Iridium‐Catalyzed Hydroxyl‐Enabled Cycloaddition of Azides and Alkynes

Chen, Renjie; Zeng, Lieguang; Lai, Zhencheng; Cui, Sunliang

doi:10.1002/adsc.201801410

Cited by 37 publications

(23 citation statements)

References 74 publications

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“…In both cases, the reactions are fully regioselective, but mm concentrations of the reagents are required,w hich so far limits their use for chemical and cell biology applications. [44]…”

Section: Copper(i)-promoted Azide-alkyne Cycloaddition (Cuaac)mentioning

confidence: 99%

Transition Metal‐Promoted Reactions in Aqueous Media and Biological Settings

Destito

Vidal

López

et al. 2021

Chemistry A European J

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During the last decade, there has been a tremendous interest for developing non‐natural biocompatible transformations in biologically relevant media. Among the different encountered strategies, the use of transition metal complexes offers unique possibilities due to their high transformative power. However, translating the potential of metal catalysts to biological settings, including living cells or small‐animal models such as mice or zebrafish, poses numerous challenges associated to their biocompatibility, and their stability and reactivity in crowded aqueous environments. Herein, we describe the most relevant advances in this direction, with a particular emphasis on the systems’ structure, their mode of action and the mechanistic bases of each transformation. Thus, the key challenges from an organometallic perspective might be more easily identified.

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“…In both cases, the reactions are fully regioselective, but mm concentrations of the reagents are required,w hich so far limits their use for chemical and cell biology applications. [44]…”

Section: Copper(i)-promoted Azide-alkyne Cycloaddition (Cuaac)mentioning

confidence: 99%

Transition Metal‐Promoted Reactions in Aqueous Media and Biological Settings

Destito

Vidal

López

et al. 2021

Chemistry A European J

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“…[39] In 2019, Cui and coworkers demonstrated that by introducing an ortho hydroxyl group into the aryl ring, IrAAC reactions of them were enormously promoted, regioselectively affording trisubstituted triazoles 56 in up to 96% yield (Scheme 29). [46] Since the C � C Cui et al reported that IrAAC is suitable for 1-alkynyltriazenes 57 as well, in which the triazenyl group is thought to be crucial in determining the regioselectivity (Scheme 30). [47] Notably, the formed 5-triazenyltriazoles 58 could be easily converted into 5-amino triazoles 59, which could be further decorated to provide a variety of functionalized triazoles (60-62 for instance).…”

Section: Ira I Acmentioning

confidence: 99%

“…[42,52] Cui et al reported the RhAAC reaction of 2-(phenylethynyl)phenol to afford triazole 73 with absolute regiocontrol (Scheme 34b). [46] Related plausible mechanisms to elucidate the regiocontrol in above cases were shown in Scheme 35. The electronic effect- From the cases listed in this section we can see that both the alkyne scope and mechanism of RhA I AC are similar to IrA I AC.…”

Section: Rha I Acmentioning

confidence: 99%

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Transition Metal‐Catalyzed Cycloaddition of Azides with Internal Alkynes

Ding

2020

Asian J Org Chem

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Metal-catalyzed azide-alkyne cycloaddition reactions represent the most convenient and atom-economic way to construct robust 1,2,3-triazole units. Remarkable copperand ruthenium-based catalytic systems have been well established for regioselective preparation of 1,4-and 1,5disubstituted 1,2,3-triazoles, both of which have been widely utilized in various areas. In comparison, exploitation of efficient methods to promote the cycloaddition of azides with internal alkynes to afford 1,4,5-trisubstituted 1,2,3triazole motifs with high regioselectivity is still challenging and attractive. This review provides a thorough summary of the developments in metal-catalyzed cycloaddition of azides with internal alkynes. Besides discussions about mechanism and scope, applications of these strategies were also briefly overviewed.

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“…The same catalytic system also works for the C-S coupling of aryl halides and sulfinate salts. [68] Scheme 29. Thioetherification via EDA complex formation.…”

Section: Electron Donor-acceptor Complexesmentioning

confidence: 99%

Photochemical Strategies for Carbon–Heteroatom Bond Formation

2019

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Photochemistry enables new synthetic means to form carbon–heteroatom bonds. Photocatalysts can catalyze carbon–heteroatom cross‐couplings by electron or energy transfer either alone or in combination with a second catalyst. Photocatalyst‐free methods are possible using photolabile substrates or by generating photoactive electron donor‐acceptor complexes. This review summarizes and discusses the strategies used in light‐mediated carbon–heteroatom bond formations based on the proposed mechanisms.

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Iridium‐Catalyzed Hydroxyl‐Enabled Cycloaddition of Azides and Alkynes

Cited by 37 publications

References 74 publications

Transition Metal‐Promoted Reactions in Aqueous Media and Biological Settings

Transition Metal‐Promoted Reactions in Aqueous Media and Biological Settings

Transition Metal‐Catalyzed Cycloaddition of Azides with Internal Alkynes

Photochemical Strategies for Carbon–Heteroatom Bond Formation

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