Suzuki Coupling of Protected Aryl Diazonium Ions: Expanding the Knowledge of Triazabutadiene Compatible Reactions

Abigail J. Shepard, Julia A. Townsend, Christopher Foley, Christopher Hulme, Michael T. Marty, John C. Jewett

Research output: Contribution to journalArticlepeer-review

Abstract

Aryl diazonium ions are important in synthesis and chemical biology, and the acid-labile triazabutadiene can protect this handle for future use. We report a Suzuki coupling strategy that is compatible with the triazabutadiene scaffold, expanding the scope of synthetically available triazabutadienes. Shown herein, the triazabutadiene scaffold remains intact and reactive after coupling, as demonstrated by releasing the aryl diazonium ion to label a tyrosine-rich model protein.

Original languageEnglish (US)
Pages (from-to)1851-1855
Number of pages5
JournalOrganic Letters
Volume23
Issue number5
DOIs
StatePublished - Mar 5 2021

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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