Functionalization of [2.2]paracyclophanes via a reductive sulfanylation reaction

Deschamps, Damien, Lohier, Jean-François, Richards, Christopher J., Gaumont, Annie-Claude and Perrio, Stéphane (2021) Functionalization of [2.2]paracyclophanes via a reductive sulfanylation reaction. The Journal of Organic Chemistry, 86 (1). pp. 507-514. ISSN 0022-3263

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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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
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Depositing User: LivePure Connector
Date Deposited: 09 Mar 2021 00:41
Last Modified: 30 Sep 2021 16:13
DOI: 10.1021/acs.joc.0c02235

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