Synthesis of Decahydrocyclobuta[cd]indene Skeletons: Rhodium(III)-Catalyzed Hydroarylation and Relay Thiophene-Promoted Intramolecular [2+2] Cycloaddition
Synthesis of Decahydrocyclobuta[cd]indene Skeletons: Rhodium(III)-Catalyzed Hydroarylation and Relay Thiophene-Promoted Intramolecular [2+2] Cycloaddition
复制标题
十氢环丁[cd]茚骨架的合成：铑(III)催化的氢芳基化和中继噻吩促进的分子内[2 2]环加成
DOI：
10.1002/adsc.202000825
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发表时间：
2020
影响因子：
5.4
通讯作者：
Lin Guo-Qiang
中科院分区：
文献类型：
--
作者：
Gao Dingding;Wang Feng;Liu Xing-Yu;Feng Kai-Rui;Zhao Jia-Ying;Wang Yu-Hui;Yang Xiao-Di;Tian Ping;Lin Guo-Qiang
通过铑（III）催化的氢芳基化反应和噻吩介导的分子内[2+2]环加成反应合成了十氢环丁并[cd]茚骨架。该串联反应具有广泛的底物范围（24个实例）和良好的官能团相容性。对照实验揭示了硫（S）杂原子的重要作用，因此提出了噻吩促进的双迈克尔加成的尝试性机制来解释这种形式的[2+2]环加成。此外，所得多环产物对乳腺癌细胞系MDA-MB-468表现出强效的抗癌活性。
The preparation of decahydrocyclobuta[cd]indene skeleton was accomplished through rhodium(III)‐catalyzed hydroarylation and relay thiophene‐promoted intramolecular [2+2] cycloaddition. This tandem reaction exhibited broad substrate scope (24 examples) and good functional group compatibility. Control experiments revealed the important role of sulfur (S) heteroatom, thus a tentative mechanism with thiophene‐promoted double Michael additions was proposed to explain this formal [2+2] cycloaddition. Moreover, the resulting polycyclic products displayed potent anti‐cancer activities against breast cancer cell lines MDA‐MB‐468.