Enantioselective Synthesis of Axially Chiral 1,8-Diarylnaphthalenes by Rh-Catalyzed [2 + 2 + 2] Cycloaddition and Evaluation of Their Chiroptical Properties
Intermolecular [2 + 2 + 2] cycloaddition of 1-alkynyl-8-arylnaphthalenes with 1,6-diynes proceeded in the presence of Rh-chiral BINAP derivative catalysts to give axially chiral 1,8-diarylnaphthalenes in excellent yields along with up to perfect enantioselectivity. As the aryl moiety, we could introduce 1-pyrenyl and (dibenzo)carbazolyl groups in addition to substituted phenyl ones. 1-Aryl-8-(1-pyrenyl)naphthalenes exhibited high fluorescence quantum yields (up to Φ = 0.89) and circularly polarized luminescence (CPL) properties (|<i>g</i><sub>lum</sub>| = up to 1.6 × 10<sup>-3</sup>).
Authors
- Hiroki Nikawa (ORCID: https://orcid.org/0000-0002-4883-5723)
- Mamoru Ito (ORCID: https://orcid.org/0000-0002-9020-1337)
- Tohru Taniguchi (ORCID: https://orcid.org/0000-0002-4965-7383)
- Takanori Shibata (ORCID: https://orcid.org/0000-0003-4436-8264)
- Kenji Monde (ORCID: https://orcid.org/0000-0002-1424-1054)
- Ema Kadosaka
Institutions
- Waseda University (JP)
- Hokkaido University (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-18
- DOI
- https://doi.org/10.1021/acs.orglett.5c01037
- Citations
- 2
- Primary Topic
- Axial and Atropisomeric Chirality Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Waseda University