Functionalization of [2.2]paracyclophanes via a reductive sulfanylation reaction

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

doi:10.1021/acs.joc.0c02235

Functionalization of [2.2]paracyclophanes via a reductive sulfanylation reaction

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

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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 language	English
Pages (from-to)	507-514
Number of pages	8
Journal	The Journal of Organic Chemistry
Volume	86
Issue number	1
Early online date	15 Dec 2020
DOIs	https://doi.org/10.1021/acs.joc.0c02235
Publication status	Published - 1 Jan 2021

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https://pubs.acs.org/doi/10.1021/acs.joc.0c02235

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AU - Deschamps, Damien

AU - Lohier, Jean-François

AU - Richards, Christopher J.

AU - Gaumont, Annie-Claude

AU - Perrio, Stéphane

PY - 2021/1/1

Y1 - 2021/1/1

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AB - 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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EP - 514

JO - The Journal of Organic Chemistry

JF - The Journal of Organic Chemistry

IS - 1

ER -

Functionalization of [2.2]paracyclophanes via a reductive sulfanylation reaction

Abstract

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