Metal-Free Catalytic Reductive Cleavage of Enol Ethers

Karina Chulsky, Roman Dobrovetsky*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


In contrast to the well-known reductive cleavage of the alkyl-O bond, the cleavage of the alkenyl-O bond is much more challenging especially using metal-free approaches. Unexpectedly, alkenyl-O bonds were reductively cleaved when enol ethers were reacted with Et 3 SiH and a catalytic amount of B(C 6 F 5 ) 3 . Supposedly, this reaction is the result of a B(C 6 F 5 ) 3 -catalyzed tandem hydrosilylation reaction and a silicon-assisted β-elimination. A mechanism for this cleavage reaction is proposed based on experiments and density functional theory (DFT) calculations.

Original languageEnglish
Pages (from-to)6804-6807
Number of pages4
JournalOrganic Letters
Issue number21
StatePublished - 2 Nov 2018


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