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

Amy H. Yap; Steven M. Weinreb

doi:10.1016/j.tetlet.2006.03.020

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

Amy H. Yap, Steven M. Weinreb

Chemistry

Research output: Contribution to journal › Article › peer-review

63 Scopus citations

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 language	English (US)
Pages (from-to)	3035-3038
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2006.03.020
State	Published - May 1 2006

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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

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.",

author = "Yap, {Amy H.} and Weinreb, {Steven M.}",

note = "Funding Information: We are grateful to the National Institutes of Health (CA-034303) for financial support of this research. We also thank Dr. G. Jia for providing details on the preparation of the ruthenium catalyst. ",

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T1 - β-Tosylethylazide

T2 - a useful synthon for preparation of N-protected 1,2,3-triazoles via click chemistry

AU - Yap, Amy H.

AU - Weinreb, Steven M.

N1 - Funding Information: We are grateful to the National Institutes of Health (CA-034303) for financial support of this research. We also thank Dr. G. Jia for providing details on the preparation of the ruthenium catalyst.

PY - 2006/5/1

Y1 - 2006/5/1

N2 - 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.

AB - 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.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

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

Abstract

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