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Artykuły w czasopismach na temat „Late functionalization”

Autor: Grafiati

Data publikacji: 7 września 2024

Data aktualizacji: 31 lipca 2025

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1

Börgel, Jonas, and Tobias Ritter. "Late-Stage Functionalization." Chem 6, no. 8 (2020): 1877–87. http://dx.doi.org/10.1016/j.chempr.2020.07.007.

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McConnell, Cameron R., and Shih-Yuan Liu. "Late-stage functionalization of BN-heterocycles." Chemical Society Reviews 48, no. 13 (2019): 3436–53. http://dx.doi.org/10.1039/c9cs00218a.

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3

Bellina, Fabio. "Late-stage Functionalization of (hetero)arenes." Current Organic Chemistry 25, no. 18 (2021): 2045. http://dx.doi.org/10.2174/138527282518211007142734.

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4

Miller, Scott J., and Tobias Ritter. "Introduction: Remote and Late Stage Functionalization." Chemical Reviews 123, no. 24 (2023): 13867–68. http://dx.doi.org/10.1021/acs.chemrev.3c00800.

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5

Son, Jongwoo. "Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs." Beilstein Journal of Organic Chemistry 17 (July 26, 2021): 1733–51. http://dx.doi.org/10.3762/bjoc.17.122.

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The late-stage C–H functionalization of bioactive structural motifs is a powerful synthetic strategy for accessing advanced agrochemicals, bioimaging materials, and drug candidates, among other complex molecules. While traditional late-stage diversification relies on the use of precious transition metals, the utilization of 3d transition metals is an emerging approach in organic synthesis. Among the 3d metals, manganese catalysts have gained increasing attention for late-stage diversification due to the sustainability, cost-effectiveness, ease of operation, and reduced toxicity. Herein, we sum

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6

Kumar Hota, Sudhir, Dilsha Jinan, Satya Prakash Panda, Rittwika Pan, Basudev Sahoo, and Sandip Murarka. "Organophotoredox‐Catalyzed Late‐Stage Functionalization of Heterocycles." Asian Journal of Organic Chemistry 10, no. 8 (2021): 1848–60. http://dx.doi.org/10.1002/ajoc.202100234.

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7

Cernak, Tim, Kevin D. Dykstra, Sriram Tyagarajan, Petr Vachal, and Shane W. Krska. "The medicinal chemist's toolbox for late stage functionalization of drug-like molecules." Chemical Society Reviews 45, no. 3 (2016): 546–76. http://dx.doi.org/10.1039/c5cs00628g.

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The advent of modern C–H functionalization chemistries has enabled medicinal chemists to consider a synthetic strategy, late stage functionalization (LSF), which utilizes the C–H bonds of drug leads as points of diversification for generating new analogs.

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8

Greaney, Michael F., and David M. Whalley. "Recent Advances in the Smiles Rearrangement: New Opportunities for Arylation." Synthesis 54, no. 08 (2021): 1908–18. http://dx.doi.org/10.1055/a-1710-6289.

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AbstractThe Smiles rearrangement has undergone a renaissance in recent years providing new avenues for non-canonical arylation techniques in both the radical and polar regimes. This short review will discuss recent applications of the reaction (from 2017 to late 2021), including its relevance to areas such as heterocycle synthesis and the functionalization of alkenes and alkynes as well as glimpses at new directions for the field.1 Introduction2 Polar Smiles Rearrangements3 Radical Smiles: Alkene and Alkyne Functionalization4 Radical Smiles: Rearrangements via C–X Bond Cleavage5 Radical Smiles

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9

Barham, Joshua P., та Jaspreet Kaur. "Site-Selective C(sp3)–H Functionalizations Mediated by Hydrogen Atom Transfer Reactions via α-Amino/α-Amido Radicals". Synthesis 54, № 06 (2021): 1461–77. http://dx.doi.org/10.1055/a-1677-6619.

