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Relevant bibliographies by topics / Catalyzed Transamidation

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Academic literature on the topic 'Catalyzed Transamidation'

Author: Grafiati

Published: 18 May 2024

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Journal articles on the topic "Catalyzed Transamidation"

1

Laclef, Sylvain, Maria Kolympadi Marković, and Dean Marković. "Amide Synthesis by Transamidation of Primary Carboxamides." Synthesis 52, no. 21 (June 4, 2020): 3231–42. http://dx.doi.org/10.1055/s-0040-1707133.

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The amide functionality is one of the most important and widely used groups in nature and in medicinal and industrial chemistry. Because of its importance and as the actual synthetic methods suffer from major drawbacks, such as the use of a stoichiometric amount of an activating agent, epimerization and low atom economy, the development of new and efficient amide bond forming reactions is needed. A number of greener and more effective strategies have been studied and developed. The transamidation of primary amides is particularly attractive in terms of atom economy and as ammonia is the single byproduct. This review summarizes the advancements in metal-catalyzed and organocatalyzed transamidation methods. Lewis and Brønsted acid transamidation catalysts are reviewed as a separate group. The activation of primary amides by promoter, as well as catalyst- and promoter-free protocols, are also described. The proposed mechanisms and key intermediates of the depicted transamidation reactions are shown.1 Introduction2 Metal-Catalyzed Transamidations3 Organocatalyzed Transamidations4 Lewis and Brønsted Acid Catalysis5 Promoted Transamidation of Primary Amides6 Catalyst- and Promoter-Free Protocols7 Conclusion

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2

Chandrasekaran, Srinivasan, and Rajagopal Ramkumar. "Catalyst-Free, Metal-Free, and Chemoselective Transamidation of Activated Secondary Amides." Synthesis 51, no. 04 (October 18, 2018): 921–32. http://dx.doi.org/10.1055/s-0037-1610664.

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A simple protocol, which is catalyst-free, metal-free, and chemoselective, for transamidation of activated secondary amides in ethanol as solvent under mild conditions is reported. A wide range of amines, amino acids, amino alcohols, and the substituents, which are problematic in catalyzed transamidation, are tolerated in this methodology. The transamidation reaction was successfully extended to water as the medium as well. The present methodology appears to be better than the other catalyzed transamidations reported recently.

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3

Szostak, Michal, and Guangchen Li. "Non-Classical Amide Bond Formation: Transamidation and Amidation of Activated Amides and Esters by Selective N–C/O–C Cleavage." Synthesis 52, no. 18 (May 15, 2020): 2579–99. http://dx.doi.org/10.1055/s-0040-1707101.

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In the past several years, tremendous advances have been made in non-classical routes for amide bond formation that involve transamidation and amidation reactions of activated amides and esters. These new methods enable the formation of extremely valuable amide bonds via transition-metal-catalyzed, transition-metal-free, or metal-free pathways by exploiting chemoselective acyl C–X (X = N, O) cleavage under mild conditions. In a broadest sense, these reactions overcome the formidable challenge of activating C–N/C–O bonds of amides or esters by rationally tackling nN → π*C=O delocalization in amides and nO → π*C=O donation in esters. In this account, we summarize the recent remarkable advances in the development of new methods for the synthesis of amides with a focus on (1) transition-metal/NHC-catalyzed C–N/C–O bond activation, (2) transition-metal-free highly selective cleavage of C–N/C–O bonds, (3) the development of new acyl-transfer reagents, and (4) other emerging methods.1 Introduction2 Transamidation of Amides2.1 Transamidation by Metal–NHC Catalysis (Pd–NHC, Ni–NHC)2.2 Transition-Metal-Free Transamidation via Tetrahedral Intermediates2.3 Reductive Transamidation2.4 New Acyl-Transfer Reagents2.5 Tandem Transamidations3 Amidation of Esters3.1 Amidation of Esters by Metal–NHC Catalysis (Pd–NHC, Ni–NHC)3.2 Transition-Metal-Free Amidation of Esters via Tetrahedral Intermediates3.3 Reductive Amidation of Esters4 Transamidations of Amides by Other Mechanisms5 Conclusions and Outlook

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4

Rachel, N. M., and J. N. Pelletier. "One-pot peptide and protein conjugation: a combination of enzymatic transamidation and click chemistry." Chemical Communications 52, no. 12 (2016): 2541–44. http://dx.doi.org/10.1039/c5cc09163b.

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5

Sharma, Manu, Harikrishnan K, Umesh Kumar Gaur, and Ashok K. Ganguli. "Synthesis of mesoporous SiO₂–CeO₂ hybrid nanostructures with high catalytic activity for transamidation reaction." RSC Advances 13, no. 19 (2023): 13134–41. http://dx.doi.org/10.1039/d3ra01552a.

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6

Dander, Jacob E., Emma L. Baker, and Neil K. Garg. "Nickel-catalyzed transamidation of aliphatic amide derivatives." Chemical Science 8, no. 9 (2017): 6433–38. http://dx.doi.org/10.1039/c7sc01980g.

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7

Yang, Dahyeon, Taeil Shin, Hyunwoo Kim, and Sunwoo Lee. "Nickel/briphos-catalyzed transamidation of unactivated tertiary amides." Organic & Biomolecular Chemistry 18, no. 31 (2020): 6053–57. http://dx.doi.org/10.1039/d0ob01271h.

