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Issue 4, 2019
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A one-pot metal-free protocol for the synthesis of chalcogenated furans from 1,4-enediones and thiols

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Abstract

Transition-metal-free synthesis of chalcogenated furans through the sequential thiol-Michael/Paal–Knorr reaction of 1,4-enediones in the presence of a catalytic amount of p-toluenesulfonic acid has been developed. The present one-pot strategy involves the thiol Michael addition to 1,4-enediones in an anti-Markovnikov fashion with the formation of a new C–S bond, followed by intramolecular dehydrative annulation in the presence of cat. TsOH delivering fully substituted furans in good to excellent yields (50–99%). The reaction is compatible with a wide range of substrates and also capable of multi-gram scale synthesis of chalcogenated furans.

Graphical abstract: A one-pot metal-free protocol for the synthesis of chalcogenated furans from 1,4-enediones and thiols

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Publication details

The article was received on 07 Dec 2018, accepted on 03 Jan 2019 and first published on 03 Jan 2019


Article type: Paper
DOI: 10.1039/C8OB03051K
Citation: Org. Biomol. Chem., 2019,17, 982-991

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    A one-pot metal-free protocol for the synthesis of chalcogenated furans from 1,4-enediones and thiols

    V. Rajeshkumar, C. Neelamegam and S. Anandan, Org. Biomol. Chem., 2019, 17, 982
    DOI: 10.1039/C8OB03051K

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