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Updated: Jul 13, 2026

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Synthesis of Allenyl Sulfur Compounds via Copper-Catalyzed Formal [3,3]-Rearrangement of O-Propargyl Carbamothioates
Cheng Wang1, Chun Wang1, Li-Jie Cheng1
1State Key Laboratory of Chemo and Biosensing, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, China.
Abstract:
A base-free, copper-catalyzed formal [3,3]-rearrangement of O-propargyl carbamothioates has been developed, enabling the efficient synthesis of allenyl sulfur compounds in high yields with excellent regioselectivity. The method accommodates various O-propargyl carbamothioates, including those bearing primary, secondary, and tertiary alkyl substituents, and tolerates a broad range of functional groups. Mechanistic investigations suggest that the rearrangement proceeds via a pseudointramolecular nucleophilic attack of a sulfur anion on a copper-allenylidene intermediate.
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