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Short Paper | Special issue | Vol 90, No. 1, 2015, pp.681-689
Published online, 18th June, 2014
DOI: 10.3987/COM-14-S(K)34
Generation and Reactions of Heteroaromatic Arynes Using Hypervalent Iodine Compounds

Keisuke Gondo, Juzo Oyamada, and Tsugio Kitamura*

*Department of Chemistry and Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi, Saga, Japan

Abstract

The heterocyclic aryne precursors, (phenyl)[1-phenyl-6-(trimethylsilyl)benzotriazol-5-yl]iodonium triflate and [3-ethoxycarbonyl-6-(trimethylsilyl)indazol-5-yl](phenyl)iodonium triflate, were prepared from the cycloadducts of 4,5-bis(trimethylsilyl)benzyne generated from (phenyl)[2,4,5-tris(trimethylsilyl)phenyl]iodonium triflate. These precursors provide the corresponding arynes, 1-phenyl-5,6-didehydrobenzotriazole and 3-ethoxycarbonyl-5,6-didehydroindazole, to give the corresponding polycyclic heteroaromatic compounds in good to high yields.