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Metal-Free Oxidative Decarbonylative [3+2] Annulation of Terminal Alkynes with Tertiary Alkyl Aldehydes toward Cyclopentenes

Hua-Xu Zou, Yang Li*, Xu-Heng Yang, Jiannan Xiang, Jin-Heng Li*

*State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China, Email:,

H.-X. Zou, Y. Li, X.-H. Yang, J. Xiang, J.-H. Li, J. Org. Chem., 2018, 83, 8581-8588.

DOI: 10.1021/acs.joc.8b01130

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A metal-free oxidative decarbonylative [3+2] annulation of terminal alkynes with tertiary γ,δ-unsaturated aldehydes provides cyclopentenes, whereas the reaction of terminal alkynes with 2-methyl-2-arylpropanals provides indenes. The reactions offer broad substrate scope and excellent selectivity.

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Key Words

cyclopentenes, TBHP

ID: J42-Y2018