‐CdSe) were considered for generating α‐aminoalkyl free radicals. The feasibility of th…
View article: Fine tuning of quantum dots photocatalysts for the synthesis of tropane alkaloid skeletons
Fine tuning of quantum dots photocatalysts for the synthesis of tropane alkaloid skeletons Open
Several types of Quantum Dots (QDs) (CdS, CdSe and InP, as well as core-shell QDs such as type I InP-ZnS, quasi type-II CdSe-CdS and inverse type-I CdS-CdSe) were considered for generating α-aminoalkyl free radicals. The feasibility of the…
View article: CCDC 2111680: Experimental Crystal Structure Determination
CCDC 2111680: 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: Tropane and related alkaloid skeletons via a radical [3+3]-annulation process
Tropane and related alkaloid skeletons via a radical [3+3]-annulation process Open
Tropanes and related bicyclic alkaloids are highly attractive compounds possessing a broad biological activity. Here we report a mild and simple protocol for the synthesis of N -arylated 8-azabicyclo[3.2.1]octane and 9-azabicyclo[3.3.1]non…
View article: Tropane and Related Alkaloid Skeletons via a Radical [3+3]-Annulation Process
Tropane and Related Alkaloid Skeletons via a Radical [3+3]-Annulation Process Open
A mild and simple protocol for the synthesis of 8-azabicyclo[3.2.1]octane and 9-azabicyclo[3.3.1]nonane derivatives is described. It provides these valuable bicyclic alkaloid skeletons in good yields and high levels of diastereoselectivity…
View article: Tropane and Related Alkaloid Skeletons via a Radical [3+3]-Annulation Process
Tropane and Related Alkaloid Skeletons via a Radical [3+3]-Annulation Process Open
A mild and simple protocol for the synthesis of 8-azabicyclo[3.2.1]octane and 9-azabicyclo[3.3.1]nonane derivatives is described. It provides these valuable bicyclic alkaloid skeletons in good yields and high levels of diastereoselectivity…
View article: Forskolin Editing via Radical Iodo- and Hydroalkylation
Forskolin Editing via Radical Iodo- and Hydroalkylation Open
The modification of highly oxygenated forskolin as well as manoyl and epi-manoyl oxide, two less functionalized model substrates sharing the same polycyclic skeleton, via intermolecular carbon-centered radical addition to the vinyl moiety …
View article: Radical chain monoalkylation of pyridines
Radical chain monoalkylation of pyridines Open
N -Methoxypyridinium salts are exceptionally reactive radical traps that can be used in efficient radical chain reactions with organoboranes.
View article: Intermolecular Radical C–H Bond Activation: A Powerful Tool for Late Stage Functionalization
Intermolecular Radical C–H Bond Activation: A Powerful Tool for Late Stage Functionalization Open
The synthesis of complex molecules via radical reactions involving carbon–carbon and carbon–heteroatom bonds has become a very successful approach. Radical chemistry has long been dominated by the use of tin-based reagents. Those strongly …
View article: Linked PDF of Table of Contents
Linked PDF of Table of Contents Open
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View article: Radical-Mediated Reactions of α-Bromo Aluminium Thioacetals, α-Bromothioesters, and Xanthates for Thiolactone Synthesis
Radical-Mediated Reactions of α-Bromo Aluminium Thioacetals, α-Bromothioesters, and Xanthates for Thiolactone Synthesis Open
Thiolactones have attracted considerable attention in recent years as bioactive natural products, lead compounds for drug discovery, molecular probes, and reagents for polymerisation. We have investigated radical-mediated C-C bond forming …
View article: CCDC 1811948: Experimental Crystal Structure Determination
CCDC 1811948: 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: Memory of chirality in reactions involving monoradicals
Memory of chirality in reactions involving monoradicals Open
The effects of memory of chirality (MoC) in reactions involving monoradical species are reviewed here. Reactions involving a nonracemic chiral starting material bearing a single stereogenic element such as a chiral center or chiral axis di…
View article: Effect of Brønsted acids on the thiophenol-mediated radical addition–translocation–cyclization process for the preparation of pyrrolidine derivatives
Effect of Brønsted acids on the thiophenol-mediated radical addition–translocation–cyclization process for the preparation of pyrrolidine derivatives Open
A thiophenol-mediated method for the conversion of propargylamines to pyrrolidines under acidic conditions is described. This cascade reaction involves addition of a thiyl radical to the terminal alkyne followed by a 1,5-hydrogen transfer …
View article: Radical Cyclisation of α‐Halo Aluminium Acetals: A Mechanistic Study
Radical Cyclisation of α‐Halo Aluminium Acetals: A Mechanistic Study Open
α‐Bromo aluminium acetals are suitable substrates for Ueno–Stork‐like radical cyclisations affording γ‐lactols and acid‐sensitive methylene‐γ‐lactols in high yields. The mechanistic study herein sets the scope and limitation of this reacti…
View article: Chemoselective access to substituted butenolides via a radical cyclization pathway: mechanistic study, limits and application
Chemoselective access to substituted butenolides via a radical cyclization pathway: mechanistic study, limits and application Open
We developed a new approach to γ-lactols and methylene-γ-lactols based upon the radical cyclization of aluminium acetals obtained by reduction of α-bromoesters with DIBAL-H. The cyclic aluminium acetals resulting from the cyclization proce…