Construction of Condensed Polycyclic Aromatic Frameworks through Intramolecular Cycloaddition Reactions Involving Arynes Bearing an Internal Alkyne Moiety
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- Suguru Yoshida
- Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering Tokyo Medical and Dental University (TMDU) 2-3-10 Kanda-Surugadai, Chiyoda-ku Tokyo 101-0062 Japan
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- Keita Shimizu
- Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering Tokyo Medical and Dental University (TMDU) 2-3-10 Kanda-Surugadai, Chiyoda-ku Tokyo 101-0062 Japan
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- Keisuke Uchida
- Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering Tokyo Medical and Dental University (TMDU) 2-3-10 Kanda-Surugadai, Chiyoda-ku Tokyo 101-0062 Japan
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- Yuki Hazama
- Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering Tokyo Medical and Dental University (TMDU) 2-3-10 Kanda-Surugadai, Chiyoda-ku Tokyo 101-0062 Japan
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- Kazunobu Igawa
- Institute for Materials Chemistry and Engineering Kyushu University 6-1 Kasuga-koen, Kasuga Fukuoka 816-8580 Japan
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- Katsuhiko Tomooka
- Institute for Materials Chemistry and Engineering Kyushu University 6-1 Kasuga-koen, Kasuga Fukuoka 816-8580 Japan
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- Takamitsu Hosoya
- Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering Tokyo Medical and Dental University (TMDU) 2-3-10 Kanda-Surugadai, Chiyoda-ku Tokyo 101-0062 Japan
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説明
<jats:title>Abstract</jats:title><jats:p>Facile synthetic methods for condensed polycyclic aromatic compounds via aryne intermediates are reported. The generation of arynes bearing a (3‐arylpropargyl)oxy group from the corresponding <jats:italic>o</jats:italic>‐iodoaryl triflate‐type precursors efficiently afforded arene‐fused oxaacenaphthene derivatives, which were formed through intramolecular [2+4] cycloaddition. Extending the method to the generation of arynes bearing a 1,3‐diyne moiety led to a continuous generation of naphthalyne intermediate through the hexadehydro Diels–Alder reaction involving the aryne triple bond. This novel type of aryne‐relay chemistry enabled the synthesis of a unique aminoarylated oxaacenaphthene derivative and highly ring‐fused anthracene derivatives.</jats:p>
収録刊行物
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- Chemistry – A European Journal
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Chemistry – A European Journal 23 (61), 15332-15335, 2017-10-10
Wiley