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Atom-Economical Thiocyanation-Amination of Alkynes with <i>N</i>-Thiocyanato-Dibenzenesulfonimide

Haopeng Wu, Chukai Shao, Di Wu, Liang Jiang, Hongquan Yin, Fu‐Xue Chen

2021The Journal of Organic Chemistry25 citationsDOI

Abstract

A highly regioselective protocol for intermolecular thiocyanation-amination of alkynes by N-thiocyano-dibenzenesulfonimide (NTSI) as the SCN and nitrogen sources has been developed. A C–S bond and C–N bond are simultaneously constructed in only one step. The reaction under simple mild conditions features a broad substrate scope, atom economy, high yields (up to 94%), and excellent functional group tolerance.

Topics & Concepts

ChemistryAminationRegioselectivityAtom economyFunctional groupNitrogen atomSubstrate (aquarium)Intermolecular forceMedicinal chemistryReaction conditionsCombinatorial chemistryAlkyneOrganic chemistryCatalysisMoleculeGroup (periodic table)OceanographyPolymerGeologySulfur-Based Synthesis TechniquesSynthesis and Catalytic ReactionsChemical Synthesis and Reactions
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