Copper(I)‐Catalyzed Cycloaddition of Organic Azides and 1‐Iodoalkynes

Copper(I)‐Catalyzed Cycloaddition of Organic Azides and 1‐Iodoalkynes

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 o...

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Veröffentlicht in:Angewandte Chemie International Edition 2009-01, Vol.48 (43), p.8018-8021
Hauptverfasser: Hein, Jason E., Tripp, Jonathan C., Krasnova, Larissa B., Sharpless, K. Barry, Fokin, Valery V.
Format: Artikel
Sprache:eng
Schlagworte:
azides
Azides - chemistry
Catalysis
click chemistry
copper
Copper - chemistry
cycloaddition
Iodine - chemistry
iodoalkynes
iodotriazoles
Triazoles - chemistry
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200903558