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Updated: Jul 23, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Dual Copper- and Aldehyde-Catalyzed Transient C-H Sulfonylation of Benzylamines
Joe I Higham1, Tsz-Kan Ma1, James A Bull1
1Department of Chemistry, Imperial College London, Molecular Sciences Research Hub, White City Campus, Wood Lane, London W12 0BZ, United Kingdom.
Abstract:
This study reports the first example of using a dual catalytic system with copper(II) acetate and 2-hydroxynicotinaldehyde to achieve transient C(sp2)-H sulfonylation of benzylamines with sulfinate salts via a dynamically formed imine directing group. Manganese(IV) oxide was identified as an effective oxidant and base. Computational density functional theory investigations suggest that the transient directing group lowers the energy barrier for an acetate-mediated, turnover-limiting C-H activation step and subsequent combination of the cupracycle with a RSO2 radical.
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