Metal-Free Catalytic Reductive Cleavage of Enol Ethers

Karina Chulsky; Roman Dobrovetsky

doi:10.1021/acs.orglett.8b02932

Metal-Free Catalytic Reductive Cleavage of Enol Ethers

Karina Chulsky, Roman Dobrovetsky^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

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 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 language	English
Pages (from-to)	6804-6807
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	21
DOIs	https://doi.org/10.1021/acs.orglett.8b02932
State	Published - 2 Nov 2018

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Tel Aviv University

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10.1021/acs.orglett.8b02932

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title = "Metal-Free Catalytic Reductive Cleavage of Enol Ethers",

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 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.",

author = "Karina Chulsky and Roman Dobrovetsky",

note = "Publisher Copyright: Copyright {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acs.orglett.8b02932",

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AU - Chulsky, Karina

AU - Dobrovetsky, Roman

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N2 - 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.

AB - 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.

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JO - Organic Letters

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Metal-Free Catalytic Reductive Cleavage of Enol Ethers

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