Biomaterial Database

Hypervalent Iodine Reagents Enable C(sp2)-H Amidation of (Hetero)arenes with Iminophenylacetic Acids. 2022

Yue Pan, and Zhengyi Liu, and Peng Zou, and Yali Chen, and Yiyun Chen

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.

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.

UI	MeSH Term	Description	Entries
D007202	Indicators and Reagents	Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)	Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D007211	Indoles	Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D007454	Iodides	Inorganic binary compounds of iodine or the I- ion.	Iodide
D007455	Iodine	A nonmetallic element of the halogen group that is represented by the atomic symbol I, atomic number 53, and atomic weight of 126.90. It is a nutritionally essential element, especially important in thyroid hormone synthesis. In solution, it has anti-infective properties and is used topically.	Iodine-127,Iodine 127
D011758	Pyrroles	Azoles of one NITROGEN and two double bonds that have aromatic chemical properties.	Pyrrole
D013449	Sulfonamides	A group of compounds that contain the structure SO2NH2.	Sulfonamide,Sulfonamide Mixture,Sulfonamide Mixtures,Mixture, Sulfonamide,Mixtures, Sulfonamide