高价碘试剂促进碘苯乙酸与（杂）芳基的 C(sp)-H 酰胺化反应。
Hypervalent Iodine Reagents Enable C(sp)-H Amidation of (Hetero)arenes with Iminophenylacetic Acids.
机构信息
State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 China.
Department of Chemistry, Shanghai University, 99 Shangda Road, Shanghai 200444 China.
出版信息
Org Lett. 2022 Sep 16;24(36):6681-6685. doi: 10.1021/acs.orglett.2c02751. Epub 2022 Aug 31.
Sulfonamide-containing (hetero)arenes are widely present in bioactive molecules. Here, we report the sulfonamidyl (hetero)arenes synthesis by the C(sp)-H amidation from bench-stable amidyl-iminophenylacetic acids. The hypervalent iodine reagents covalently activated iminophenylacetic acids for the facile sulfonamidyl radical generation under mild photocatalytic oxidative conditions. Diversified indoles, pyrroles, imidazopyridines, and fused arenes underwent the C(sp)-H amidation with excellent chemoselectivity and regioselectivity. This reaction performs well under neutral aqueous conditions with potential biological applications.
含磺酰胺的（杂）芳基广泛存在于生物活性分子中。在这里，我们报道了通过稳定的氨甲酰基亚胺基苯乙酸的 C(sp)-H 酰胺化反应来合成磺酰胺基（杂）芳基。高价碘试剂通过共价键活化亚胺基苯乙酸，在温和的光催化氧化条件下，易于生成磺酰胺基自由基。多种吲哚、吡咯、咪唑并吡啶和稠环芳烃在中性水条件下具有潜在的生物应用价值，通过 C(sp)-H 酰胺化反应，以优异的化学选择性和区域选择性得到了目标产物。
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