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
- 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 β-borylated porphyrin with 2-bromobenzaldehyde, addition of mesityl Grignard reagent, intramolecular Friedel–Crafts alkylation, and final oxidation with DDQ or tBuOK/O2. 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 (t1/2=28 days under ambient air and at 80 °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
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/33393192
- URL
- https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.202015356
- URL
- https://onlinelibrary.wiley.com/doi/full-xml/10.1002/anie.202015356
- Scopus
- https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85101517739&origin=inward
- Scopus Citedby
- https://www.scopus.com/inward/citedby.uri?partnerID=HzOxMe3b&scp=85101517739&origin=inward
- ID情報
-
- DOI : 10.1002/anie.202015356
- ISSN : 1433-7851
- eISSN : 1521-3773
- PubMed ID : 33393192
- SCOPUS ID : 85101517739