Hydrofluorination of Alkynes: From (E) to (Z)

Area of Science:

• Organic Chemistry
• Fluorine Chemistry
• Synthetic Methodology

Background:

• Hydrofluorination of alkynes yields monofluoroalkenes and difluoroalkanes.
• These fluorinated motifs are crucial in medicinal chemistry and other fields.
• Advances in synthetic routes are essential for accessing these compounds.

Purpose of the Study:

• To review recent progress in the hydrofluorination of diverse alkyne substrates.
• To explore various activation methods, including metal catalysis and metal-free conditions.
• To highlight the scope of alkyne substrates and the development of selective methods.

Main Methods:

• Review of literature on hydrofluorination reactions of alkynes.
• Categorization of methods based on activation strategies (e.g., coinage metal catalysis, metal-free).
• Analysis of substrate scope, including unactivated and activated alkynes (ynones, ynamides, alkynyl sulfides/sulfones, haloalkynes).

Main Results:

• Demonstration of efficient hydrofluorination for various alkyne types.
• Overview of regio- and stereoselective synthetic approaches.
• Identification of limitations and areas for future development in selective fluorination.

Conclusions:

• Hydrofluorination of alkynes is a versatile strategy for synthesizing organofluorine compounds.
• Significant advancements have been made using diverse catalytic and metal-free systems.
• Further research is needed to enhance regio- and stereoselectivity for all alkyne classes.