Study and application of noncatalyzed photoinduced conjugation of azides and cycloocta-1,2,3-selenadiazoles

Jedinakova, P.; Šebej, Peter; Slanina, Tomáš; Klán, Petr; Hlaváč, Jan

doi:10.1039/c6cc01789d

Cited by 7 publications

(2 citation statements)

References 44 publications

(47 reference statements)

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“…Jedinaḱováet al have reported photoSPAAC reactions via the synthesis of cyclooctynes via the photodecomposition of cycloota-1,2,3-selenadiazole (Figure 22). 79 This reaction, however, exhibits a relatively poor quantum yield. Moreover, although selenium is an essential nutrient, in elevated concentrations it may have unpleasant or toxic physiological effects, making the broader application of its use in click reactions problematic.…”

Section: Dipolar Cycloadditionsmentioning

confidence: 99%

Photoclick Chemistry: A Bright Idea

et al. 2021

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At its basic conceptualization, photoclick chemistry embodies a collection of click reactions that are performed via the application of light. The emergence of this concept has had diverse impact over a broad range of chemical and biological research due to the spatiotemporal control, high selectivity, and excellent product yields afforded by the combination of light and click chemistry. While the reactions designated as “photoclick” have many important features in common, each has its own particular combination of advantages and shortcomings. A more extensive realization of the potential of this chemistry requires a broader understanding of the physical and chemical characteristics of the specific reactions. This review discusses the features of the most frequently employed photoclick reactions reported in the literature: photomediated azide–alkyne cycloadditions, other 1,3-dipolarcycloadditions, Diels–Alder and inverse electron demand Diels–Alder additions, radical alternating addition chain transfer additions, and nucleophilic additions. Applications of these reactions in a variety of chemical syntheses, materials chemistry, and biological contexts are surveyed, with particular attention paid to the respective strengths and limitations of each reaction and how that reaction benefits from its combination with light. Finally, challenges to broader employment of these reactions are discussed, along with strategies and opportunities to mitigate such obstacles.

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Section: Dipolar Cycloadditionsmentioning

confidence: 99%

Photoclick Chemistry: A Bright Idea

et al. 2021

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“…Jedináková et al reported the formation of cyclooctynes via the decomposition of cycloota‐1,2,3‐selenadiazole in presence of light (Scheme 7). [61] The cyclooctyne generated was rapidly captured with various azides. One of the disadvantages of this strategy is the use of selenium which can be toxic when used in higher concentrations like copper metal.…”

Section: Introductionmentioning

confidence: 99%

Click Chemistry Mediated by Photochemical Energy

Arora

Singh

2022

ChemistrySelect

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Light mediated chemical reactions have emerged as an important class of reactions known as photoclick reactions. These reactions have allowed synthesis of complex molecular structures to be performed under mild conditions. The spatiotemporal control offered by photoclick reactions cannot be achieved by thermal processes. This review captures the advances in the area of photoclick chemistry and highlights the importance of light induced cycloaddition reactions, thiol‐ene/yne reactions and hetero‐Diels–Alder reactions.

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