Metal-Free Synthesis of α-Iodoenones

  • Author: ChemistryViews.org
  • Published: 09 October 2018
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Journal of Organic Chemistry/ACS Publications
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Metal-Free Synthesis of α-Iodoenones

α-Iodoenones (pictured) are useful intermediates in organic synthesis. They can serve as substrates for C–C cross-coupling reactions, leading to α-carbon-substituted enone derivatives. However, most syntheses of α-iodoenones require metal catalysts.


Alfredo Ballesteros and colleagues, University of Oviedo, Spain, have developed a metal-free synthesis of α-iodoenones from propargylic esters. The team used propargylic tosylate or acetate esters as substrates and bis(pyridine) iodonium tetrafluoroborate (Barluenga's reagent) as a iodinating agent that also promotes a rearrangement of the propargylic esters. The reaction proceeds at 0 °C within 0.5 h and the desired α-iodoenones are obtained in high yields.


The proposed reaction mechanism involves the activation of the carbon–carbon triple bond by a iodonium cation, followed by a nucleophilic attack of the ester group's oxygen atom on the alkyne, which initiates the rearrangement. The approach can be used for the synthesis of β-unsubstituted, β-substituted, and β,β-disubstituted α-iodoenones.


 

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