Year: 2025
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide Iodonium salts have shown great potential as metal-free reagents in various transformations, offering a promising alternative to transition-metal-catalyzed arene amination. Herein, we report the design and synthesis of chromone-based iodonium salts (CMISs) and demonstrate their efficiency in selective chromone amination. Unlike the conventional ligand exchange/coupling pathway, mechanistic studies reveal a unique amination pathway specific to the chromone scaffold, in which the aryliodonium unit simultaneously facilitates N -Michael addition and the formation of a newfound chromone-derived strained alkyne intermediate, leading to mechanistic competition while directing product configuration. By further modulating the basicity and steric hindrance of amines, three distinct classes of aminated products (( Z )-2-(aminomethylene)benzofuranones, β-aminochromones and α-aminochromones) were accessed.
Source: JACS Au
Authors: Shuoshuo Zhang, Zhifang Yang, Haofeng Shi, Xuemin Li, Hui Zhao, Yunfei Du
Institution: Tianjin University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $3,500
Award: 高价碘化物/DMSO介导下含硫杂环化合物的合成新方法研究
OpenAlex ID: W4415926713