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AbstractAmines and amides, as N-containing compounds, are ubiquitous in pharmaceutically-active scaffolds, natural products, agrochemicals, and peptides. Amides in nature bear a key responsibility for imparting three-dimensional structure, such as in proteins. Structural modifications to amines and amides, especially at their positions α to N, bring about profound changes in biological activity oftentimes leading to more desirable pharmacological profiles of small drug molecules. A number of recent developments in synthetic methodology for the functionalizations of amines and amides omit the n

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10

Čorić, Ilija, and Jyoti Dhankhar. "Introduction to Spatial Anion Control for Direct C–H Arylation." Synlett 33, no. 06 (2022): 503–12. http://dx.doi.org/10.1055/s-0040-1719860.

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AbstractC–H activation of functionally rich molecules without the need for directing groups promises shorter organic syntheses and late-stage diversification of molecules for drug discovery. We highlight recent examples of palladium-catalyzed nondirected functionalization of C–H bonds in arenes as limiting substrates with a focus on the development of the concept of spatial anion control for direct C–H arylation.1 C–H Activation and the CMD Mechanism2 Nondirected C–H Functionalizations of Arenes as Limiting Substrates3 Nondirected C–H Arylation4 Spatial Anion Control for Direct C–H Arylation5

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11

Liu, Zilei, Jie Li, Suhua Li, Gencheng Li, K. Barry Sharpless, and Peng Wu. "SuFEx Click Chemistry Enabled Late-Stage Drug Functionalization." Journal of the American Chemical Society 140, no. 8 (2018): 2919–25. http://dx.doi.org/10.1021/jacs.7b12788.

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12

White, M. Christina, and Jinpeng Zhao. "Aliphatic C–H Oxidations for Late-Stage Functionalization." Journal of the American Chemical Society 140, no. 43 (2018): 13988–4009. http://dx.doi.org/10.1021/jacs.8b05195.

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13

Noisier, Anaïs F. M., Magnus J. Johansson, Laurent Knerr, et al. "Late‐Stage Functionalization of Histidine in Unprotected Peptides." Angewandte Chemie International Edition 58, no. 52 (2019): 19096–102. http://dx.doi.org/10.1002/anie.201910888.

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14

Noisier, Anaïs F. M., Magnus J. Johansson, Laurent Knerr, et al. "Late‐Stage Functionalization of Histidine in Unprotected Peptides." Angewandte Chemie 131, no. 52 (2019): 19272–78. http://dx.doi.org/10.1002/ange.201910888.

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15

Budhwan, Rajnish, Suman Yadav, and Sandip Murarka. "Late stage functionalization of heterocycles using hypervalent iodine(iii) reagents." Organic & Biomolecular Chemistry 17, no. 26 (2019): 6326–41. http://dx.doi.org/10.1039/c9ob00694j.

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16

Greunke, Christian, Janine Antosch, and Tobias A. M. Gulder. "Promiscuous hydroxylases for the functionalization of polycyclic tetramate macrolactams – conversion of ikarugamycin to butremycin." Chemical Communications 51, no. 25 (2015): 5334–36. http://dx.doi.org/10.1039/c5cc00843c.

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17

Zheng, Shasha, Gu Lingyue, Michelle Jui Hsien Ong, et al. "Divergent synthesis of 5′,7′-difluorinated dihydroxanthene-hemicyanine fused near-infrared fluorophores." Organic & Biomolecular Chemistry 17, no. 17 (2019): 4291–300. http://dx.doi.org/10.1039/c9ob00568d.

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18

Zhang, Sikun, Xiaodong Yang, Xu Liu та ін. "Dithienoazaborine derivatives with selective π-conjugated extension via late-stage functionalization". Journal of Materials Chemistry C 9, № 11 (2021): 4053–61. http://dx.doi.org/10.1039/d0tc05640e.

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19

Capaldo, Luca, Lorenzo Lafayette Quadri, and Davide Ravelli. "Photocatalytic hydrogen atom transfer: the philosopher's stone for late-stage functionalization?" Green Chemistry 22, no. 11 (2020): 3376–96. http://dx.doi.org/10.1039/d0gc01035a.

