Just Click It: Undergraduate Procedures for the Copper(I)-Catalyzed Formation of 1,2,3-Triazoles from Azides and Terminal Acetylenes

Trond Vidar Hansen and Peng Wu
Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037
William D. Sharpless
Department of Chemistry, Grinnell College, Grinnell, IA 50112; Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037
James G. Lindberg
Department of Chemistry, Grinnell College, Grinnell, IA 50112
J. Chem. Educ., 2005, 82 (12), p 1833
DOI: 10.1021/ed082p1833
Publication Date (Web): December 1, 2005

Abstract

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Catalysis
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  • Received: August 03, 2009

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