Electrochemical Dearomatizing Spirocyclization of Alkynes with Dimethyl 2-Benzylmalonates to Spiro[4.5]deca-trienones.

An electrochemical dearomatizing spirocyclization of alkynes with dimethyl 2-benzylmalonates for the preparation of spiro[4.5]deca-trienones has been developed. This approach adopts ferrocene (Cp2Fe) as an electrocatalyst to produce carbon-centered radical intermediates from C-H-based malonates, which obviates the forthputting of noble-metal reagents, sacrificial chemical oxidants and 2-bromomalonates. A wide variety of spiro compounds are efficiently prepared with satisfactory results under mild conditions.

Citation

Laiqiang Li, Zhong-Wei Hou, Pinhua Li, Lei Wang. Electrochemical Dearomatizing Spirocyclization of Alkynes with Dimethyl 2-Benzylmalonates to Spiro[4.5]deca-trienones. The Journal of organic chemistry. 2022 Jul 01;87(13):8697-8708

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PMID: 35679486

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