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20

Zhan, Bei-Bei, Meng-Xue Jiang, and Bing-Feng Shi. "Late-stage functionalization of peptides via a palladium-catalyzed C(sp3)–H activation strategy." Chemical Communications 56, no. 90 (2020): 13950–58. http://dx.doi.org/10.1039/d0cc06133f.

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21

Guo, Shuo, Deyaa I. AbuSalim, and Silas P. Cook. "Aqueous Benzylic C–H Trifluoromethylation for Late-Stage Functionalization." Journal of the American Chemical Society 140, no. 39 (2018): 12378–82. http://dx.doi.org/10.1021/jacs.8b08547.

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22

Shang, Ming, Ming-Ming Wang, Tyler G. Saint-Denis, Ming-Hong Li, Hui-Xiong Dai, and Jin-Quan Yu. "Copper-Mediated Late-Stage Functionalization of Heterocycle-Containing Molecules." Angewandte Chemie International Edition 56, no. 19 (2017): 5317–21. http://dx.doi.org/10.1002/anie.201611287.

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23

Shang, Ming, Ming-Ming Wang, Tyler G. Saint-Denis, Ming-Hong Li, Hui-Xiong Dai, and Jin-Quan Yu. "Copper-Mediated Late-Stage Functionalization of Heterocycle-Containing Molecules." Angewandte Chemie 129, no. 19 (2017): 5401–5. http://dx.doi.org/10.1002/ange.201611287.

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24

Konrad, David B., James A. Frank, and Dirk Trauner. "Synthesis of Redshifted Azobenzene Photoswitches by Late-Stage Functionalization." Chemistry - A European Journal 22, no. 13 (2016): 4364–68. http://dx.doi.org/10.1002/chem.201505061.

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25

Kuttruff, Christian A., Margit Haile, Johannes Kraml, and Christofer S. Tautermann. "Late-Stage Functionalization of Drug-Like Molecules Using Diversinates." ChemMedChem 13, no. 10 (2018): 983–87. http://dx.doi.org/10.1002/cmdc.201800151.

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26

Lv, Shuaipeng, Haitao Liu, Jie Kang, et al. "Palladium-catalyzed enol/enolate directed oxidative annulation: functionalized naphthofuroquinone synthesis and bioactivity evaluation." Chemical Communications 55, no. 98 (2019): 14729–32. http://dx.doi.org/10.1039/c9cc05233j.

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Diverse naphthoquinone-containing heterocycle synthesis has been developed via enol/enolate-directed palladium catalytic processes together with late-stage functionalization and lead compound development.

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27

Chen, Geshuyi, Zhe Chang, Pei Yuan, et al. "Late-stage functionalization of 5-nitrofurans derivatives and their antibacterial activities." RSC Advances 13, no. 5 (2023): 3204–9. http://dx.doi.org/10.1039/d2ra07676d.

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28

Cernak, Tim, Kevin D. Dykstra, Sriram Tyagarajan, Petr Vachal, and Shane W. Krska. "Correction: The medicinal chemist's toolbox for late stage functionalization of drug-like molecules." Chemical Society Reviews 46, no. 6 (2017): 1760. http://dx.doi.org/10.1039/c7cs90023f.

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29

da Silva, Thiago Sabino, Matheus da Silva Souza, Adriano Defini Andricopulo, and Fernando Coelho. "Discovery of indolizine lactones as anticancer agents and their optimization through late-stage functionalization." RSC Advances 13, no. 29 (2023): 20264–70. http://dx.doi.org/10.1039/d3ra03395c.

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30

Arisawa, Mitsuhiro, Shohei Ohno, Makoto Miyoshi та Kenichi Murai. "Non-Directed β- or γ-C(sp3)–H Functionalization of Saturated Nitrogen-Containing Heterocycles". Synthesis 53, № 17 (2021): 2947–60. http://dx.doi.org/10.1055/a-1483-4575.

