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J Am Chem Soc. 2013 Oct 9;135(40):14936-9. doi: 10.1021/ja407822b. Epub 2013 Sep 27.

Conversion of azides into diazo compounds in water.

Author information

1
Department of Chemistry and ∥Department of Biochemistry, University of Wisconsin-Madison , Madison, Wisconsin 53706, United States.

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.

PMID:
24053717
PMCID:
PMC3940534
DOI:
10.1021/ja407822b
[Indexed for MEDLINE]
Free PMC Article

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