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      Click Nucleophilic Conjugate Additions to Activated Alkynes: Exploring Thiol-yne, Amino-yne, and Hydroxyl-yne Reactions from (Bio)Organic to Polymer Chemistry

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          Abstract

          The 1,4-conjugate addition reaction between activated alkynes or acetylenic Michael acceptors and nucleophiles ( i.e., the nucleophilic Michael reaction) is a historically useful organic transformation. Despite its general utility, the efficiency and outcomes can vary widely and are often closely dependent upon specific reaction conditions. Nevertheless, with improvements in reaction design, including catalyst development and an expansion of the substrate scope to feature more electrophilic alkynes, many examples now present with features that are congruent with Click chemistry. Although several nucleophilic species can participate in these conjugate additions, ubiquitous nucleophiles such as thiols, amines, and alcohols are commonly employed and, consequently, among the most well developed. For many years, these conjugate additions were largely relegated to organic chemistry, but in the last few decades their use has expanded into other spheres such as bioorganic chemistry and polymer chemistry. Within these fields, they have been particularly useful for bioconjugation reactions and step-growth polymerizations, respectively, due to their excellent efficiency, orthogonality, and ambient reactivity. The reaction is expected to feature in increasingly divergent application settings as it continues to emerge as a Click reaction.

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          Thiol-ene click chemistry.

          Following Sharpless' visionary characterization of several idealized reactions as click reactions, the materials science and synthetic chemistry communities have pursued numerous routes toward the identification and implementation of these click reactions. Herein, we review the radical-mediated thiol-ene reaction as one such click reaction. This reaction has all the desirable features of a click reaction, being highly efficient, simple to execute with no side products and proceeding rapidly to high yield. Further, the thiol-ene reaction is most frequently photoinitiated, particularly for photopolymerizations resulting in highly uniform polymer networks, promoting unique capabilities related to spatial and temporal control of the click reaction. The reaction mechanism and its implementation in various synthetic methodologies, biofunctionalization, surface and polymer modification, and polymerization are all reviewed.
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            Click Chemistry: Diverse Chemical Function from a Few Good Reactions

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              Recent advances in dynamic covalent chemistry.

              Dynamic covalent chemistry (DCvC) has been strongly integrated into diverse research fields, and has enabled easy access to a variety of combinatorial libraries, 2-D macrocycles, and 3-D molecular cages that target many important applications, such as drug discovery, biotechnology, molecular separation, light harvesting, etc. DCvC relies on the reversible formation and breaking of rather strong covalent bonding within molecules. Therefore it combines the error-correction capability of supramolecular chemistry and the robustness of covalent bonding. Compared to those supramolecular interactions, dynamic covalent reactions usually have slower kinetics and require the assistance of catalysts to achieve rapid equilibrium. Although the scope of dynamic covalent reactions is rapidly expanding, the reversible reactions suitable for DCvC are still very limited. The identification and development of new dynamic reactions and catalysts would be critical for the further advancement of DCvC. This review covers the recent development of dynamic covalent reactions as well as their applications.
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                Author and article information

                Journal
                Chem Rev
                Chem Rev
                cr
                chreay
                Chemical Reviews
                American Chemical Society
                0009-2665
                1520-6890
                25 March 2021
                23 June 2021
                : 121
                : 12 , Click Chemistry
                : 6744-6776
                Affiliations
                [§ ]School of Chemistry, University of Birmingham , Edgbaston, Birmingham B15 2TT, U.K.
                Author notes
                [* ]A.P.D.: email, a.dove@ 123456bham.ac.uk .
                [* ]J.C.W.: email, j.worch@ 123456bham.ac.uk .
                Author information
                http://orcid.org/0000-0002-4354-8303
                http://orcid.org/0000-0001-8208-9309
                Article
                10.1021/acs.chemrev.0c01076
                8227514
                33764739
                2fb44991-0af5-4e8c-9e8e-8268d86e2143
                © 2021 American Chemical Society

                Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works ( https://creativecommons.org/licenses/by-nc-nd/4.0/).

                History
                : 02 October 2020
                Funding
                Funded by: H2020 European Research Council, doi 10.13039/100010663;
                Award ID: 681559
                Funded by: University of Birmingham, doi 10.13039/501100000855;
                Award ID: NA
                Categories
                Review
                Custom metadata
                cr0c01076
                cr0c01076

                Chemistry
                Chemistry

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