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AbstractReactions that take place via C–H functionalization are valuable tools in organic synthesis because they can be used for the synthesis of target compounds and for the late-stage functionalization of bioactive compounds. Among these, non-directed C(sp3)–H functionalization reactions of saturated nitrogen-containing heterocycles have been developed in recent years. However, most of these lead to functionalization at the α-position relative to the heteroatom, and reactions at the β- or γ-positions are limited since these bonds are stronger and less electron-rich. Hence, in this review, we

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31

Adarsh Krishna, T. P., Baldev Edachery, and Sunil Athalathil. "Bakuchiol – a natural meroterpenoid: structure, isolation, synthesis and functionalization approaches." RSC Advances 12, no. 14 (2022): 8815–32. http://dx.doi.org/10.1039/d1ra08771a.

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The isolation methods, various chemical routes and late-stage functionalization approaches and structure–activity relationships of bakuchiol – a meroterpene class of natural product has been discussed in detail.

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32

van der Heide, Perry, Michele Retini, Fabiola Fanini, et al. "Giese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation." Beilstein Journal of Organic Chemistry 20 (December 17, 2024): 3274–80. https://doi.org/10.3762/bjoc.20.271.

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The rising popularity of bioconjugate therapeutics has led to growing interest in late-stage functionalization (LSF) of peptide scaffolds. α,β-Unsaturated amino acids like dehydroalanine (Dha) derivatives have emerged as particularly useful structures, as the electron-deficient olefin moiety can engage in late-stage functionalization reactions, like a Giese-type reaction. Cheap and widely available building blocks like organohalides can be converted into alkyl radicals by means of photoinduced silane-mediated halogen-atom transfer (XAT) to offer a mild and straightforward methodology of alkyla

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33

Li, Wei, Zhoulong Fan, Kaijun Geng, Youjun Xu, and Ao Zhang. "Late-stage diversification of biologically active pyridazinones via a direct C–H functionalization strategy." Organic & Biomolecular Chemistry 13, no. 2 (2015): 539–48. http://dx.doi.org/10.1039/c4ob02061h.

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34

Tali, Javeed Ahmad, Gulshan Kumar, Davinder Singh, and Ravi Shankar. "Palladium(ii) catalyzed site-selective C–H olefination of imidazo[1,2-a]pyridines." Organic & Biomolecular Chemistry 19, no. 43 (2021): 9401–6. http://dx.doi.org/10.1039/d1ob01683k.

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35

Hjerrild, Per, Thomas Tørring, and Thomas B. Poulsen. "Dehydration reactions in polyfunctional natural products." Natural Product Reports 37, no. 8 (2020): 1043–64. http://dx.doi.org/10.1039/d0np00009d.

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Here, we review methods for chemical dehydration of alcohols to alkenes and discuss the potential of late-stage functionalization by direct, site- and chemo-selective dehydration of complex molecular substrates.

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36

Cao, Hui, Qiang Cheng, and Armido Studer. "Radical and ionic meta -C–H functionalization of pyridines, quinolines, and isoquinolines." Science 378, no. 6621 (2022): 779–85. http://dx.doi.org/10.1126/science.ade6029.

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Carbon-hydrogen (C−H) functionalization of pyridines is a powerful tool for the rapid construction and derivatization of many agrochemicals, pharmaceuticals, and materials. Because of the inherent electronic properties of pyridines, selective meta -C−H functionalization is challenging. Here, we present a protocol for highly regioselective meta -C−H trifluoromethylation, perfluoroalkylation, chlorination, bromination, iodination, nitration, sulfanylation, and selenylation of pyridines through a redox-neutral dearomatization-rearomatization process. The introduced dearomative activation mode pro

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37

Schafer, Laurel L., and Cameron H. M. Zheng. "Recent Advances in Saturated N-Heterocycle C–H Bond Functionalization for Alkylated N-Heterocycle Synthesis." Synthesis, August 1, 2024. http://dx.doi.org/10.1055/s-0043-1775377.

