Owing to the pervasiveness of hydroxyl groups in natural isolates, alcohol derivatives are alluring directing groups. Herein, an alcohol-anchored sulfamate ester guides the xanthylation and alkylation of aliphatic C(3)–H bonds. The disclosed methods rely on light and photoredox mediated processes to generate sulfamyl radicals. These sulfamyl radicals template, otherwise rare, 1,6-hydrogen-atom transfer (HAT) processes via seven-membered ring transition states to enable C(3)–H functionalization. The developed reactions proceed with predictable selectivity offering a valuable tool for late stage modification of pharmacologically relevant small molecules.<br/>

Sulfamate esters guide C(3)–H functionalization of alkanes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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