Iridium-Catalyzed Synthesis of Chiral 1,2,3-Triazoles Units and Precise Construction of Stereocontrolled Oligomers

• Published in: Molecules (Basel, Switzerland) Vol. 28; no. 9; p. 3726
• Main Authors: Zhang, Xueyan, Yu, Tian, Ding, Shengtao
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 26.04.2023; MDPI
• Subjects: Azide; Catalysis; chiral triazole; Circular dichroism; Construction; Cycloaddition; Dichroism; Gases industry; iridium catalysis; Mass spectrometry; Mass spectroscopy; NMR; Nuclear magnetic resonance; Oligomers; optical property; precise construction; Regioselectivity; Size exclusion chromatography; stereoregularity; Triazoles; United States; China; stereoregularity; chiral triazole; optical property; iridium catalysis; precise construction
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules28093726

Iridium-catalyzed azide-thioalkyne cycloaddition reaction (IrAAC) has proved to be a powerful tool for the synthesis of fully substituted 1,2,3-triazole compounds with exclusive regioselectivity. Here we report its successful use in the precise construction of stereocontrolled oligomers that have great potential in diverse applications. Starting with the azide derived from L-prolinol and different functionalized thioalkynes, chiral 1,2,3-triazole units were fabricated with high efficiency under the IrAAC condition, which were further assembled into stereocontrolled oligotriazoles through metal-free exponential growth strategies. The structure and uniformity of these oligomers were well identified by H NMR, size-exclusion chromatography, and mass spectrometry, the stereoregularity of which were studied through circular dichroism and circular polarized luminescence analysis.