在银/钴接力催化下，通过双炔丙基膦酸酯的串联[3,3] - 西格玛重排/[2 + 2]环加成反应制备取代环丁烯。
Access to substituted cyclobutenes by tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition of dipropargylphosphonates under Ag/Co relay catalysis.
作者信息
Ni Qijian, Song Xiaoxiao, Png Chin Wen, Zhang Yongliang, Zhao Yu
机构信息
Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science, Anhui Normal University Wuhu 241002 Anhui China.
Department of Chemistry, National University of Singapore 3 Science Drive 3 Singapore 117543 Singapore
出版信息
Chem Sci. 2020 Oct 16;11(45):12329-12335. doi: 10.1039/d0sc02972f.
We present herein an unconventional tandem [3,3]-sigmatropic rearrangement/[2 + 2] cycloaddition of simple dipropargylphosphonates to deliver a range of bicyclic polysubstituted cyclobutenes and cyclobutanes under Ag/Co relay catalysis. An interesting switch from allene-allene to allene-alkyne cycloaddition was observed based on the substitution of the substrates, which further diversified the range of compounds accessible from this practical method. Significantly, preliminary biological screening of these new compounds identified promising candidates as suppressors of cellular proliferation.
我们在此展示了一种非传统的串联[3,3]-σ迁移重排/[2 + 2]环加成反应，即简单的二炔丙基膦酸酯在银/钴接力催化下反应，生成一系列双环多取代环丁烯和环丁烷。基于底物的取代情况，观察到了从丙二烯-丙二烯环加成到丙二烯-炔烃环加成的有趣转变，这进一步拓展了通过这种实用方法可获得的化合物范围。值得注意的是，对这些新化合物的初步生物学筛选确定了有前景的候选物作为细胞增殖抑制剂。
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