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Journal articles on the topic 'Direct C-H Functionalization'

Author: Grafiati
Published: 4 June 2021
Last updated: 7 September 2024

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1

Ye, Zhishi, Kristen E. Gettys, and Mingji Dai. "Opportunities and challenges for direct C–H functionalization of piperazines." Beilstein Journal of Organic Chemistry 12 (April 13, 2016): 702–15. http://dx.doi.org/10.3762/bjoc.12.70.

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Piperazine ranks within the top three most utilized N-heterocyclic moieties in FDA-approved small-molecule pharmaceuticals. Herein we summarize the current synthetic methods available to perform C–H functionalization on piperazines in order to lend structural diversity to this privileged drug scaffold. Multiple approaches such as those involving α-lithiation trapping, transition-metal-catalyzed α-C–H functionalizations, and photoredox catalysis are discussed. We also highlight the difficulties experienced when successful methods for α-C–H functionalization of acyclic amines and saturated mono-nitrogen heterocyclic compounds (such as piperidines and pyrrolidines) were applied to piperazine substrates.
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2

Čorić, Ilija, and Jyoti Dhankhar. "Introduction to Spatial Anion Control for Direct C–H Arylation." Synlett 33, no. 06 (February 1, 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 Coordination Chemistry with Spatial Anion Control6 Conclusion
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3

Verbitskiy, Egor, Gennady Rusinov, Oleg Chupakhin, and Valery Charushin. "Recent Advances in Direct C–H Functionalization of Pyrimidines." Synthesis 50, no. 02 (December 14, 2017): 193–210. http://dx.doi.org/10.1055/s-0036-1589520.

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Data spanning the period 2000–2017 on the direct C–H functionalization of pyrimidines are collected and discussed in this review. This demonstrates the surge of interest and creativity that this field of chemistry has experienced during the last two decades. Plausible applications of highly functionalized pyrimidines are also discussed.1 Introduction2 Transition-Metal-Catalyzed C–H Functionalization of Pyrimidine Derivatives3 Transition-Metal-Free Direct C–H Functionalization of Pyrimidine Derivatives4 Deprotonative Metalation of Pyrimidine Derivatives5 Conclusions
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4

Qiu, Guanyinsheng, and Jie Wu. "Transition metal-catalyzed direct remote C–H functionalization of alkyl groups via C(sp3)–H bond activation." Organic Chemistry Frontiers 2, no. 2 (2015): 169–78. http://dx.doi.org/10.1039/c4qo00207e.

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This review is focused on the recent advances in the transition metal-catalyzed direct remote C–H-functionalization of alkyl groups via C(sp3)–H bond activation. In general, carboxamide/ester-chelated β-functionalization reactions are summarized.
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5

Dhankhar, Jyoti, and Ilija Čorić. "Direct C–H Arylation." CHIMIA 76, no. 9 (September 21, 2022): 777. http://dx.doi.org/10.2533/chimia.2022.777.

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Bonds between hydrogen and carbon atoms are the most frequent type of bonds in organic molecules. The ability to replace hydrogen atoms by making other types of bonds to carbon atoms can enable simpler access to complex organic molecules by substituting multistep synthetic sequences. The use of transition metal catalysts to activate C–H bonds is particularly attractive as it offers control over the reactivity and selectivity through catalyst design. However, such functionalization includes the difficult breaking of strong C–H bonds that are not activated by the presence of other groups. Additionally, the common presence of a number of C–H bonds in a molecule raises the issue of site-selectivity because differentiation of C–H bonds that are in sterically and electronically similar environments is a challenge. We discuss selected recent developments that are a part of the long-term research interest in mild and selective C–H activation reactions with a focus on the replacement of C–H bonds with C–aryl groups and an emphasis on the work of our group.
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6

Siddiqui, Rafia, and Rashid Ali. "Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations." Beilstein Journal of Organic Chemistry 16 (February 26, 2020): 248–80. http://dx.doi.org/10.3762/bjoc.16.26.

