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Paper | Special issue | Vol 86, No. 1, 2012, pp.255-266
Published online, 8th May, 2012
DOI: 10.3987/COM-12-S(N)6
C-H Arylation of 3-Substituted Thiophene with Regioselective Deprotonation by TMPMgCl·LiCl and Transition Metal Catalyzed Cross Coupling

Shota Tanaka, Shunsuke Tamba, Atsushi Sugie, and Atsunori Mori*

*Department of Chemical Science and Engineering, Faculty of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan


The reaction of 3-hexylthiophene with Knochel-Hauser base (TMPMgClLiCl) induced the metalation at the 5-position of the thiophene ring selectively. Following addition of several aryl halides in the presence of a nickel or palladium catalyst afforded regioselectively arylated thiophene in good to excellent yields.