ChemInform Abstract: Deprotonative Metalation of Chlorothiophene with Grignard Reagents and Catalytic cis‐2,6‐Dimethylpiperidine under Mild Conditions.

Abstract

Deprotonative Metalation of Chlorothiophene with Grignard Reagents and Catalytic cis-2,6-Dimethylpiperidine under Mild Conditions. -The title process affords thienyl-Grignard reagents which undergo Pd-catalyzed coupling with aryl bromides to form 5-substituted products with the C-Cl bond remaining intact. An additional coupling allows the synthesis of 2,5-diarylated thiophenes such as (VI), a partial structure of MK-2 dye. -(TAMBA, S.; IDE, K.; SHONO, K.; SUGIE, A.; MORI*, A.; Synlett 24 (2013) 9, 1133-1136, http://dx.doi.org/10.1055/s-0032-1338385 ; Dep. Chem. Sci. Eng., Fac. Eng., Kobe Univ., Nada, Kobe 657, Japan; Eng.) -Mais 39-102