Aminoarylation of alkynes using diarylanilines

Area of Science:

• Organic Chemistry
• Synthetic Chemistry

Background:

• Direct C-N bond formation is crucial in organic synthesis.
• Existing methods often rely on transition metal catalysis or organometallic reagents.
• Aniline derivatives offer potential for novel synthetic transformations.

Purpose of the Study:

• To develop a novel intermolecular aminoarylation of alkynes.
• To achieve this transformation without transition metal catalysts or organometallic reagents.
• To demonstrate the utility of the generated products as building blocks.

Main Methods:

• Addition of diarylanilines to alkynes.
• Smiles-Truce rearrangement.
• Direct manipulation of the C-N bond in anilines.

Main Results:

• Successful intermolecular aminoarylation of alkynes was achieved.
• The reaction proceeds via a Smiles-Truce rearrangement mechanism.
• No organometallic reagents or transition metal catalysts were required.
• Enaminoate products were obtained with high versatility.

Conclusions:

• A novel, metal-free synthetic route for aminoarylation of alkynes has been established.
• The Smiles-Truce rearrangement is key to this C-N bond-forming transformation.
• The enaminoate products serve as valuable synthons for diverse heterocyclic compounds.