Catalytic copper-mediated ring opening and functionalization of benzoxazoles

MacArena Corro, Maria Besora, Celia Maya, Eleuterio Álvarez, Juan Urbano, Manuel R. Fructos, Feliu Maseras, Pedro J. Pérez

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9 Citations (Scopus)

Abstract

© 2014 American Chemical Society. A novel reaction involving benzoxazole, ethyl diazoacetate, and water has been discovered, with TpBr3Cu(NCMe) (TpBr3 = hydrotris(3,4,5-tribromopyrazolyl)borate) as the catalyst. The fused azoles are converted into highly functionalized substituted benzenes bearing aldehyde, amine carboxylate and hydroxyl groups. The protocol has been applied for a series of benzoxazoles with several diazo compounds. Experimental data and theoretical calculations have led to a mechanistic proposal that includes carbene addition, ylide formation, and water addition to the latter, all those steps being catalyzed by the copper center.
Original languageEnglish
Pages (from-to)4215-4222
JournalACS Catalysis
Volume4
Issue number11
DOIs
Publication statusPublished - 13 Oct 2014

Keywords

  • benzoxazole functionalization
  • benzoxazole ring opening
  • carbene transfer
  • copper catalysis
  • ethyl diazoacetate

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