Publications by authors named "S Pillitteri"
Article Synopsis
- The Minisci reaction is an effective method for directly modifying heterocyclic molecules through C-H functionalization, relying on radical chemistry.
- It has gained popularity because its results are predictable based on the types of radicals and heterocycles used.
- The review discusses recent strategies, particularly the use of continuous flow techniques, to scale up this reaction for drug development purposes.
Article Synopsis
- - The study demonstrates the use of inactivated alkyl boronic acids (BAs) as effective partners in a photocatalyzed Suzuki-Miyaura reaction without needing external activators or strong oxidants.
- - It proposes a unique activation pathway for BAs involving a radical transfer between a bromine radical and the boron atom's empty p-orbital, which differs from traditional methods that rely on tuning oxidation potential.
- - The findings are backed by control experiments and density functional theory (DFT) calculations, introducing a new halogen radical transfer (XRT) mechanism for the reaction.
In this study, we present an inexpensive, stable, and easily available boryl radical source (BPhNa) employed in a Halogen Atom Transfer (XAT) methodology. This mild and convenient strategy unlocks the use of not only alkyl iodides as radical precursors but also of the more challenging alkyl and aryl bromides to generate C-centered radicals. The generated radicals were further engaged in the -Markovnikov hydroalkylation of electronically diverse styrenes, therefore achieving the formation of C(sp)-C(sp) and C(sp)-C(sp) bonds.
View Article and Find Full Text PDFHerein, we describe a one-pot aminoalkylation of styrene derivatives with boronic acids (BAs) and boronic acid pinacol esters as radical precursors for the synthesis of complex secondary amines in moderate to high yields through a mild and easily accessible organophotoredox-catalytic four-component reaction. Additionally, we report for the first time in a photoredox process the activation of alkyl boronic acid derivatives by imines, which play a dual role in the reaction as both substrate and Lewis base activator. The protocol applicability was greatly enhanced by its successful adaptation to photoflow reactors.
View Article and Find Full Text PDFHerein, we describe a methodology to construct polycyclic pyrrolophenanthridones with an (amino)alkyl side chain that involves visible-light-induced decarboxylative radical addition for the intermolecular dearomatization of indoles and subsequent photoinduced C(sp)-X bond activation via photoexcited ketones for an intramolecular cyclization cascade. Carboxylic acids serve both as a radical source toward indole dearomatization and as reductants to initiate an electron transfer with photoexcited -acylindole derivatives in the reaction toward pyrrolophenantridone skeletons, which occurs under mild reaction conditions with good functional group tolerance.
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