Protecting-Group-Free Synthesis of Novel Symmetrical and Unsymmetrical Diynes Dialdehyde via Copper-Catalyzed Glaser–Hay reaction: An Experimental and Computational Study
نویسندگان
1 Institute of Earth and Universe Sciences, University of Batna 2, 05001 Batna, Algeria
2 Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Vanak, Tehran, 1993893973, Iran
3 Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Vanak, Tehran, 1993893973, Iran
4 Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Vanak, Tehran, 1993893973, Iran
5 Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Vanak, Tehran, 1993893973, Iran
6 Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Vanak, Tehran, 1993893973, Iran
7 Department of Organic Chemistry, Faculty of Chemistry, Alzahra University, Vanak, Tehran, 1993893973, Iran
doi
10.48309/chemm.2025.479447.1828چکیده
We developed a straightforward Glaser–Hay reaction route for CuCl and 2-aminopyridine-mediated coupling of terminal alkynes. Our protecting-group-free synthetic route provides a high yield of symmetrical diynes, particularly those containing dialdehyde groups. Furthermore, symmetric diketone-containing diynes, aromatic diynes, and unsymmetric diyne containing an aldehyde or ketone functional group have been synthesized. The final products were characterized by FT-IR, HRMS, 1H-NMR, 13C-NMR, and DEPT spectroscopy. The results of this study demonstrate the versatility and utility of this methodology for synthesizing a broad range of diynes with various functional groups as a potential crosslinker for the preparation of polymers, macrocycles, and hydrogels and as potential ligands. In a further dimension of our study, we expanded our study by incorporating a theoretical study. This entailed employing Density Functional Theory (DFT) calculations to predict the reactivity of the resultant products. These calculations shed light on the descriptor reactivity and dual descriptor (DD) properties of the synthesized products, providing insights into their behavior, particularly concerning nucleophilic and electrophilic reactions.
