通过铑催化的[2 + 2 + 2]环加成反应对轴向手性1,8 - 二芳基萘进行对映选择性合成及其手性光学性质评估。
Enantioselective Synthesis of Axially Chiral 1,8-Diarylnaphthalenes by Rh-Catalyzed [2 + 2 + 2] Cycloaddition and Evaluation of Their Chiroptical Properties.
作者信息
Shibata Takanori, Nikawa Hinako, Kadosaka Ema, Ito Mamoru, Taniguchi Tohru, Monde Kenji
机构信息
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.
出版信息
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）。
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