Radical condensation between benzylic alcohols and acetamides to form 3-arylpropanamides. Issue 30 (15th July 2020)

• Record Type: Journal Article
• Authors: Azizi, Kobra; Madsen, Robert
• Is Part Of: Chemical science. Volume 11:Issue 30(2020)
• Page Start: 7800
• Page End: 7806
• Publication Date: 2020-07-15
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc02948c
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Benzylic alcohols and acetamides are coupled into 3-arylpropanamides by a new radical condensation through the radical anion of the alcohol. Abstract : A new radical condensation reaction is developed where benzylic alcohols and acetamides are coupled to generate 3-arylpropanamides with water as the only byproduct. The transformation is performed with potassium tert -butoxide as the only additive and gives rise to a variety of 3-arylpropanamides in good yields. The mechanism has been investigated experimentally with labelled substrates, trapping experiments and spectroscopic measurements. The findings indicate a radical pathway where potassium tert -butoxide is believed to serve a dual role as both base and radical initiator. The radical anion of the benzylic alcohol is proposed as the key intermediate, which undergoes coupling with the enolate of the amide to form the new C–C bond. Subsequent elimination to the corresponding cinnamamide and olefin reduction then affords the 3-arylpropanamides.