Morlacci Valerio, Aschi Massimiliano, Chiarini Marco, Momoli Caterina, Palombi Laura, Arcadi Antonio
Dipartimento di Scienze Fisiche e Chimiche, Università Degli Studi Dell'Aquila, Via Vetoio, 67100 Coppito, Italy.
Dipartimento di Bioscienze e Tecnologie Agroalimentari e Ambientali, Università Degli Studi di Teramo, Via R. Balzarini, 64100 Teramo, Italy.
Molecules. 2024 Aug 4;29(15):3693. doi: 10.3390/molecules29153693.
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.
报道了布朗斯特酸催化/介导的2-炔基苯胺反应。虽然这些有价值的结构单元的金属催化反应已导致建立了用于选择性、多样化导向合成重要杂环衍生物的稳健方案，但我们在此展示了无金属条件下另一种方法的实际优势。我们对影响2-炔基苯胺的布朗斯特酸催化/介导反应中产物选择性的关键因素进行的研究表明，通过简单选择合适的反应条件，不同的反应途径可导向形成多种有价值的产物。已通过密度泛函理论（DFT）计算探索了化学和区域选择性切换的起源。
