Cu2O nanoparticle-catalyzed synthesis of diaryl tetrazolones and investigation of their solid-state properties

Thomas E. Reason, Benjamin Goka, Jeanette A. Krause, Abelline K. Fionah, Elsayed M. Zahran, Sundeep Rayat

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient and versatile method for the synthesis of 1,4-diaryl tetrazolones1is reported which involves C-N coupling of aryl tetrazolones2with aryl boronic acids3in the presence of Cu2O nanoparticles under an oxygen atmosphere and DMSO as solvent. The reaction tolerates a variety of electron donating and electron withdrawing substituents on both substrates and produces the desired 1,4-diaryl tetrazolones1in moderate to good yields. In the crystal lattice, the molecules exhibit π⋯π stacking interactions between the adjacent layers as well as weak through-space electrostatic C-H⋯O interactions involving the pendant rings and tetrazolone carbonyl. 1-(4-Methoxyphenyl)-4-(3-tolyl)-1,4-dihydro-5H-tetrazol-5-one1bkand 1-(3-fluorophenyl)-4-(4-methoxyphenyl)-1,4-dihydro-5H-tetrazol-5-one1be, differing only in the presence of one group (methyl or fluoro), exhibited an identical pattern of noncovalent interactions in the solid-state. Hirshfeld surface analyses have also been performed to visualize intermolecular interactions.

Original languageEnglish (US)
Pages (from-to)3220-3229
Number of pages10
JournalCrystEngComm
Volume23
Issue number17
DOIs
StatePublished - May 7 2021
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

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