The Palladium-Catalyzed Cross-Coupling Reaction of Enol Acetates of α-Bromo Ketones with 1-Alkenyl-, Aryl-, or Alkylboron Compounds; A Facile Synthesis of Ketones and Their Enol Acetates

Article abstract of DOI:10.1246/bcsj.65.2863

The synthesis of stereodefined enol acetates of ketones is readily accomplished by palladium-catalyzed cross-coupling reaction between alkyl-, aryl-, or 1-alkenylboron reagents with enol acetates of α-bromo ketones.Hydroboration of alkene with 9-BBN, followed by coupling with (Z)-2-ethoxy-1-bromoethene gives the enol ether of aldehyde.These enol acetates and ethers are readily deprotected to give corresponding ketones and aldehydes in high yields.