2010 Summer NC State Undergraduate Research Symposium

Session Time : 8/5/10 1:00 PM - 8/5/10 4:00 PM

Content Area : NSF Chemistry REU

Student Presenters :
Joshua Brett Hill Chemistry

Mentors and/or Co-Authors :
Ana Ison Chemistry

Abstract Title : Synthesis of a Copper(I) Carbene for Catalysis of Azide-Terminal Alkyne Click Chemistry

Abstract :
The importance of catalysis in organic synthesis is largely unexplored in the undergraduate laboratory. The set of experiments described here will introduce students to the click-synthesis of 1,2,3 triazoles catalyzed by Cu(I) carbene complexes. Click chemistry is an example of modern organic synthetic chemistry marked by the use of readily available substrates, benign solvents, and high yields. In this multi-step experiment we synthesized glyoxal-bis (2,4,6-trimethylphenyl)imine (1) followed by reduction with NaBH4 to form N,N’ (2,4,6-trimethylphenyl)amine dihydrochloride (2). Compound 2 was further reacted with triethyl orthoformate by microwave assisted synthesis to form the carbene precursor, N,N’-bis(2,4,6-trimethylphenyl) imidazolinium chloride (SIMes HCl). The carbene precursor (SIMes HCl) was finally coordinated to Cu(I) to form the catalyst [(SIMes)CuCl]. The catalyst can then be used in the [3+2] cycloaddition of azides and terminal acetylenes to obtain 1,2,3 triazoles. All compounds were fully characterized by 1H-NMR and FTIR spectroscopy and were found to be of high purity.