Microwave-assisted click chemistry

CHED 354

Tyler J. Auvil, auvil.2@wright.edu, Benjamin K Southerland, Southerland.2@wright.edu, and Daniel M. Ketcha, daniel.ketcha@wright.edu. Department of Chemistry, Wright State University, 3640 Colonel Glenn Highway, Dayton, OH 45435
The formation of [1,2,3]-triazoles by the regiospecific Cu(I)-catalyzed ligation of organic azides and terminal alkynes represents an increasingly important reaction process in organic chemistry. The reported one-pot synthesis of 1,2,3-triazoles by the 1,3-dipolar cycloaddition of in situ generated azides and alkynes using CuSO4 and sodium ascorbate or Cu(II)/copper wire appears ideally suited for the undergraduate laboratory since the pure product can be isolated in high yields by simple precipitation and subsequent filtration. Whereas the typical thermal parameters of the reaction require two successive overnight heating periods, the use of the microwave enables students to run a reaction, do the work-up, and characterize the product, all in one laboratory period. Examples of this process under microwave conditions in a variety of solvents and also using copper acetate as sole catalyst will be delineated.