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Gold-Catalyzed Intermolecular Alkyne Insertion into the N-S Bond in Sulfenamides.

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Gold-catalyzed reactions between sulfenamides and terminal alkynes proceeded via cis-insertion of alkynes into the N-S bond in sulfenamides, affording the corresponding β-sulfenylenamines in yields up to 90%. Mechanistic studies revealed… Click to show full abstract

Gold-catalyzed reactions between sulfenamides and terminal alkynes proceeded via cis-insertion of alkynes into the N-S bond in sulfenamides, affording the corresponding β-sulfenylenamines in yields up to 90%. Mechanistic studies revealed that the reactions proceeded via nucleophilic attack of the sulfenamide nitrogen atom on the π-activated alkyne, followed by tosylate-assisted intermolecular transfer of the sulfenyl group.

Keywords: bond sulfenamides; catalyzed intermolecular; insertion; gold catalyzed; intermolecular alkyne

Journal Title: Organic letters
Year Published: 2022

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