The DOI matches its Crossref record; 30 of the 30 references it cites were found in a registry or an index.
Nucleophile-Initiated Thiol-Michael Reactions: Effect of Organocatalyst, Thiol, and Ene
Abstract
A detailed evaluation of the kinetics of the thiol-Michael reaction between hexanethiol and hexyl acrylate is described. It is shown that primary amines are more effective catalysts than either secondary or tertiary amines with, for example, quantitative conversion being achieved within 500 s in the case of hexylamine with an apparent rate constant of 53.4 mol L −1 s −1 at a catalyst loading of 0.057 mol %. Certain tertiary phosphines, and especially tri- n -propylphosphine and dimethylphenylphosphine, are shown to be even more effective species even at concentrations 2 orders of magnitude lower than employed for hexylamine and performed in solution with quantitative conversions reached within ca. 100 s for both species and apparent rate constants of 1810 and 431 mol L −1 s −1, respectively. The nature of the thiol is also demonstrated to be an important consideration with mercaptoglycolate and mercaptopropionate esters being significantly more reactive than hexanethiol with reactivity mirroring the p K a of the thiols. Likewise, it is shown that the structure of the activated ene is also crucial with the degree of activation and ene-substitution pattern being important features in determining reactivity. In terms of reaction with hexanethiol in the presence of hexylamine as catalyst, it is shown that propylmaleimide > diethyl fumarate > diethyl maleate > dimethylacrylamide > acrylonitrile > ethyl crotonate > ethyl cinnamate > ethyl methacrylate.
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Cites
Hoyle, C. E., & Bowman, C. N. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200903924 · Cited by 4,182
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Tibbitt, M. W., & Anseth, K. S. (2009) · Biotechnology and Bioengineering · doi:10.1002/bit.22361 · Cited by 2,727
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Hoyle, C. E., Lowe, A. B., & Bowman, C. N. (2010) · Chemical Society Reviews · doi:10.1039/b901979k · Cited by 1,639
Self-citationThiol-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
Self-citationMichael addition reactions in macromolecular design for emerging technologies
Mather, B. D., Viswanathan, K., Miller, K. M., & Long, T. E. (2006) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2006.03.001 · Cited by 1,127
Nucleophilic Phosphine Organocatalysis
Methot, J. L., & Roush, W. R. (2004) · Advanced Synthesis & Catalysis · doi:10.1002/adsc.200404087 · Cited by 983
Robust, Efficient, and Orthogonal Synthesis of Dendrimers via Thiol-ene “Click” Chemistry
Killops, K. L., Campos, L. M., & Hawker, C. J. (2008) · Journal of the American Chemical Society · doi:10.1021/ja8006325 · Cited by 792
The Emergence of Thiol–Ene Coupling as a Click Process for Materials and Bioorganic Chemistry
Dondoni, A. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200802516 · Cited by 619
The oxa-Michael reaction: from recent developments to applications in natural product synthesis
Nising, C. F., & Bräse, S. (2008) · Chemical Society Reviews · doi:10.1039/b718357g · Cited by 467
Elbert, D. L., & Hubbell, J. A. (2001) · Biomacromolecules · doi:10.1021/bm0056299 · Cited by 409
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The Thiol-Michael Addition Click Reaction: A Powerful and Widely Used Tool in Materials Chemistry
Nair, D. P., Podgórski, M., Chatani, S., Gong, T., Xi, W., Fenoli, C. R., & Bowman, C. N. (2014) · Chemistry of Materials · doi:10.1021/cm402180t · Cited by 1,596
Lowe, A. B. (2014) · Polym. Chem. · doi:10.1039/c4py00339j · Cited by 768
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Click Chemistry in Materials Science
Xi, W., Scott, T. F., Kloxin, C. J., & Bowman, C. N. (2014) · Advanced Functional Materials · doi:10.1002/adfm.201302847 · Cited by 677
Liquid crystal elastomers: an introduction and review of emerging technologies
Ula, S. W., Traugutt, N. A., Volpe, R. H., Patel, R. R., Yu, K., & Yakacki, C. M. (2018) · Liquid Crystals Reviews · doi:10.1080/21680396.2018.1530155 · Cited by 316
Click chemistry strategies for the accelerated synthesis of functional macromolecules
Geng, Z., Shin, J. J., Xi, Y., & Hawker, C. J. (2021) · Journal of Polymer Science · doi:10.1002/pol.20210126 · Cited by 269
Synthetic dynamic hydrogels promote degradation-independent in vitro organogenesis
Chrisnandy, A., Blondel, D., Rezakhani, S., Broguiere, N., & Lutolf, M. P. (2022) · Nature Materials · doi:10.1038/s41563-021-01136-7 · Cited by 237
Two‐Stage Reactive Polymer Network Forming Systems
Nair, D. P., Cramer, N. B., Gaipa, J. C., McBride, M. K., Matherly, E. M., McLeod, R. R., Shandas, R., & Bowman, C. N. (2012) · Advanced Functional Materials · doi:10.1002/adfm.201102742 · Cited by 166
Metadata
- Authors
- Chan, J. W., Hoyle, C. E., Lowe, A. B., & Bowman, M.
- Venue
- Macromolecules
- Publisher
- American Chemical Society (ACS)
- Published
- 2010-07-14
- Volume
- 43
- Issue
- 15
- Pages
- 6381-6388
- ISSN
- 0024-9297 (ISSN-L)
- 1520-5835
- OpenAlex
- W1978854006
- Cited by
- 383
- References
- 30
- FWCI
- 10.73
- Type
- journal article
- Language
- en
- Open access
- closed
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