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Updated: Nov 25, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Functionalization of [2.2]Paracyclophanes via a Reductive Sulfanylation Reaction
Damien Deschamps1, Jean-François Lohier1, Christopher J Richards2
1Normandie Univ, ENSICAEN, UNICAEN, CNRS, LCMT, 14000 Caen, France.
Abstract:
An expeditious route to planar chiral sulfur-based scaffolds has been achieved in two operational steps from cheap and commercial [2.2]paracyclophane hydrocarbon. The sulfur atom was introduced in a specific benzylic position of the [2.2]paracyclophane according to a reductive sulfanylation reaction, which proceeds under two complementary reaction conditions with either the BF3·OEt2/Et3SiH or TFA/BH3·THF combinations. The study was completed by the development of a highly efficient resolution approach by HPLC.
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