Timothée Constantin
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A Halogen-Atom Transfer (XAT)-Based Approach to Indole Synthesis Using Aryl Diazonium Salts and Alkyl Iodides Open
Indoles are among the most important N-heterocycles in pharmaceuticals. Here, we present an alternative to the classic Fischer indole synthesis based on the radical coupling between aryl diazoniums and alkyl iodides. This iron-mediated str…
View article: Halogen-atom and group transfer reactivity enabled by hydrogen tunneling
Halogen-atom and group transfer reactivity enabled by hydrogen tunneling Open
The generation of carbon radicals by halogen-atom and group transfer reactions is generally achieved using tin and silicon reagents that maximize the interplay of enthalpic (thermodynamic) and polar (kinetic) effects. In this work, we demo…
View article: Applications of Halogen-Atom Transfer (XAT) for the Generation of Carbon Radicals in Synthetic Photochemistry and Photocatalysis
Applications of Halogen-Atom Transfer (XAT) for the Generation of Carbon Radicals in Synthetic Photochemistry and Photocatalysis Open
The halogen-atom transfer (XAT) is one of the most important and applied processes for the generation of carbon radicals in synthetic chemistry. In this review, we summarize and highlight the most important aspects associated with XAT and …
View article: Merging Halogen-Atom Transfer (XAT) and Cobalt Catalysis to Override E2-Selectivity in the Elimination of Alkyl Halides: A Mild Route toward <i>contra</i>-Thermodynamic Olefins
Merging Halogen-Atom Transfer (XAT) and Cobalt Catalysis to Override E2-Selectivity in the Elimination of Alkyl Halides: A Mild Route toward <i>contra</i>-Thermodynamic Olefins Open
We report here a mechanistically distinct tactic to carry E2-type eliminations on alkyl halides. This strategy exploits the interplay of α-aminoalkyl radical-mediated halogen-atom transfer (XAT) with desaturative cobalt catalysis. The meth…
View article: Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon
Radical hydroxymethylation of alkyl iodides using formaldehyde as a C1 synthon Open
Halogen-atom transfer (XAT) based on phosphoranyl radical chemistry enables the hydroxymethylation of alkyl iodides with formaldehyde.
View article: Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides
Aminoalkyl radicals as halogen-atom transfer agents for activation of alkyl and aryl halides Open
Amines as a gateway to alkyl radicals In recent years, photoredox catalysis driven by blue light has often been used to oxidize carbon centers adjacent to nitrogen. Constantin et al. now show that these aminoalkyl radicals can, in turn, co…
View article: A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry
A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry Open
Aminoalkyl radicals can be used as both initiators and chain-carriers for the conversion of aryl halides into the corresponding radicals. This approach by-passes the requirement for strongly reducing photocatalysts.