Synthesis of Sterically Hindered 4,5-Diarylphenanthrenes via Acid-catalyzed Bisannulation of Benzenediacetaldehydes with Alkynes
Synthesis of Sterically Hindered 4,5-Diarylphenanthrenes via Acid-catalyzed Bisannulation of Benzenediacetaldehydes with Alkynes
复制标题
通过酸催化苯二乙醛与炔烃双环化合成空间位阻 4,5-二芳基菲
DOI：
10.1039/c9sc00334g
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发表时间：
2019
期刊：
影响因子：
8.4
通讯作者：
Kenichiro Itami
中科院分区：
文献类型：
--
作者：
Yuanming Li;Akiko Yagi;Kenichiro Itami
介绍了酸催化双环化反应合成位阻菲的方法。在B(C6F5)3存在的情况下，用末端芳基炔处理1,4-苯二乙醛，得到产率高且具有优异区域选择性的4,5-二苯基菲。使用内炔底物可以合成具有增强主螺旋结构的3,4,5,6-四取代菲。此外，1,5-二取代、1,8-二取代、1,2,5,6-四取代和1,2,7,8-四取代的菲可以通过炔与1,3-苯二乙醛或1,2-苯二乙醛二烷基缩醛反应得到。
The synthesis of sterically hindered phenanthrenes via acid-catalyzed bisannulation reaction is described. Treatment of 1,4-benzenediacetaldehyde with terminal aryl alkynes in the presence of B(C6F5)3 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.