Poly(allyl alcohol) Homo- and Block Polymers by Postpolymerization Reduction of an Activated Polyacrylamide

Larsen, Michael B.; Wang, Shao Jie

doi:10.1021/jacs.8b07542

Cited by 38 publications

(34 citation statements)

References 45 publications

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“…Furthermore, new types of materials could be obtained from these known polymers through post-polymerization modifications. In fact, the synthesis of high molar mass poly(allyl alcohol) polymers has been recently investigated using polyacrylamide reduction with borohydrides 169 . The development of active catalytic systems to afford the hydrogenative version of this reaction could be one of the most interesting future applications in the amide hydrogenation area.…”

Section: Future Perspectivesmentioning

confidence: 99%

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

et al. 2020

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Catalytic hydrogenation of amides is of great interest for chemists working in organic synthesis, as the resulting amines are widely featured in natural products, drugs, agrochemicals, dyes, etc. Compared to traditional reduction of amides using (over)stoichiometric reductants, the direct hydrogenation of amides using molecular hydrogen represents a greener approach. Furthermore, amide hydrogenation is a highly versatile transformation, since not only higher amines (obtained by CO cleavage), but also lower amines and alcohols, or amino alcohols (obtained by C-N cleavage) can be selectively accessed by fine tuning of reaction conditions. This review describes the most recent advances in the area of amide hydrogenation using H 2 exclusively and molecularly defined homogeneous as well as nanostructured heterogeneous catalysts, with a special focus on catalyst development and synthetic applications. T he development of green and sustainable methods is a central focus of modern organic synthesis and its applications in various areas of the chemical industry. In this respect, many reduction reactions, traditionally employing stoichiometric amounts of metal hydrides with inherent low atom efficiency 1 , can be favorably replaced by catalytic hydrogenations. In fact, the combination of molecular hydrogen and catalysts does not only allow avoiding formation of waste products 2 , it also opens the door to clean transformations based on renewable energies as the conversion of solar or wind energy to "green" hydrogen is likely to be implemented in the coming years. Among the many reduction reactions known, amide hydrogenation can be encountered as one of the most desired considering the importance of the derived amines in several branches of chemical industry. In fact, since the start of the Green Chemistry Institute Pharmaceutical Roundtable in the United States in 2005, several projects aimed to the achievement of a practical amide hydrogenation methodology have been supported 3,4. The long-term interest of the pharmaceutical industry in this specific transformation is explained by the fact that it ideally affords structurally complex amines, present in many of the currently employed drugs. Furthermore, amines are also in bulk and fine chemicals used in the manufacture of plastics, textiles, surfactants, dyes, and many more 5. Amides play a central role in the chemistry of life, as they are the key elements to generate peptides and proteins from amino acid monomers. At the same time, they are present in artificial

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Section: Future Perspectivesmentioning

confidence: 99%

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

et al. 2020

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“…[70] Typically, transamidations with electron-deficient heterocyclic amines, such as in Figure 2, are particularly challenging due to low nucleophilicity and the potential to undergo side reactions of the heterocyclic ring. [40][41][42][43][44][45][46][47][48][49][50] As such, we were delighted to find that a remarkably broad range of heterocyclic amines,…”

Section: Resultsmentioning

confidence: 99%

Chemoselective Transamidation of Thioamides by Transition‐Metal‐Free N−C(S) Transacylation

Xing

Zhao

et al. 2022

Angewandte Chemie

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Thioamides represent highly valuable isosteric in the strictest sense “single‐atom substitution” analogues of amides that have found broad applications in chemistry and biology. A long‐standing challenge is the direct transamidation of thioamides, a process which would convert one thioamide bond (R−C(S)−NR1R2) into another (R−C(S)−NR3N4). Herein, we report the first general method for the direct transamidation of thioamides by highly chemoselective N−C(S) transacylation. The method relies on site‐selective N‐tert‐butoxycarbonyl activation of 2° and 1° thioamides, resulting in ground‐state‐destabilization of thioamides, thus enabling to rationally manipulate nucleophilic addition to the thioamide bond. This method showcases a remarkably broad scope including late‐stage functionalization (>100 examples). We further present extensive DFT studies that provide insight into the chemoselectivity and provide guidelines for the development of transamidation methods of the thioamide bond.

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“…Thus, PPM often reduces the number of synthetic steps required for material syntheses and provides precursor materials that can be modified with a wide variety of functional groups. [5][6][7][8][9][10][11][12][13][14][15] For nanomaterials, reactive functionality provides a convenient and polyvalent means of introducing valuable moieties such as dyes, [16][17][18] catalysts or drugs. 19 PPM can also be employed to dynamically modify nanostructure properties, endowing such constructs with the capability to respond to environmental stimuli.…”

Section: Introductionmentioning

confidence: 99%

Functional nanostructures by NiCCo-PISA of helical poly(aryl isocyanide) copolymers

et al. 2021

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Poly(allyl alcohol) Homo- and Block Polymers by Postpolymerization Reduction of an Activated Polyacrylamide

Cited by 38 publications

References 45 publications

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

Homogeneous and heterogeneous catalytic reduction of amides and related compounds using molecular hydrogen

Chemoselective Transamidation of Thioamides by Transition‐Metal‐Free N−C(S) Transacylation

Functional nanostructures by NiCCo-PISA of helical poly(aryl isocyanide) copolymers

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