Aromatic Metamorphosis of Thiophenes by Means of Desulfurative Dilithiation |
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Authors: | Dr Atsushi Kaga Hirokazu Iida Shun Tsuchiya Hayate Saito Prof?Dr Koji Nakano Prof?Dr Hideki Yorimitsu |
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Institution: | 1. Department of Chemistry, Graduate School of Science, Sakyo-ku, Kyoto, 606-8502 Japan;2. Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo, 184–8588 Japan |
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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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Keywords: | desulfurization dianion heterole lithium metal thiophene |
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