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Carboxylic Acids to Methylesters: Alkylation using Diazomethane

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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

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Introduction
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Related Experiment Video

Updated: May 25, 2025

Light-driven Enzymatic Decarboxylation

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

Continuous Flow Decarboxylative Monofluoroalkylation Enabled by Photoredox Catalysis.

Francesco Pasca¹, Yuri Gelato¹, Michael Andresini¹

¹Flow Chemistry and Microreactor Technology FLAME-Lab, Department of Pharmacy-Drug Sciences, University of Bari "A. Moro", Bari 70125, Italy.

|February 28, 2025

Summary

This study presents a scalable, mild method for monofluoroalkylation using photoredox catalysis in continuous flow. The approach efficiently introduces fluorinated fragments into diverse molecules, aiding drug discovery.

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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes

Published on: November 21, 2017

Area of Science:

Organic Chemistry
Photocatalysis
Flow Chemistry

Background:

Fluorinated organic compounds are crucial in pharmaceuticals and materials science.
Developing efficient and mild methods for introducing fluorine is a key challenge in synthetic chemistry.

Purpose of the Study:

To develop a scalable and mild strategy for monofluoroalkylation of Giese acceptors.
To utilize visible-light photoredox catalysis in continuous flow for enhanced productivity.

Main Methods:

Employing a transition-metal-free organic photocatalyst (4CzIPN).
Utilizing continuous flow technology for improved scalability and safety.
Accessing monofluoroalkyl radicals from α-monofluorocarboxylic acids.

Main Results:

Demonstrated a wide functional group tolerance under mild reaction conditions.
Successfully achieved late-stage monofluoroalkylation of biologically relevant molecules (menthol, amantadine, bepotastine, estrone derivatives).
Extended the method to a reductive multicomponent radical-polar crossover transformation for increased molecular complexity.

Conclusions:

The developed method offers a robust and versatile approach for synthesizing monofluoroalkylated compounds.
This protocol is well-suited for drug discovery programs requiring the incorporation of fluorinated motifs.
The continuous flow system enhances the practicality and efficiency of photoredox-catalyzed fluorination.