Shibata Takanori, Nikawa Hinako, Kadosaka Ema, Ito Mamoru, Taniguchi Tohru, Monde Kenji
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku, Tokyo 169-8555, Japan.
Frontier Research Center for Advanced Material and Life Science, Faculty of Advanced Life Science, Hokkaido University, Sapporo 001-0021, Japan.
Org Lett. 2025 May 2;27(17):4524-4528. doi: 10.1021/acs.orglett.5c01037. Epub 2025 Apr 18.
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 (|| = up to 1.6 × 10).
1-炔基-8-芳基萘与1,6-二炔在铑-手性联萘酚衍生物催化剂存在下进行分子间[2 + 2 + 2]环加成反应，以优异的产率和高达完美的对映选择性得到轴向手性1,8-二芳基萘。作为芳基部分，除了取代苯基外，我们还可以引入1-芘基和（二苯并）咔唑基。1-芳基-8-（1-芘基）萘表现出高荧光量子产率（高达Φ = 0.89）和圆偏振发光（CPL）性质（||高达1.6×10）。
