Iodine Azide

Häßner, Alfred; Marinescu, Lavinia; Bols, Mikael

doi:10.1002/047084289x.ri007

Cited by 4 publications

(3 citation statements)

References 64 publications

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“…Azide groups can be introduced at reactive graphitic edges through a Hassner-type addition of IN 3 generated in situ, followed by surface rearomatization through elimination of HI (Figure d) . The azide-functionalized surface can subsequently react with alkyne derivatives via 1,3-dipolar cycloaddition “click” chemistry to link a molecular catalyst. − In addition to the approaches listed above, there have also been reports of other methods involving the addition of carbenes , or nitrenes, cyclopropanation, and Diels–Alder addition, which can functionalize a variety of carbon material surfaces.…”

Section: Immobilization Strategies For Molecular Catalystsmentioning

confidence: 99%

Electro- and Solar-Driven Fuel Synthesis with First Row Transition Metal Complexes

et al. 2019

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The synthesis of renewable fuels from abundant water or the greenhouse gas CO 2 is a major step toward creating sustainable and scalable energy storage technologies. In the last few decades, much attention has focused on the development of nonprecious metal-based catalysts and, in more recent years, their integration in solid-state support materials and devices that operate in water. This review surveys the literature on 3d metal-based molecular catalysts and focuses on their immobilization on heterogeneous solid-state supports for electro-, photo-, and photoelectrocatalytic synthesis of fuels in aqueous media. The first sections highlight benchmark homogeneous systems using proton and CO 2 reducing 3d transition metal catalysts as well as commonly employed methods for catalyst immobilization, including a discussion of supporting materials and anchoring groups. The subsequent sections elaborate on productive associations between molecular catalysts and a wide range of substrates based on carbon, quantum dots, metal oxide surfaces, and semiconductors. The molecule–material hybrid systems are organized as “dark” cathodes, colloidal photocatalysts, and photocathodes, and their figures of merit are discussed alongside system stability and catalyst integrity. The final section extends the scope of this review to prospects and challenges in targeting catalysis beyond “classical” H 2 evolution and CO 2 reduction to C 1 products, by summarizing cases for higher-value products from N 2 reduction, C x >1 products from CO 2 utilization, and other reductive organic transformations.

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Section: Immobilization Strategies For Molecular Catalystsmentioning

confidence: 99%

Electro- and Solar-Driven Fuel Synthesis with First Row Transition Metal Complexes

et al. 2019

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“…The azide radical, which was an electron-deficient N -centered radical, was proved to be an efficient hydrogen-abstracting species in C(sp 3 )–H bond functionalization 18 and plays versatile roles in different transformations. 17–19 Hence, we attempted to use the azide radical to abstract more electron-rich N -α-C–H bonds to realize selective oxidation reaction of amides. 20 At the very beginning, we tried to utilize NIS and azide to synthesize the highly reactive reagent IN 3 in situ , 19 e initiating amide oxidative desaturation via a radical process.…”

Section: Resultsmentioning

confidence: 99%

Selective desaturation of amides: a direct approach to enamides

Cheng

Liu

et al. 2022

Chem. Sci.

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“…For the 1,2-elimination approach, the method developed by Hassner, , whereas an iodoazidation of alkenes using iodine azide is followed by a base-promoted elimination of HI, is often employed due to its succinct nature (Scheme B-3). However, this method is not ideal as IN 3 , despite in situ generated, is still a safety concern due to its explosive nature, the strongly oxidative/electrophilic nature of the conditions including the use of ICl significantly limits the scope of tolerable functional groups, and with internal alkene substrates regioselectivity can be an issue. For the hydroboration/oxidative azidation approach, the reaction requires excess of Cu(II) salt, uses unstable and freshly prepared Sia 2 BH, and leads to formally anti-Markovnikov syn addion of HN 3 , and the symmetric case shown in Scheme B-4 is the only reported internal alkyne example.…”

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confidence: 99%

Ligand-Accelerated Gold-Catalyzed Addition of in Situ Generated Hydrazoic Acid to Alkynes under Neat Conditions

Liao

Wang

et al. 2017

Org. Lett.

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The direct addition of in situ generated hydrazoic acid to alkynes is realized without solvent by using a gold catalyst derived from a recently designed remotely functionalized biaryl-2-ylphosphine ligand (i.e., WangPhos). With terminal alkynes, the additions are mostly realized with 0.1 mol% catalyst loadings and at 40 °C. With more challenging internal alkynes devoid of direct EWG substitution, the one-step transformation is realized for the first time with generally high efficiency at ambient temperature.

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Iodine Azide

Cited by 4 publications

References 64 publications

Electro- and Solar-Driven Fuel Synthesis with First Row Transition Metal Complexes

Electro- and Solar-Driven Fuel Synthesis with First Row Transition Metal Complexes

Selective desaturation of amides: a direct approach to enamides

Ligand-Accelerated Gold-Catalyzed Addition of in Situ Generated Hydrazoic Acid to Alkynes under Neat Conditions

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