4.8 Article

Transient Protection of Organic Azides from Click Reactions with Alkynes by Phosphazide Formation

Journal

ORGANIC LETTERS
Volume 20, Issue 13, Pages 4126-4130

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01692

Keywords

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Funding

  1. Japan Agency for Medical Research and Development (AMED) [JP18am0101098, JP18am0301024]
  2. Cooperative Research Project of the Research Center for Biomedical Engineering
  3. Research Program of Five-Star Alliance in NJRC Mater. Dev.
  4. JSPS KAKENHI Grant [15H03118, 18H02104, 16H01133, 18H04386, 17H06414, 26350971, 18J11113]
  5. Naito Foundation

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A method for protecting organic azides from click reactions with alkynes is reported. Treatment of azides with Amphos affords phosphazides, which are stable under click reaction conditions and are easily converted back to azides by treatment with elemental sulfur. Thus, the method allows for facile modification of azide compounds via site-selective click reactions.

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