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Issue 31, 2019
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(Z)-Tetrahydrothiophene and (Z)-tetrahydrothiopyran synthesis through nucleophilic substitution and intramolecular cycloaddition of alkynyl halides and EtOCS2K

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Abstract

This protocol provides a novel, environmentally friendly and simple method for the synthesis of (Z)-tetrahydrothiophene derivatives using the nucleophilic thiyl radical intramolecular cycloaddition cascade process to construct C–S bonds under transition-metal-free conditions. This transformation process offers a broad substrate scope, good functional group tolerance, and excellent stereoselectivity (Z/E ratios up to 99/1). Moreover, the process uses odourless, stable and cheap EtOCS2K as the sulfur source.

Graphical abstract: (Z)-Tetrahydrothiophene and (Z)-tetrahydrothiopyran synthesis through nucleophilic substitution and intramolecular cycloaddition of alkynyl halides and EtOCS2K

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Publication details

The article was received on 17 Jun 2019, accepted on 12 Jul 2019 and first published on 13 Jul 2019


Article type: Communication
DOI: 10.1039/C9OB01370A
Org. Biomol. Chem., 2019,17, 7315-7319

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    (Z)-Tetrahydrothiophene and (Z)-tetrahydrothiopyran synthesis through nucleophilic substitution and intramolecular cycloaddition of alkynyl halides and EtOCS2K

    X. Luo, Y. Li, X. Chen, Z. Song, J. Liang, C. Liao, Z. Zhu and L. Chen, Org. Biomol. Chem., 2019, 17, 7315
    DOI: 10.1039/C9OB01370A

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