2020年7月2日
Tandem Oxidative Ring Expansion for Synthesis of Dibenzocyclooctaphenanthrenes
Organic Letters
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- ,
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- 巻
- 22
- 号
- 13
- 開始ページ
- 5121
- 終了ページ
- 5125
- 記述言語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/acs.orglett.0c01725
- 出版者・発行元
- American Chemical Society ({ACS})
A novel tandem single-electron oxidative ring expansion reaction has been developed for the construction of the saddle-shaped polycyclic arenes fused with cyclooctatetraene, that is, dibenzo[3,4:7,8]cycloocta[1,2-l]phenanthrenes (dbCOTPs). The combination of Cu(OTf)2 catalyst with DDQ triggered the selective oxidation of o-biphenyl-tethered methylenecirculenes fused with a seven-membered ring, giving rise to the formation of the corresponding eight-membered ring fused dbCOTPs. The present tandem ring expansion of a seven- to an eight-membered ring takes place via the selective single-electron oxidation of the benzylidene moiety, intramolecular spirocyclization, and 1,2-aryl migration sequence.
- リンク情報
- ID情報
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- DOI : 10.1021/acs.orglett.0c01725
- ISSN : 1523-7060
- eISSN : 1523-7052
- ORCIDのPut Code : 75863540
- PubMed ID : 32551687
- SCOPUS ID : 85087528941