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      Green Methodologies for Copper(I)-Catalyzed Azide-Alkyne Cycloadditions: A Comparative Study

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          Abstract

          Successful copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions may be achieved by several methods. In this paper, four synthetic protocols were performed for direct comparison of time required for the synthesis, yield, and purity of the 1 H-1,2,3-triazole products. The methods with Cu(I) catalysts were conventional, microwave heating, solvent-free, and a method using glycerol solvent. The compounds synthesized in this paper were known non-fluorinated triazoles and new fluorinated triazoles. The results lead to the conclusion that the microwave method should be strongly considered for CuAAC syntheses.

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          A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction.

          Prasad Appukkuttan, Wim Dehaen, Valery V Fokin … (2004)
          A microwave-assisted three-component reaction was used to prepare a series of 1,4-disubstituted-1,2,3-triazoles from corresponding alkyl halides, sodium azide, and alkynes. This procedure eliminates the need to handle organic azides, as they are generated in situ, making this already powerful click process even more user-friendly and safe.
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            Copper-catalysed azide-alkyne cycloadditions (CuAAC): an update.

            Estela Haldón, M Nicasio, Pedro Pérez-Moreno (2015)
            The reactions of organic azides and alkynes catalysed by copper species represent the prototypical examples of click chemistry. The so-called CuAAC reaction (copper-catalysed azide-alkyne cycloaddition), discovered in 2002, has been expanded since then to become an excellent tool in organic synthesis. In this contribution the recent results described in the literature since 2010 are reviewed, classified according to the nature of the catalyst precursor: copper(I) or copper(II) salts or complexes, metallic or nano-particulated copper and several solid-supported copper systems.
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              Click chemistry under non-classical reaction conditions.

              C. Oliver Kappe, Henriëtte E. van der Horst (2010)
              First described almost a decade ago, "click" reactions such as the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) are widely used today in organic and medicinal chemistry, in the polymer and material science field, and in chemical biology. While most click reactions can be performed at room temperature there are instances where some form of process intensification is required. In this tutorial review, aimed at the synthetic chemistry community, examples of click chemistry carried out under non-classical reaction conditions, such as for example applying microwave heating or continuous flow processing will be highlighted.
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                Author and article information

                Contributors
                John Spencer: Role: Academic Editor
                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 10 March 2019
                Publication date Collection: March 2019
                Volume: 24
                Issue: 5
                Electronic Location Identifier: 973
                Affiliations
                Department of Chemistry and Biochemistry, University of Colorado Colorado Springs, Colorado Springs, CO 80918, USA; mtrujil3@ 123456uccs.edu (M.T.); chullcre@ 123456uccs.edu (C.H.-C.); aoutlaw4@ 123456uccs.edu (A.O.); kstewar4@ 123456uccs.edu (K.S.); ltaylor6@ 123456uccs.edu (L.T.); lgeorge@ 123456uccs.edu (L.G.); allison.duensing@ 123456ucdenver.edu (A.D.); breanna.tracey@ 123456outlook.com (B.T.)
                Author notes
                [* ]Correspondence: aschoffs@ 123456uccs.edu ; Tel.: +1-719-255-3163; Fax: +1-719-255-5205
                Author information
                https://orcid.org/0000-0002-7863-6768
                https://orcid.org/0000-0001-8821-7869
                Article
                Publisher ID: molecules-24-00973
                DOI: 10.3390/molecules24050973
                PMC ID: 6429464
                PubMed ID: 30857343
                SO-VID: 93eb8887-0e69-4e84-8242-df98b21aaf00
                Copyright © © 2019 by the authors.
                License:

                Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license ( http://creativecommons.org/licenses/by/4.0/).

                History
                Date received : 01 February 2019
                Date accepted : 01 March 2019
                Categories
                Subject: Article

                Keywords: 1h-1,2,3-triazole,copper-catalyzed azide-alkyne cycloaddition (cuaac),microwave heating,solvent-free reaction,green chemistry,fluorotriazole
                Data availability:
                Keywords: 1h-1,2,3-triazole, copper-catalyzed azide-alkyne cycloaddition (cuaac), microwave heating, solvent-free reaction, green chemistry, fluorotriazole

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