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Hypervalent Iodine Reagents Enable C(sp2)-H Amidation of (Hetero)arenes with Iminophenylacetic Acids.

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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… Click to show full 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.

Keywords: hypervalent iodine; iodine reagents; iminophenylacetic acids; hetero arenes; sp2 amidation

Journal Title: Organic letters
Year Published: 2022

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