Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes

Org Lett. 2020 Nov 6;22(21):8365-8369. doi: 10.1021/acs.orglett.0c02988. Epub 2020 Oct 19.


A direct assembly of secondary benzylureas and related amine derivatives via copper-catalyzed carboamination of styrenes with potassium alkyltrifluoroborates and ureas, anilines, or an amide is reported. Terminal and 1,2-disubstituted alkenes, as well as dienes, participate in this three-component coupling reaction. The reaction mechanism likely involves the addition of an alkyl radical to the styrene, followed by metal-mediated oxidative coupling of the resulting benzylic radical with the amine derivative. Factors that impact substrate reactivity and regioselectivity are discussed.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkenes / chemistry
  • Amines / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Copper / chemistry*
  • Styrene / chemistry*
  • Urease / chemical synthesis*
  • Urease / chemistry*


  • Alkenes
  • Amines
  • Styrene
  • Copper
  • Urease