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

Research output: Contribution to journalArticlepeer-review

5 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 languageEnglish (US)
Pages (from-to)6600-6611
Number of pages12
JournalJournal of Organic Chemistry
Volume86
Issue number9
DOIs
StatePublished - May 7 2021

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Electrochemical and Photocatalytic Oxidative Coupling of Ketones via Silyl Bis-enol Ethers'. Together they form a unique fingerprint.

Cite this