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Updated: Feb 19, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Sulfamate Esters Guide Selective Radical-Mediated Chlorination of Aliphatic C-H Bonds
Melanie A Short1, J Miles Blackburn1, Jennifer L Roizen1
1Duke University, Department of Chemistry, Box 90346, Durham, NC, 27708-0354, USA.
Abstract:
Masked alcohols are particularly appealing as directing groups because of the ubiquity of hydroxy groups in organic small molecules. Herein, we disclose a general strategy for aliphatic γ-C(sp3 )-H functionalization guided by a masked alcohol. Specifically, we determine that sulfamate ester derived nitrogen-centered radicals mediate 1,6-hydrogen-atom transfer (HAT) processes to guide γ-C(sp3 )-H chlorination. This reaction proceeds through a light-initiated radical chain-propagation process and is capable of installing chlorine atoms at primary, secondary, and tertiary centers.
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