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Synfacts 2011(7): 0730-0730  
DOI: 10.1055/s-0030-1260617
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Unexpected Increase in Antiaromaticity through Heteroannulation of Borole

Contributor(s): Timothy M. Swager, Jason R. Cox
A. Iida, S. Yamaguchi*
Nagoya University and Japan Science and Technology Agency, CREST, Nagoya, Japan
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Publication History

Publication Date:
17 June 2011 (online)

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Significance

The authors describe the syntheses and properties of thiophene-fused borole compounds. The synthesis of compound 2 features an intramolecular nucleophilic substitution of the boron center via lithiation of the bromo­thiophene ring. Compounds 3 and 4 result from 5-endo-dig cyclization. The resulting compounds exhibit high antiaromaticity.