Conversion of azides into diazo compounds in water

Ho-Hsuan Chou, Ronald T. Raines

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Diazo compounds are in widespread use in synthetic organic chemistry but have untapped potential in chemical biology. We report on the design and optimization of a phosphinoester that mediates the efficient conversion of azides into diazo compounds in phosphate buffer at neutral pH and room temperature. High yields are maintained in the presence of common nucleophilic or electrophilic functional groups, and reaction progress can be monitored by colorimetry. As azido groups are easy to install and maintain in biopolymers or their ligands, this new mode of azide reactivity could have substantial utility in chemical biology.

Original languageEnglish
Pages (from-to)14936-14939
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number40
DOIs
Publication statusPublished - 2013 Oct 21

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Azides
Organic Chemistry
Colorimetry
Biopolymers
Water
Functional groups
Buffers
Phosphates
Ligands
Temperature

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Chou, Ho-Hsuan ; Raines, Ronald T. / Conversion of azides into diazo compounds in water. In: Journal of the American Chemical Society. 2013 ; Vol. 135, No. 40. pp. 14936-14939.
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Conversion of azides into diazo compounds in water. / Chou, Ho-Hsuan; Raines, Ronald T.

In: Journal of the American Chemical Society, Vol. 135, No. 40, 21.10.2013, p. 14936-14939.

Research output: Contribution to journalArticle

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