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Magnesium Bisamide-Mediated Halogen Dance of Bromothiophenes
Yoshiki Yamane1, Kazuhiro Sunahara1, Kentaro Okano1
1Department of Chemical Science and Engineering , Kobe University , 1-1 Rokkodai, Nada , Kobe 657-8501 , Japan.
Abstract:
A magnesium bisamide-mediated halogen dance of bromothiophenes is described. The thienylmagnesium species generated in situ is more stable than the corresponding thienyllithium species, which was applied to trap the transient anion species with several electrophiles, such as allyl iodide, phenyl isocyanate, and tributylstannyl chloride. The utility of the magnesium bisamide-mediated halogen dance is useful in the concise synthesis of a medicinally advantageous compound via a one-pot, ester-directed halogen dance/Negishi cross coupling.
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