Functionalization of [2.2]paracyclophanes via a reductive sulfanylation reaction

Damien Deschamps, Jean-François Lohier, Christopher J. Richards, Annie-Claude Gaumont, Stéphane Perrio

Research output: Contribution to journalArticle

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)507-514
Number of pages8
JournalThe Journal of Organic Chemistry
Volume86
Issue number1
Early online date15 Dec 2020
DOIs
Publication statusPublished - 1 Jan 2021

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