Product Selectivity Control in the Brønsted Acid-Mediated Reactions with 2-Alkynylanilines

Molecules. 2024 Aug 4;29(15):3693. doi: 10.3390/molecules29153693.

Abstract

Brønsted acid-catalysed/mediated reactions of the 2-alkynylanilines are reported. While metal-catalysed reactions of these valuable building blocks have led to the establishment of robust protocols for the selective, diverse-oriented syntheses of significant heterocyclic derivatives, we here demonstrate the practical advantages of an alternative methodology under metal-free conditions. Our investigation into the key factors influencing the product selectivity in Brønsted acid-catalysed/mediated reactions of 2-alkynylanilines reveals that different reaction pathways can be directed towards the formation of diverse valuable products by simply choosing appropriate reaction conditions. The origins of chemo- and regioselectivity switching have been explored through Density Functional Theory (DFT) calculations.

Keywords: 2-alkynylanilines; DFT calculations; annulations; sequential reactions.

Grants and funding

This research received no external funding.