Selective and Divergent Synthesis of Naphthalene‐ and Phenanthrene‐Fused Azahelicenes by Turning Rearrangement On or Off

• 資料種別: 記事
• タイトル: Selective and Divergent Synthesis of Naphthalene‐ and Phenanthrene‐Fused Azahelicenes by Turning Rearrangement On or Off
• 著者・編者: 前田, 千尋; Maeda, Chihiro
• 著者標目: 前田, 千尋; Maeda, Chihiro
• 出版年月日等: 2025-01
• 出版年（W3CDTF）: 2025
• 並列タイトル等: Selective and Divergent Synthesis of Naphthalene‐ and Phenanthrene‐Fused Azahelicenes by Turning Rearrangement On or Off
• タイトル（掲載誌）: Chemistry – A European Journal
• ISSN（掲載誌）: ISSN : 0947-6539; ISSN : 1521-3765
• 対象利用者: 一般
• 一般注記: 出版タイプ： NA; <jats:title>Abstract</jats:title><jats:p>The Scholl reaction has been used to synthesize a variety of polycyclic aromatic hydrocarbons, where 1,2‐aryl shifts have sometimes occurred to yield unique rearrangement products. However, such 1,2‐aryl shifts are often uncontrollable, and the selective and divergent synthesis with or without rearrangement is desired. Here, we achieved the control of the rearrangement in the Scholl reaction of carbazoles by changing the <jats:italic>N</jats:italic>‐substituents. The Scholl reaction of 3,6‐bis{2‐(2‐naphthyl)phenyl}carbazoles and 3,6‐bis{2‐(9‐phenanthrenyl)phenyl}carbazoles with an <jats:italic>N</jats:italic>‐benzyl group gave multiple azahelicenes via double rearrangement, while those with an <jats:italic>N</jats:italic>‐benzoyl group gave aza[9]helicene and quadruple [4]helicene in the former and latter cases, respectively. The reaction mechanisms on the divergent reaction pathways were investigated by DFT calculations, which well supported the experimental results.</jats:p>; identifier:oai:t2r2.star.titech.ac.jp:50736649
• 関連情報（DOI）: 10.1002/chem.202404325; https://doi.org/10.1002/chem.202404325
• 連携機関・データベース: 国立情報学研究所 : 学術機関リポジトリデータベース（IRDB）（機関リポジトリ）; https://irdb.nii.ac.jp
• 提供元機関・データベース: 東京科学大学 : 東京科学大学リサーチリポジトリ(T2R2)