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Updated: Feb 3, 2026

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Published on: April 10, 2018
Metal-Free Catalytic Reductive Cleavage of Enol Ethers
Karina Chulsky1, Roman Dobrovetsky1
1School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences , Tel Aviv University , Tel Aviv 69978 , Israel.
Abstract:
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 Et3SiH and a catalytic amount of B(C6F5)3. Supposedly, this reaction is the result of a B(C6F5)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.
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