Abstract
Noncatalyzed cycloadditions between strained alkynes or alkenes and 1,3-dipoles or dienes (copper-free click reactions) have emerged as powerful bioorthogonal transformations. Biomolecule labeling strategies based on applications of strain-promoted cycloaddition continue to garner considerable interest, and this chemistry is poised for rapid growth in the future. Metal-free click chemistry is also ideally suited to facilitate assembly or modification of functional materials, and so its use in materials chemistry is also expected to expand. This review examines the reactivity of the most common Cu-free click reagents currently employed: cyclooctynes, E-cyclooctenes, norbornenes, and cyclopropenes. Factors important in governing the reactivity of these strained π systems and approaches toward increasing the ability of these reagents to engage in spontaneous and selective cycloadditions with complementary dipoles/dienes are discussed.
Keywords: Copper-free click, azide-alkyne cycloaddition, inverse electron demand cycloaddition, strain-promoted cycloaddition, cyclooctyne, trans-cyclooctene, tetrazine, cyclopropene.
Current Organic Chemistry
Title:Strain-Promoted Cycloadditions for Development of Copper-Free Click Reactions
Volume: 20 Issue: 18
Author(s): F. Christopher Pigge
Affiliation:
Keywords: Copper-free click, azide-alkyne cycloaddition, inverse electron demand cycloaddition, strain-promoted cycloaddition, cyclooctyne, trans-cyclooctene, tetrazine, cyclopropene.
Abstract: Noncatalyzed cycloadditions between strained alkynes or alkenes and 1,3-dipoles or dienes (copper-free click reactions) have emerged as powerful bioorthogonal transformations. Biomolecule labeling strategies based on applications of strain-promoted cycloaddition continue to garner considerable interest, and this chemistry is poised for rapid growth in the future. Metal-free click chemistry is also ideally suited to facilitate assembly or modification of functional materials, and so its use in materials chemistry is also expected to expand. This review examines the reactivity of the most common Cu-free click reagents currently employed: cyclooctynes, E-cyclooctenes, norbornenes, and cyclopropenes. Factors important in governing the reactivity of these strained π systems and approaches toward increasing the ability of these reagents to engage in spontaneous and selective cycloadditions with complementary dipoles/dienes are discussed.
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Cite this article as:
Pigge F. Christopher, Strain-Promoted Cycloadditions for Development of Copper-Free Click Reactions, Current Organic Chemistry 2016; 20 (18) . https://dx.doi.org/10.2174/1385272820666160402002408
DOI https://dx.doi.org/10.2174/1385272820666160402002408 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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