CuI catalyzed formation of 1,2,3-triazoles from azides and terminal alkynes (�click chemistry�) was reported in 2002. In the process of synthesizing the required alkynes, often the alkynes will be derivatized with a silicon protecting group, which would need to be removed before reacting. Such a deprotection would involve an extra reaction step; however, our group has developed �native� CuI catalyzed conditions that allow deprotection and the 1,2,3-triazole formation to take place sequentially in one pot. In initial experiments, a significant excess of 1,8-diazabicycloundec-7-ene (DBU) was being used in this context. By more carefully optimizing this reaction, DBU could be used in a �tuned� amount so as maximize percent yield and control overall reaction environment. Preliminary application of the optimized protocol was used in the synthesis of 4,5'-bis-1,2,3-triazole.

Innovation for Cu-catalyzed azide/alkyne click chemistry: Synthesis of 4,5'-bis-1,2,3-triazoles

243rd National Meeting (2012)

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