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Aromatic Metamorphosis of Thiophenes by Means of Desulfurative Dilithiation
Atsushi Kaga1, Hirokazu Iida2, Shun Tsuchiya1
1Department of Chemistry, Graduate School of Science, Sakyo-ku, Kyoto, 606-8502, Japan.
Abstract:
A new mode of aromatic metamorphosis has been developed, which allows thiophenes and their benzo-fused derivatives to be converted to a variety of exotic heteroles. This transformation involves 1) the efficient generation of key 1,4-dianions by means of desulfurative dilithiation with lithium powder and 2) the subsequent trapping of the dianions with heteroatom electrophiles in a one-pot manner. Via the desulfurative dilithiation, the sulfur atoms of thiophenes are replaced also with a carbon-carbon double bond or a 1,2-phenylene for the construction of benzene rings.
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