The DOI matches its Crossref record; 2 of the 2 references it cites were found in a registry or an index.
Click Chemistry beyond Metal‐Catalyzed Cycloaddition
Abstract
No copper needed: In recent years, a large number of metal‐free click reactions have been reported based on thiol‐ene radical additions, Diels–Alder reactions, and Michael additions. In this Minireview, special attention is given to the advantages and limitations of the different methods to evaluate whether they have the potential to surpass the overwhelming success of the copper(I)‐catalyzed azide‐alkyne cycloaddition.magnified image The overwhelming success of click chemistry encouraged researchers to develop alternative “spring‐loaded” chemical reactions for use in different fields of chemistry. Initially, the copper(I)‐catalyzed azide‐alkyne cycloaddition was the only click reaction. In recent years, metal‐free [3+2] cycloaddition reactions, Diels–Alder reactions, and thiol‐alkene radical addition reactions have come to the fore as click reactions because of their simple synthetic procedures and high yields. Furthermore, these metal‐free reactions have wide applicability and are physiologically compatible. These and other alternative click reactions expand the opportunities for synthesizing small organic compounds as well as tailor‐made macromolecules and bioconjugates. This Minireview discusses the success and applicability of new, in particular metal‐free, click reactions.
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Citations
Cites
CuI‐Catalyzed Alkyne–Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective
Bock, V. D., Hiemstra, H., & van Maarseveen, J. H. (2006) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200500483 · Cited by 1,452
The convergence of synthetic organic and polymer chemistries
Hawker, C. J., & Wooley, K. L. (2005) · Science · doi:10.1126/science.1109778 · Cited by 1,298
Cited by
Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis
Hoyle, C. E., Lowe, A. B., & Bowman, C. N. (2010) · Chemical Society Reviews · doi:10.1039/b901979k · Cited by 1,639
Thiol-ene “click” reactions and recent applications in polymer and materials synthesis
Lowe, A. B. (2010) · Polym. Chem. · doi:10.1039/b9py00216b · Cited by 1,563
Hydrogels in a historical perspective: From simple networks to smart materials
Buwalda, S. J., Boere, K. W. M., Dijkstra, P. J., Feijen, J., Vermonden, T., & Hennink, W. E. (2014) · Journal of Controlled Release · doi:10.1016/j.jconrel.2014.03.052 · Cited by 994
Marrying click chemistry with polymerization: expanding the scope of polymeric materials
Golas, P. L., & Matyjaszewski, K. (2010) · Chem. Soc. Rev. · doi:10.1039/b901978m · Cited by 863
Designing degradable hydrogels for orthogonal control of cell microenvironments
Kharkar, P. M., Kiick, K. L., & Kloxin, A. M. (2013) · Chem. Soc. Rev. · doi:10.1039/c3cs60040h · Cited by 717
Metadata
- Authors
- Becer, C. R., Hoogenboom, R., & Schubert, U. S.
- Venue
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Published
- 2009-06-17
- Volume
- 48
- Issue
- 27
- Pages
- 4900-4908
- ISSN
- 1433-7851 (ISSN-L)
- 1521-3773
- OpenAlex
- W2113007722
- Cited by
- 866
- References
- 2
- FWCI
- 47.89
- Type
- journal article
- Language
- en
- Open access
- closed
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- Becer, C. R., Hoogenboom, R., & Schubert, U. S. (2009). Click Chemistry beyond Metal‐Catalyzed Cycloaddition. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.200900755
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