Deprotonative Metalation of Chlorothiophene with Grignard Reagents and Catalytic cis-2,6-Dimethylpiperidine under Mild Conditions
2013; Thieme Medical Publishers (Germany); Volume: 24; Issue: 09 Linguagem: Inglês
10.1055/s-0033-1338385
ISSN1437-2096
AutoresAtsunori Mori, Shunsuke Tamba, Kenji Ide, Keisuke Shono, Atsushi Sugie,
Tópico(s)Inorganic Chemistry and Materials
ResumoDeprotonative metalation of chlorothiophene takes place with a catalytic amount of cis -2,6-dimethylpiperidine (DMP) and an alkyl Grignard reagent at room temperature for three hours to give the corresponding thienyl Grignard reagent. Polymerization leading to head-to-tail-type poly(3-substituted thiophene) with the thus metalated chlorothiophene proceeds in the presence of a nickel catalyst bearing an N -heterocyclic carbene (NHC) ligand. Palladium-catalyzed cross-coupling reaction with aryl bromides also gives arylated thiophenes in good to excellent yields while the C–Cl bond remains intact.
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