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Copper-Catalyzed Oxidative Cyclization of 1,5-Enynes with Concomitant C–C Bond Cleavage: An Unexpected Access to 3‑Formyl-1-indenone Derivatives

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journal contribution
posted on 06.06.2014, 00:00 by Jian Zhang, Degui Wu, Xiaoling Chen, Yunkui Liu, Zhenyuan Xu
A Cu(0)/Selectfluor system-mediated oxidative cyclization of 1,5-enynes with concomitant C–C bond cleavage to access 3-formyl-1-indenone derivatives is described. Preliminary mechanistic investigations disclosed that the C–C bond cleavage involved a novel water-participated oxygen-insertion β-carbon elimination through double oxycuprations.