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In the Laboratory
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Just Click It: Undergraduate Procedures for the Copper(I)-Catalyzed Formation of 1,2,3-Triazoles from Azides and Terminal Acetylenes
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William D. Sharpless
Department of Chemistry, Grinnell College, Grinnell, IA 50112; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037
Peng Wu and Trond Vidar Hansen
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037
James G. Lindberg
Department of Chemistry, Grinnell College, Grinnell, IA 50112
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December 2005
Vol. 82 No. 12
p. 1833
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| Abstract |
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A procedure for copper(I)-catalyzed triazole synthesis using azides and terminal acetylenes introduces undergraduate organic students to the growing world of click chemistry. The reaction is ideal for the undergraduate laboratory as, in keeping with the defining aspects of click chemistry, it is high-yielding, requires no chromatography, is easily monitored by TLC, and displays distinct peaks in both IR and 1H-NMR. Virtually all products precipitate, and with just a few different starting blocks every student, or pair of lab partners, can produce a unique "clicked" compound. Additionally, general procedures for in situ azide synthesis and phenol propargylation provide a vehicle for chemical discovery and creativity well beyond the mini-libraries presented.
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| Supplement |
Experimental details for procedures A, B, and C; notes for the instructor; and 1H-NMR spectra for all isolated compounds are available.
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| More Information |
Citation |
Sharpless, William D.; Wu, Peng; Hansen, Trond Vidar; Lindberg, James G. J. Chem. Educ. 2005 82 1833.
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Keywords |
Alkynes; Catalysis; Hands-On Learning / Manipulatives; Heterocycles; IR Spectroscopy; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Reactions; Second-Year Undergraduate; Synthesis; Thin Layer Chromatography; Upper-Division Undergraduate
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History |
Created:
Last Updated: |
October 25, 2005
November 4, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
2005
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December
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1833
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