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AbstractThe prominence of saturated N-heterocycle motifs in pharmaceuticals is undeniable. Challenges associated with the alkylation of saturated N-heterocycle scaffolds to efficiently access new drug analogues are hampered by synthetically laborious routes. Stereocontrolled alkyl-substitutions onto saturated N-heterocycles are particularly difficult to access in high yields by traditional synthetic methods. Alternatively, C–H bond functionalization provides a new and powerful synthetic avenue by directly and selectively functionalizing/alkylating/ arylating the abundantly available C–H bonds

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38

King-Smith, Emma, Felix A. Faber, Usa Reilly, et al. "Predictive Minisci late stage functionalization with transfer learning." Nature Communications 15, no. 1 (2024). http://dx.doi.org/10.1038/s41467-023-42145-1.

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AbstractStructural diversification of lead molecules is a key component of drug discovery to explore chemical space. Late-stage functionalizations (LSFs) are versatile methodologies capable of installing functional handles on richly decorated intermediates to deliver numerous diverse products in a single reaction. Predicting the regioselectivity of LSF is still an open challenge in the field. Numerous efforts from chemoinformatics and machine learning (ML) groups have made strides in this area. However, it is arduous to isolate and characterize the multitude of LSF products generated, limiting

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39

Wang, Yulei, Suman Dana, Hao Long, et al. "Electrochemical Late-Stage Functionalization." Chemical Reviews, September 26, 2023. http://dx.doi.org/10.1021/acs.chemrev.3c00158.

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40

Yang, Zixian, Jin-Tao Yu, and Changduo Pan. "Recent advances in C–H functionalization of 2H-indazoles." Organic & Biomolecular Chemistry, 2022. http://dx.doi.org/10.1039/d2ob01463g.

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Advances in the late-stage functionalization of 2H-indazoles, including C3-functionalization, ortho C2′–H functionalization and remote C–H functionalization at the benzene ring of 2H-indazoles, are reviewed.

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41

Xu, Jiayi, Yahui Zhang, Qiling Cai, et al. "Green Late‐Stage Functionalization of Tryptamines." Chemistry – A European Journal, June 13, 2024. http://dx.doi.org/10.1002/chem.202401436.

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An efficient and rapid protocol for the oxidative halogenation of tryptamines with 10% aqueous NaClO has been developed. This reaction is featured by its operational simplicity, metal‐free conditions, no purification, and high yield. Notably, the resulting key intermediates are suitable for further functionalization with various nucleophiles, including amines, N‐aromatic heterocycles, indoles and phenols. The overall transformation exhibits broad functional‐group tolerance and is applicable to the late‐stage functionalization of complex biorelevant molecules.

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42

"Baran Diversinates for late stage functionalization." Chemical & Engineering News Archive 92, no. 46 (2014): 37. http://dx.doi.org/10.1021/cen-09246-ad23.

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43

Bellotti, Peter, Huan-Ming Huang, Teresa Faber, and Frank Glorius. "Photocatalytic Late-Stage C–H Functionalization." Chemical Reviews, January 24, 2023. http://dx.doi.org/10.1021/acs.chemrev.2c00478.

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44

Docherty, Jamie H., Mishra Deepak Hareram, Luke M. Nichols, Ignacio Pérez-Ortega, Iñigo J. Vitorica-Yrezabal, and Igor Larrosa. "Precision installation of silyl synthetic handles within arenes by regiocontrolled ruthenium C(sp2)–H functionalization." Nature Catalysis, April 2, 2025. https://doi.org/10.1038/s41929-025-01309-6.

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Abstract The site-selective functionalization of C(sp 2)–H bonds represents a powerful strategy for the synthesis of structurally diverse compounds with broad applicability. Here we report efficient regioselective catalytic methods for the formation of benzyltrimethylsilanes through ruthenium-catalysed C(sp 2)–H silylmethylation. The developed protocols enable selective functionalization at both ortho and meta positions within arenes bearing N-based directing groups. The resulting silylmethyl compounds can undergo diverse transformations, including nucleophilic aromatic substitution, carbonyl

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45

Li, Yangyan, Madiha Butt, Wenhu Bao, Ruoqian Xie, and Gang Chen. "Progress in the Functionalization of Purines and Purine Nucleosides by Minisci Reactions Over the Past 50 Years." ChemCatChem, November 28, 2024. http://dx.doi.org/10.1002/cctc.202401550.

