Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes

Jason E. Hein, Jonathan C. Tripp, Larissa B. Krasnova, K. Barry Sharpless, Valery V. Fokin

Research output: Contribution to journalArticle

310 Citations (Scopus)

Abstract

High fidelity: 1-Iodoalkynes react rapidly and selectively with organic azides in the presence of copper(I) catalysts (see scheme; TTTA=tris((1-tert- butyl-1H-1,2,3-triazolyl)methyl)amine). The reaction is compatible with many functional groups and solvents, and 5-iodotriazole products were usually obtained in excellent yield. These products can be further functionalized to give fully substituted 1,2,3-triazoles.

Original languageEnglish
Pages (from-to)8018-8021
Number of pages4
JournalAngewandte Chemie - International Edition
Volume48
Issue number43
DOIs
Publication statusPublished - 12 Oct 2009
Externally publishedYes

Fingerprint

Triazoles
Azides
Cycloaddition
Functional groups
Amines
Copper
Catalysts

Keywords

  • Azides
  • Click chemistry
  • Copper
  • Cycloaddition
  • Iodoalkynes
  • Iodotriazoles

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Hein, J. E., Tripp, J. C., Krasnova, L. B., Sharpless, K. B., & Fokin, V. V. (2009). Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes. Angewandte Chemie - International Edition, 48(43), 8018-8021. https://doi.org/10.1002/anie.200903558

Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes. / Hein, Jason E.; Tripp, Jonathan C.; Krasnova, Larissa B.; Sharpless, K. Barry; Fokin, Valery V.

In: Angewandte Chemie - International Edition, Vol. 48, No. 43, 12.10.2009, p. 8018-8021.

Research output: Contribution to journalArticle

Hein, JE, Tripp, JC, Krasnova, LB, Sharpless, KB & Fokin, VV 2009, 'Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes', Angewandte Chemie - International Edition, vol. 48, no. 43, pp. 8018-8021. https://doi.org/10.1002/anie.200903558
Hein, Jason E. ; Tripp, Jonathan C. ; Krasnova, Larissa B. ; Sharpless, K. Barry ; Fokin, Valery V. / Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes. In: Angewandte Chemie - International Edition. 2009 ; Vol. 48, No. 43. pp. 8018-8021.
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