2021年3月22日
A Robust Porphyrin‐Stabilized Triplet Carbon Diradical
Angewandte Chemie International Edition
- 巻
- 60
- 号
- 13
- 開始ページ
- 7002
- 終了ページ
- 7006
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1002/anie.202015356
- 出版者・発行元
- Wiley
The synthesis of robust high-spin carbon radicals is an important topic in organic chemistry. Toward this end, several porphyrin-stabilized radicals have been systematically explored. A singly naphthalene-fused porphyrin radical was synthesized by a reaction sequence consisting of a Suzuki-Miyaura coupling of beta-borylated porphyrin with 2-bromobenzaldehyde, addition of mesityl Grignard reagent, intramolecular Friedel-Crafts alkylation, and final oxidation with DDQ or tBuOK/O-2. This strategy was also used to synthesize doubly naphthalene-fused porphyrins and syn- and anti-fused-anthracene-bridged porphyrin dimers. While singly naphthalene-fused porphyrin radical has been shown to be a stable monoradical, doubly naphthalene-fused porphyrins and anti-fused-anthracene-bridged porphyrin dimers have been shown to be closed-shell molecules. Finally, the syn-dimer was characterized as a surprisingly stable radical (t(1/2)=28 days under ambient air and at 80 degrees C) that is storable for more than several months, despite its high-spin triplet ground-state carbon diradical.
- リンク情報
-
- DOI
- https://doi.org/10.1002/anie.202015356
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000621037100001&DestApp=WOS_CPL
- URL
- https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202015356
- URL
- https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.202015356
- ID情報
-
- DOI : 10.1002/anie.202015356
- ISSN : 1433-7851
- eISSN : 1521-3773
- ORCIDのPut Code : 115597338
- Web of Science ID : WOS:000621037100001