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A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

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Fluoro-Substituted Methyllithium Chemistry: External Quenching Method Using Flow Microreactors.

Marco Colella¹, Arianna Tota¹, Yusuke Takahashi²

¹Department of Pharmacy-Drug Sciences, Flow Chemistry and Microreactor Technology FLAME-Lab, University of Bari "A. Moro", Via E. Orabona 4, 70125, Bari, Italy.

Angewandte Chemie (International Ed. in English)

|April 3, 2020

Summary

External quenching in flow microreactors enables the use of short-lived fluorinated organometallic reagents. This breakthrough facilitates highly chemoselective reactions for synthesizing novel fluorinated molecules.

Keywords:

amides flow chemistry lithium microreactor reactive intermediates

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Area of Science:

Organic Chemistry
Fluorine Chemistry
Synthetic Methodology

Background:

Short-lived organometallic reagents are challenging to utilize in synthesis.
Fluorinated organic compounds are crucial in pharmaceuticals and materials science.
Developing efficient methods for incorporating fluorine is a key area of research.

Purpose of the Study:

To develop a method for generating and using short-lived fluorinated organometallic reagents.
To explore the synthetic utility of these reagents in chemoselective reactions.
To expand the toolkit for synthesizing complex fluorinated molecules.

Main Methods:

Utilizing an external quenching technique within flow microreactors.
Generation of fluoromethyllithium, fluoroiodomethyllithium, and fluoroiodostannylmethyllithium reagents.
Performing chemoselective reactions with the generated organometallic species.

Main Results:

Successful generation and in situ use of short-lived fluorinated organometallic reagents.
Demonstration of highly chemoselective transformations.
Expansion of synthetic routes to diverse fluorinated compounds.

Conclusions:

The external quenching method in flow microreactors is effective for handling unstable fluorinated organometallics.
This approach provides new opportunities for the synthesis of valuable fluorinated molecules.
The developed methodology enhances the accessibility of fluorinated organometallic chemistry.