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8

Ojeda-Porras, Andrea, and Diego Gamba-Sánchez. "Transamidation of thioacetamide catalyzed by SbCl3." Tetrahedron Letters 56, no. 29 (July 2015): 4308–11. http://dx.doi.org/10.1016/j.tetlet.2015.05.067.

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9

Yedage, Subhash L., Denvert S. D'silva, and Bhalchandra M. Bhanage. "MnO2 catalyzed formylation of amines and transamidation of amides under solvent-free conditions." RSC Advances 5, no. 98 (2015): 80441–49. http://dx.doi.org/10.1039/c5ra13094h.

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10

Arefi, Marzban, and Akbar Heydari. "Transamidation of primary carboxamides, phthalimide, urea and thiourea with amines using Fe(OH)3@Fe3O4 magnetic nanoparticles as an efficient recyclable catalyst." RSC Advances 6, no. 29 (2016): 24684–89. http://dx.doi.org/10.1039/c5ra27680b.

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Dissertations / Theses on the topic "Catalyzed Transamidation"

1

Bhattacharya, Suchandra. "New catalytic applications of functionalized graphenes and metal embedded organic polymer." Thesis, University of North Bengal, 2020. http://ir.nbu.ac.in/handle/123456789/4363.

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Atkinson, Benjamin. "Metal catalysed acyl transfer reactions of amides." Thesis, University of Bath, 2015. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.665412.

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The following thesis outlines work carried out during the last three years for the development and investigation of methodologies using amides as N- and O- acylating agents. Chapter 1 highlights the range of methodologies and protocols reported in the literature that use amides as precursors for the synthesis of both functionalised amides and esters. The introduction will highlight the range of catalysts and promoters used as well as the scope of the current methodologies. As well as this it will highlight the limitations of the methodologies so emphasising where the following research fits into these areas. Chapter 2 presents the development of a transamidation methodology using zirconocene dichloride as a catalyst. The scope with respect to functional group tolerance is presented as well as the investigations into the mechanism of the reaction. Chapter 3 builds on the research presented in Chapter 2 and details the development of a more catalytically active zirconocene transamidation methodology. By the addition of a catalytic additive the temperature or time required for the reaction to be carried out could be lowered. Investigations into the mechanism were also carried out highlighting the in situ formation of an active catalytic species. Chapter 4 details the development of an operationally simple methodology for the O-acylation of alcohols using amides. Using a catalytic amount scandium triflate the substrate scope of the reaction was explored with a proposed mechanism presented based on activation of the amide.

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Book chapters on the topic "Catalyzed Transamidation"

1

Rao, Sadu Nageswara, Darapaneni Chandra Mohan, and Subbarayappa Adimurthy. "L-Proline Catalyzed Transamidation of Thioamides with Amines." In Current Topics on Chemistry and Biochemistry Vol. 8, 123–33. B P International (a part of SCIENCEDOMAIN International), 2023. http://dx.doi.org/10.9734/bpi/ctcb/v8/4940e.

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2

Lambert, Tristan H. "Functional Group Interconversion." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0004.

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Chaozhong Li of the Shanghai Institute of Organic Chemistry reported (J. Am. Chem. Soc. 2012, 134, 10401) the silver nitrate catalyzed decarboxylative fluorination of carboxylic acids, which shows interesting chemoselectivity in substrates such as 1. A related decarboxylative chlorination was also reported by Li (J. Am. Chem. Soc. 2012, 134, 4258). Masahito Ochiai at the University of Tokushima has developed (Chem. Commun. 2012, 48, 982) an iodobenzene-catalyzed Hofmann rearrangement (e.g., 3 to 4) that proceeds via hypervalent iodine intermediates. The dehydrating agent T3P (propylphosphonic anhydride), an increasingly popular reagent for acylation chemistry, has been used (Tetrahedron Lett. 2012, 53, 1406) by Vommina Sureshbabu at Bangalore University to convert amino or peptide acids such as 5 to the corresponding thioacids with sodium sulfide. Jianqing Li and co-workers at Bristol-Myers Squibb have shown (Org. Lett. 2012, 14, 214) that trimethylaluminum, which has long been known to effect the direct amidation of esters, can also achieve the direct coupling of acids and amines, such as in the preparation of amide 8. The propensity of severely hindered 2,2,6,6-tetramethylpiperidine (TMP) amides such as 9 to undergo solvolysis at room temperature has been shown (Angew. Chem. Int. Ed. 2012, 51, 548) by Guy Lloyd-Jones and Kevin Booker-Milburn at the University of Bristol. The reaction proceeds by way of the ketene and is enabled by sterically induced destabilization of the usual conformation that allows conjugation of the nitrogen lone pair with the carbonyl. Matthias Beller at Universität Rostock has found (Angew. Chem. Int. Ed. 2012, 51, 3905) that primary amides may be transamidated via copper(II) catalysis. The conditions are mild enough that an epimerization-prone amide such as 11 undergoes no observable racemization during conversion to amide 13. A photochemical transamidation has been achieved (Chem. Sci. 2012, 3, 405) by Christian Bochet at the University of Fribourg that utilizes 385-nm light to activate a dinitroindoline amide in the presence of amines such as 15, which produces the amide 16. Notably, photochemical cleavage of the Ddz protecting group occurs at a shorter wavelength of 300 nm.

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