Catalytic Double [2 + 2] Cycloaddition Relay Enabled C-C Triple Bond Cleavage of Yne-Allenones

Heng Li, Wen Juan Hao, Mian Wang, Xue Qin, Shu Jiang Tu, Peng Zhou, Guigen Li, Jianyi Wang, Bo Jiang

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20 Scopus citations

Abstract

An unusual catalytic double [2 + 2] cycloaddition relay reaction of yne-allenones with unactivated alkenes and alkynes has been achieved, which enabled C-C triple-bond cleavage to access more than 60 examples of functionalized phenanthren-9-ols with generally good yields. This reaction provides a regioselective and practical method for the construction of carbocyclic ring systems with a high degree of functional group compatibility. Aside from surveying the scope of this transformation, mechanistic details of this process are provided by conducting systematic theoretical calculations.

Original languageEnglish
Pages (from-to)4362-4366
Number of pages5
JournalOrganic Letters
Volume20
Issue number14
DOIs
StatePublished - Jul 20 2018

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    Li, H., Hao, W. J., Wang, M., Qin, X., Tu, S. J., Zhou, P., Li, G., Wang, J., & Jiang, B. (2018). Catalytic Double [2 + 2] Cycloaddition Relay Enabled C-C Triple Bond Cleavage of Yne-Allenones. Organic Letters, 20(14), 4362-4366. https://doi.org/10.1021/acs.orglett.8b01841