Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 17, Issue 4, Pages 982-991Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob03051k
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Funding
- Department of Science and Technology (DST), New Delhi, India under a DST-INSPIRE [DST/INSPIRE/04/2016/000295]
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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.
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