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Iron-Catalyzed Sulfonylthiocyanation of α,β-Unsaturated Amides/Esters via the Insertion of Sulfur Dioxide.

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An iron-catalyzed four-component sulfonylthiocyanation between α,β-unsaturated amides/esters, TMSNCS, aryldiazonium tetrafluoroborates, and sulfur dioxide (from SOgen) is demonstrated. This protocol is characterized by mild reaction conditions, good functional group compatibility, broad… Click to show full abstract

An iron-catalyzed four-component sulfonylthiocyanation between α,β-unsaturated amides/esters, TMSNCS, aryldiazonium tetrafluoroborates, and sulfur dioxide (from SOgen) is demonstrated. This protocol is characterized by mild reaction conditions, good functional group compatibility, broad substrate scope, and good to excellent yields, providing a feasible method for the preparation of β-thiocyanated sulfone compounds. The preliminary mechanism investigation shows that a radical pathway may be involved in the process.

Keywords: sulfonylthiocyanation unsaturated; sulfur dioxide; iron catalyzed; unsaturated amides; amides esters

Journal Title: Organic letters
Year Published: 2022

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