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Heterogeneous Copper Catalyst for the Cycloaddition of Azides and Alkynes without Additives under Ambient Conditions

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In Soo Park,^† Min Serk Kwon,^† Youngkwon Kim,^‡ Jae Sung Lee,^‡ and Jaiwook Park*^†

Department of Chemistry and Department of Chemical Engineering, Pohang University of Science and Technology (POSTECH), San 31 Hyojadong, Pohang, Kyeongbuk 790-784, Republic of Korea

Org. Lett., 2008, 10 (3), pp 497–500

DOI: 10.1021/ol702790w

Publication Date (Web): January 9, 2008

Section:

Heterocyclic Compounds (More than One Hetero Atom)

Abstract

A new copper catalyst was developed by immobilizing copper nanoparticles in aluminum oxyhydoxide fiber. The catalyst showed high catalytic activity for the (3 + 2) Huisgen cycloaddition of nonactivated alkynes as well as activated ones with various azides at room temperature. The catalyst was recycled five times without significant loss of activity.

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Citing Articles

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This article has been cited by 5 ACS Journal articles (5 most recent appear below).

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- Cu-Based Nanoalloys in the Base-Free Ullmann Heterocyle-Aryl Ether Synthesis
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  Organic Process Research & Development2010 14 (3), 644-649
  We report the first liquid−liquid Ullmann etherification process mediated not only by oxidatively stable Cu but also by CuZn and CuSn nanoparticle catalysts in conjunction with microwave heating that also avoids the use of solid and expensive bases. ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Ultrasound-Promoted Copper-Catalyzed Azide−Alkyne Cycloaddition
Giancarlo Cravotto, Valery V. Fokin, Davide Garella, Arianna Binello, Luisa Boffa and Alessandro Barge
Journal of Combinatorial Chemistry2010 12 (1), 13-15
- Ultrasound-Promoted Copper-Catalyzed Azide−Alkyne Cycloaddition
  Giancarlo Cravotto, Valery V. Fokin, Davide Garella, Arianna Binello, Luisa Boffa and Alessandro Barge
  Journal of Combinatorial Chemistry2010 12 (1), 13-15
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Apparent Copper(II)-Accelerated Azide−Alkyne Cycloaddition
Wendy S. Brotherton, Heather A. Michaels, J. Tyler Simmons, Ronald J. Clark, Naresh S. Dalal and Lei Zhu
Organic Letters2009 11 (21), 4954-4957
- Apparent Copper(II)-Accelerated Azide−Alkyne Cycloaddition
  Wendy S. Brotherton, Heather A. Michaels, J. Tyler Simmons, Ronald J. Clark, Naresh S. Dalal and Lei Zhu
  Organic Letters2009 11 (21), 4954-4957
  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 ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Heterogeneous Catalysis of a Copper-Coated Atomic Force Microscopy Tip for Direct-Write Click Chemistry
Walter F. Paxton, Jason M. Spruell and J. Fraser Stoddart
Journal of the American Chemical Society2009 131 (19), 6692-6694
- Heterogeneous Catalysis of a Copper-Coated Atomic Force Microscopy Tip for Direct-Write Click Chemistry
  Walter F. Paxton, Jason M. Spruell and J. Fraser Stoddart
  Journal of the American Chemical Society2009 131 (19), 6692-6694
  We report a constructive scanning probe lithography method that uses heterogeneous copper-coated atomic force microscopy tips to catalyze azide−alkyne cycloadditions (CuAAC) between solvated terminal alkyne molecules and azide-terminated self-assembled ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Concise and Diversity-Oriented Synthesis of Ligand Arm-Functionalized Azoamides
Damijana Urankar and Janez Košmrlj
Journal of Combinatorial Chemistry2008 10 (6), 981-985
- Concise and Diversity-Oriented Synthesis of Ligand Arm-Functionalized Azoamides
  Damijana Urankar and Janez Košmrlj
  Journal of Combinatorial Chemistry2008 10 (6), 981-985
  Azoamides, previously established as bioactive intracellular GSH-depleting agents, were decorated with a terminal alkyne moiety to 4 and then were transformed, by copper(I)-catalyzed azide−alkyne cycloaddition (CuAAC), into different ligand-arm ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links