Electrochemical and Photocatalytic Oxidative Coupling of Ketones via Silyl Bis-enol Ethers

Aidan C. Caravana; Benjamin Nagasing; Sandeep Dhanju; Rebekah G. Reynolds; Emily A. Weiss; Regan J. Thomson

doi:10.1021/acs.joc.1c00384

Electrochemical and Photocatalytic Oxidative Coupling of Ketones via Silyl Bis-enol Ethers

Aidan C. Caravana, Benjamin Nagasing, Sandeep Dhanju, Rebekah G. Reynolds, Emily A. Weiss, Regan J. Thomson^*

^*Corresponding author for this work

Chemistry

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

10 Scopus citations

Abstract

Diastereoselective oxidative coupling of ketones through a silyl bis-enol ether intermediate by anodic and photocatalytic oxidation is reported. These methods provide several 1,4-diketones in good yields without the need for stoichiometric metal oxidants. The strategic use of a silicon tether enables the coupling of both aromatic and aliphatic ketones as well as the synthesis of quaternary centers. Cyclic voltammetry is used to gain insight into the oxidation events of the reaction.

Original language	English (US)
Pages (from-to)	6600-6611
Number of pages	12
Journal	Journal of Organic Chemistry
Volume	86
Issue number	9
DOIs	https://doi.org/10.1021/acs.joc.1c00384
State	Published - May 7 2021

Funding

We gratefully acknowledge support from the National Institutes of Health (NIHGMS 1R01GM124089) and from the Air Force Office of Scientific Research (FA9550-20-1-0364).

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.1c00384

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title = "Electrochemical and Photocatalytic Oxidative Coupling of Ketones via Silyl Bis-enol Ethers",

abstract = "Diastereoselective oxidative coupling of ketones through a silyl bis-enol ether intermediate by anodic and photocatalytic oxidation is reported. These methods provide several 1,4-diketones in good yields without the need for stoichiometric metal oxidants. The strategic use of a silicon tether enables the coupling of both aromatic and aliphatic ketones as well as the synthesis of quaternary centers. Cyclic voltammetry is used to gain insight into the oxidation events of the reaction.",

author = "Caravana, {Aidan C.} and Benjamin Nagasing and Sandeep Dhanju and Reynolds, {Rebekah G.} and Weiss, {Emily A.} and Thomson, {Regan J.}",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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doi = "10.1021/acs.joc.1c00384",

language = "English (US)",

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T1 - Electrochemical and Photocatalytic Oxidative Coupling of Ketones via Silyl Bis-enol Ethers

AU - Caravana, Aidan C.

AU - Nagasing, Benjamin

AU - Dhanju, Sandeep

AU - Reynolds, Rebekah G.

AU - Weiss, Emily A.

AU - Thomson, Regan J.

PY - 2021/5/7

Y1 - 2021/5/7

N2 - Diastereoselective oxidative coupling of ketones through a silyl bis-enol ether intermediate by anodic and photocatalytic oxidation is reported. These methods provide several 1,4-diketones in good yields without the need for stoichiometric metal oxidants. The strategic use of a silicon tether enables the coupling of both aromatic and aliphatic ketones as well as the synthesis of quaternary centers. Cyclic voltammetry is used to gain insight into the oxidation events of the reaction.

AB - Diastereoselective oxidative coupling of ketones through a silyl bis-enol ether intermediate by anodic and photocatalytic oxidation is reported. These methods provide several 1,4-diketones in good yields without the need for stoichiometric metal oxidants. The strategic use of a silicon tether enables the coupling of both aromatic and aliphatic ketones as well as the synthesis of quaternary centers. Cyclic voltammetry is used to gain insight into the oxidation events of the reaction.

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JF - Journal of Organic Chemistry

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ER -

Electrochemical and Photocatalytic Oxidative Coupling of Ketones via Silyl Bis-enol Ethers

Abstract

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CCDC 2060657: Experimental Crystal Structure Determination

CCDC 2060656: Experimental Crystal Structure Determination

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Electrochemical and Photocatalytic Oxidative Coupling of Ketones via Silyl Bis-enol Ethers

Abstract

Funding

ASJC Scopus subject areas

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Other files and links

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Datasets

CCDC 2060657: Experimental Crystal Structure Determination

CCDC 2060656: Experimental Crystal Structure Determination

Cite this