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

Tomohiro Meguro, Suguru Yoshida, Kazunobu Igawa, Katsuhiko Tomooka, Takamitsu Hosoya

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4126-4130
Number of pages5
JournalOrganic Letters
Volume20
Issue number13
DOIs
Publication statusPublished - Jul 6 2018

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azides (organic)
Alkynes
Azides
alkynes
sulfur
Sulfur
3'-azido-2',3'-dideoxythymidine 5'-H-phoshonate

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Transient Protection of Organic Azides from Click Reactions with Alkynes by Phosphazide Formation. / Meguro, Tomohiro; Yoshida, Suguru; Igawa, Kazunobu; Tomooka, Katsuhiko; Hosoya, Takamitsu.

In: Organic Letters, Vol. 20, No. 13, 06.07.2018, p. 4126-4130.

Research output: Contribution to journalArticle

Meguro, Tomohiro ; Yoshida, Suguru ; Igawa, Kazunobu ; Tomooka, Katsuhiko ; Hosoya, Takamitsu. / Transient Protection of Organic Azides from Click Reactions with Alkynes by Phosphazide Formation. In: Organic Letters. 2018 ; Vol. 20, No. 13. pp. 4126-4130.
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