Synthesis of N-arylated sultams: Palladium- and copper-catalyzed cross coupling of aryl halides with 1,4-butane and 1,3-propanesultams

Tetrahedron Letters

Volumn 45, Issue 16, 2004, Pages 3305-3307

  Steinhuebel, Dietrich ^a   Palucki, Michael ^a   Askin, David ^a   Dolling, Ulf ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Palladium; Sultam

Indexed keywords

BUTANE; COPPER; HALIDE; LIGAND; PALLADIUM; PROPANE;

ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; CROSS COUPLING REACTION; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 1642603915     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.081     Document Type: Article

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16. In the case of 2-(3-bromophenyl)-1,3-dioxalane the coupling reaction with 1,4-butane sultam was not clean. Attempted coupling of 2-bromo anisole with 1,4-butane sultam resulted in low conversion. In a single experiment we isolated ∼30-40% of the coupling product of 1,4-butane sultam with 3-bromoanisole.
17. Under similar conditions, 1,4-butane sultam and phenyl iodide afforded arylated product but the reaction suffers from slow conversion and formation of unidentified products.
18. 2/EtOAc) to afford the product as a white solid (1. 12 g, 89%).