Copper(I)-Catalyzed Cycloaddition of Organic Azides and 1-Iodoalkynes

Authors


  • We gratefully acknowledge financial support from the National Institutes of Health, National Institutes of General Medical Sciences (GM28384 to K.B.S., GM087620 and GM083658 to V.V.F.) and the Skaggs Institute for Chemical Biology. Postdoctoral fellowships were provided by the NIH (J.C.T) and NSERC (J.E.H).

Abstract

original image

High fidelity: 1-Iodoalkynes react rapidly and selectively with organic azides in the presence of copper(I) catalysts (see scheme; TTTA=tris((1-tert-butyl-1H-1,2,3-triazolyl)methyl)amine). The reaction is compatible with many functional groups and solvents, and 5-iodotriazole products were usually obtained in excellent yield. These products can be further functionalized to give fully substituted 1,2,3-triazoles.

Ancillary