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.

JOURNAL:
Organic Letters

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

DOI:
https://doi.org/10.1021/acs.orglett.8b01692

Takamitsu HOSOYA, Ph.D.,Professor
Suguru YOSHIDA, Ph.D., Associate Professor
Department of Chemical Bioscience,
Institute of Biomaterials and Bioengineering,
Tokyo Medical and Dental University(TMDU)
E-mail:thosoya.cb(at)tmd.ac.jp （HOSOYA）
　　　s-yoshida.cb(at)tmd.ac.jp （YOSHIDA）