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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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Supplementary files

Article information


Submitted
17 Jun 2019
Accepted
12 Jul 2019
First published
13 Jul 2019

Org. Biomol. Chem., 2019,17, 7315-7319
Article type
Communication

(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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