ヨウ素および(ポリ)ヨウ化水素を用いた多重結合活性化による環構造構築反応

概要

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Molecular iodine and hydrogen iodide are known to promote cationic species by addition to multiple bonds. The cationic species can form C-C, C-O, and C-N bonds. The development of new reactions using iodine and hydrogen iodide is playing an important role in synthetic organic chemistry. Herein we report our investigation of the carbon-carbon bond formation of conjugated compounds with iodine and hydrogen (poly)iodide using activation of the multiple bonds. Various cyclic compounds such as naphthalenes, iodobenzenes, quinolines, and dihydroquinolines were formed from aryldienes, dienynes, and enamines under thermal and photochemical conditions. We also found a unique cyclization reaction including a 1,2-sulfonyl migration using hydrogen polyiodide. The reactions specifically proceeded by the characteristic nature of the iodine element and the oxidative and reductive properties of iodine and hydrogen iodide, which were also used efficiently to yield various compounds in combination with the sulfur moiety attached to reaction materials.
社団法人有機合成化学協会の論文
2011-02-01