Functionalization of Alkenes through Telescoped Continuous Flow Aziridination Processes

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Flow Chemistry

Background:

• Aziridination of alkenes is a crucial transformation in organic synthesis.
• Handling and isolation of reactive aziridine intermediates can be challenging and hazardous.
• Continuous flow chemistry offers advantages for managing reactive intermediates.

Purpose of the Study:

• To develop an efficient and safe method for alkene aziridination.
• To integrate aziridine generation with subsequent nucleophilic ring-opening reactions.
• To synthesize challenging and highly reactive aziridine compounds.

Main Methods:

• Utilized highly soluble iminoiodane derivatives for aziridination.
• Employed continuous flow reactor systems for the reactions.
• Combined aziridine formation with in situ nucleophilic ring-opening.

Main Results:

• Achieved efficient aziridination of alkenes under continuous flow conditions.
• Successfully generated and reacted aziridines without isolation.
• Synthesized a variety of products through one-pot procedures.
• Enabled the use of aziridines that are difficult to isolate due to high reactivity.

Conclusions:

• Continuous flow aziridination using soluble iminoiodanes is a viable and safe synthetic strategy.
• This approach simplifies the synthesis of complex molecules by avoiding intermediate isolation.
• The methodology expands access to highly reactive aziridine intermediates for further functionalization.