Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations

Riley L. Svec, Paul J. Hergenrother

Research output: Contribution to journalArticle

Abstract

Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chemistry of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Herein, we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazonium reagents. TMZ was employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that methyl ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a commercially available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.

Original languageEnglish (US)
Pages (from-to)1857-1862
Number of pages6
JournalAngewandte Chemie - International Edition
Volume59
Issue number5
DOIs
StatePublished - Jan 27 2020

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Keywords

  • alkylation
  • cyclopropanation
  • diazo compounds
  • diazomethane
  • imidazotetrazines

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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