Li Yuanming, Yagi Akiko, Itami Kenichiro
Institute of Transformative Bio-Molecules (WPI-ITbM) , Nagoya University , Chikusa , Nagoya 464-8602 , Japan . Email:
Graduate School of Science , Nagoya University , Chikusa , Nagoya 464-8602 , Japan.
Chem Sci. 2019 Apr 17;10(21):5470-5475. doi: 10.1039/c9sc00334g. eCollection 2019 Jun 7.
The synthesis of sterically hindered phenanthrenes acid-catalyzed bisannulation reaction is described. Treatment of 1,4-benzenediacetaldehyde with terminal aryl alkynes in the presence of B(CF) provides 4,5-diarylphenanthrenes in good yields with excellent regioselectivity. The use of internal alkyne substrates enabled the synthesis of sterically hindered 3,4,5,6-tetrasubstituted phenanthrenes displaying augmented backbone helicity. Furthermore, 1,5-disubstituted, 1,8-disubstituted, 1,2,5,6-tetrasubstituted, and 1,2,7,8-tetrasubstituted phenanthrenes can be obtained through the reaction of alkynes with 1,3-benzenediacetaldehyde or 1,2-benzenediacetaldehyde disilyl acetal.
描述了空间位阻菲的合成——酸催化双环化反应。在B(CF)存在下，用末端芳基炔烃处理1,4 -苯二乙醛，以良好的产率和优异的区域选择性得到4,5 -二芳基菲。使用内炔底物能够合成显示出增强主链螺旋度的空间位阻3,4,5,6 -四取代菲。此外，通过炔烃与1,3 -苯二乙醛或1,2 -苯二乙醛二硅基缩醛的反应，可以得到1,5 -二取代、1,8 -二取代、1,2,5,6 -四取代和1,2,7,8 -四取代菲。
