Apparent Copper(II)-Accelerated Azide−Alkyne Cycloaddition

Cu(II) salts accelerate azide−alkyne cycloaddition reactions in alcoholic solvents without reductants such as sodium ascorbate. Spectroscopic observations suggest that Cu(II) undergoes reduction to catalytic Cu(I) species via either alcohol oxidation or alkyne homocoupling, or both, during an induct...

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Bibliographic Details
Published in:Organic letters 2009-11, Vol.11 (21), p.4954-4957
Main Authors: Brotherton, Wendy S, Michaels, Heather A, Simmons, J. Tyler, Clark, Ronald J, Dalal, Naresh S, Zhu, Lei
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Azides - chemistry
Catalysis
Combinatorial Chemistry Techniques
Copper - chemistry
Cyclization
Molecular Structure
Oxidation-Reduction
Propanols - chemistry
Triazoles - chemical synthesis
Triazoles - chemistry
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Summary:Cu(II) salts accelerate azide−alkyne cycloaddition reactions in alcoholic solvents without reductants such as sodium ascorbate. Spectroscopic observations suggest that Cu(II) undergoes reduction to catalytic Cu(I) species via either alcohol oxidation or alkyne homocoupling, or both, during an induction period. The reactions involving 2-picolylazide are likely facilitated by its chelation to Cu(II). The highly exothermic reaction between 2-picolylazide and propargyl alcohol completes within 1−2 min in the presence of as low as 1 mol % Cu(OAc)2.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9021113