Hypervalent Iodine Reagents Enable C(sp2)-H Amidation of (Hetero)arenes with Iminophenylacetic Acids
Yue Pan1,2, Zhengyi Liu1, Peng Zou1
1State 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.
Abstract:
Sulfonamide-containing (hetero)arenes are widely present in bioactive molecules. Here, we report the sulfonamidyl (hetero)arenes synthesis by the C(sp2)-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(sp2)-H amidation with excellent chemoselectivity and regioselectivity. This reaction performs well under neutral aqueous conditions with potential biological applications.
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