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Over the past decade, significant progress has been witnessed in the functionalization of purines and purine nucleosides via Minisci reactions. This review primarily focuses on the latest advancements in applying Minisci reactions to purine bases, while also including some notable early examples, with an emphasis on the late‐stage functionalization of purine nucleosides. The Minisci reaction, a radical‐based method, enables direct C–H functionalization of purines, facilitating the incorporation of a wide range of functional groups under mild conditions. Key developments discussed in this revie

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46

Nippa, David F., Kenneth Atz, Remo Hohler, et al. "Enabling late-stage drug diversification by high-throughput experimentation with geometric deep learning." Nature Chemistry, November 23, 2023. http://dx.doi.org/10.1038/s41557-023-01360-5.

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AbstractLate-stage functionalization is an economical approach to optimize the properties of drug candidates. However, the chemical complexity of drug molecules often makes late-stage diversification challenging. To address this problem, a late-stage functionalization platform based on geometric deep learning and high-throughput reaction screening was developed. Considering borylation as a critical step in late-stage functionalization, the computational model predicted reaction yields for diverse reaction conditions with a mean absolute error margin of 4–5%, while the reactivity of novel react

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47

Rocha, Eduardo, Yasmin Salmazo, Marcio Hayashi, César Zaragoza, and Emilio Lucca. "FUNCIONALIZAÇÃO DE LIGAÇÕES C—H EM ESTÁGIO TARDIO EM SÍNTESE ORGÂNICA." Química Nova, 2023. http://dx.doi.org/10.21577/0100-4042.20170949.

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LATE-STAGE FUNCTIONALIZATION OF C—H BONDS IN ORGANIC SYNTHESIS. The development of new strategies for the functionalization of the historically inert C—H bond arises as an excellent way to create new carbon—carbon and carbon— heteroatom bonds. With increasingly chemo- and site-selective methods that enables the late-stage functionalization of C—H bonds, the modification of specific sites in natural products and pharmaceuticals without altering their scaffold emerges as a powerful means for the diversification of complex molecules. In this review, we will introduce concepts of late-stage modifi

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48

Ritter, Tobias, and Florian Berger. "Site-Selective Late-Stage C–H Functionalization via Thianthrenium Salts." Synlett, April 13, 2021. http://dx.doi.org/10.1055/s-0040-1706034.

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AbstractThe high abundance of C–H bonds in organic molecules makes C–H functionalization a powerful approach to quickly increase the complexity of an organic molecule. However, the high abundance of C–H bonds also provides a challenge to C–H functionalization reactions: selectivity. While most C–H functionalization reactions produce mixtures of different products for most substrates, we have developed a highly selective method for aromatic C–H functionalization via sulfonium salts. The reaction does not require a certain directing group to be selective. The introduced functional group is a sul

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49

Barahdia, Aman, Karuna Thakare, Lipat Kaur, and Rahul Jain. "Endogenous group‐directed late‐stage C‐H functionalization of peptides." Advanced Synthesis & Catalysis, May 17, 2024. http://dx.doi.org/10.1002/adsc.202400373.

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Peptides are diverse in terms of their functional groups and side‐chain functionalities, and late‐stage C‐H functionalization plays a crucial role in their design. Approaches for such synthesis require pre‐installation and post‐removal of the directing group (DG). In recent times, chemical methods have been developed, focusing on the external DG‐free C‐H functionalization of peptides. These approaches utilize the inherent native functionality of peptides as DG to simplify synthetic routes, reducing synthetic steps, waste generation, enhancing sustainability, cost‐effectiveness, and operational

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"Manganese-Catalyzed Late-Stage Functionalization of Peptides." Synfacts 17, no. 06 (2021): 0707. http://dx.doi.org/10.1055/s-0040-1706212.

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