β-Tosylethylazide: a useful synthon for preparation of N-protected 1,2,3-triazoles via click chemistry

Amy H. Yap, Steven M. Weinreb

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

β-Tosylethylazide (TSE-N3), which can be prepared in one step from p-tolyl vinyl sulfone and sodium azide/H2SO4, undergoes metal-catalyzed 1,3-dipolar cycloadditions with alkynes to produce TSE-protected 1,2,3-triazoles. The protecting group can be removed using potassium tert-butoxide in THF at -78 to 0 °C.

Original languageEnglish (US)
Pages (from-to)3035-3038
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number18
DOIs
StatePublished - May 1 2006

Fingerprint

Click Chemistry
Sodium Azide
Triazoles
Alkynes
Cycloaddition
Cycloaddition Reaction
Metals
potassium tert-butoxide
divinyl sulfone

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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β-Tosylethylazide : a useful synthon for preparation of N-protected 1,2,3-triazoles via click chemistry. / Yap, Amy H.; Weinreb, Steven M.

In: Tetrahedron Letters, Vol. 47, No. 18, 01.05.2006, p. 3035-3038.

Research output: Contribution to journalArticle

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