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In recent years, the research area of direct C–H bond functionalizations was growing exponentially not only due to the ubiquity of inert C–H bonds in diverse organic compounds, including bioactive natural and nonnatural products, but also due to its impact on the discovery of pharmaceutical candidates and the total synthesis of intricate natural products. On the other hand, more recently, the field of photoredox catalysis has become an indispensable and unparalleled research topic in modern synthetic organic chemistry for the constructions of challenging bonds, having the foremost scope in academia, pharmacy, and industry. Therefore, the development of green, simpler, and effective methodologies to accomplish direct C–H bond functionalization is well overdue and highly desirable to the scientific community. In this review, we mainly highlight the impact on, and the utility of, photoredox catalysts in inert ortho and para C–H bond functionalizations. Although a surge of research papers, including reviews, demonstrating C–H functionalizations have been published in this vital area of research, to our best knowledge, this is the first review that focuses on ortho and para C–H functionalizations by photoredox catalysis to provide atom- and step-economic organic transformations. We are certain that this review will act as a promoter to highlight the application of photoredox catalysts for the functionalization of inert bonds in the domain of synthetic organic chemistry.
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7

Liu, Ying, Abdol Ghaffar Ebadi, Leila Youseftabar-Miri, Akbar Hassanpour, and Esmail Vessally. "Methods for direct C(sp2)–H bonds azidation." RSC Advances 9, no. 43 (2019): 25199–215. http://dx.doi.org/10.1039/c9ra04534a.

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8

Topczewski, Joseph J., and Melanie S. Sanford. "Carbon–hydrogen (C–H) bond activation at PdIV: a Frontier in C–H functionalization catalysis." Chemical Science 6, no. 1 (2015): 70–76. http://dx.doi.org/10.1039/c4sc02591a.

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9

Walker, Sarah E., James A. Jordan-Hore, David G. Johnson, Stuart A. Macgregor, and Ai-Lan Lee. "Palladium-Catalyzed Direct CH Functionalization of Benzoquinone." Angewandte Chemie International Edition 53, no. 50 (October 10, 2014): 13876–79. http://dx.doi.org/10.1002/anie.201408054.

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10

Walker, Sarah E., James A. Jordan-Hore, David G. Johnson, Stuart A. Macgregor, and Ai-Lan Lee. "Palladium-Catalyzed Direct CH Functionalization of Benzoquinone." Angewandte Chemie 126, no. 50 (October 10, 2014): 14096–99. http://dx.doi.org/10.1002/ange.201408054.

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11

Xu, Da-Zhen, Ren-Ming Hu, and Yi-Huan Lai. "Iron-Catalyzed Aerobic Oxidative Cross-Dehydrogenative C(sp3)–H/X–H (X = C, N, S) Coupling Reactions." Synlett 31, no. 18 (July 21, 2020): 1753–59. http://dx.doi.org/10.1055/s-0040-1707195.

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The direct functionalization of C(sp3)–H bonds is an attractive research topic in organic synthetic chemistry. The cross-dehydrogenative coupling (CDC) reaction provides a simple and powerful tool for the construction of C–C and C–heteroatom bonds. Recently, some progress has been made in the iron-catalyzed aerobic oxidative CDC reactions. Here, we present recent developments in the direct functionalization of C(sp3)–H bonds catalyzed by simple iron salts with molecular oxygen as the terminal oxidant.1 Introduction2 C(sp3)–C Bond Formation3 C(sp3)–N Bond Formation4 C(sp3)–S(Se) Bond Formation5 Conclusion and Outlook
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12

Uttry, Alexander, and Manuel van Gemmeren. "Direct C(sp3)–H Activation of Carboxylic Acids." Synthesis 52, no. 04 (October 17, 2019): 479–88. http://dx.doi.org/10.1055/s-0039-1690720.

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Carboxylic acids are important in a variety of research fields and applications. As a result, substantial efforts have been directed towards the C–H functionalization of such compounds. While the use of the carboxylic acid moiety as a native directing group for C(sp2)–H functionalization reactions is well established, as yet there is no general solution for the C(sp3)–H activation of aliphatic carboxylic acids and most endeavors have instead relied on the introduction of stronger directing groups. Recently however, novel ligands, tools, and strategies have emerged, which enable the use of free aliphatic carboxylic acids in C–H-activation-based transformations.1 Introduction2 Challenges in the C(sp3)–H Bond Activation of Carboxylic Acids3 The Lactonization of Aliphatic Carboxylic Acids4 The Directing Group Approach5 The Direct C–H Arylation of Aliphatic Carboxylic Acids6 The Direct C–H Olefination of Aliphatic Carboxylic Acids7 The Direct C–H Acetoxylation of Aliphatic Carboxylic Acids8 Summary
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13

Savchuk, M. I., E. S. Starnovskaya, Y. K. Shtaitz, A. P. Krinochkin, D. S. Kopchuk, S. Santra, M. Rahman, G. V. Zyryanov, V. L. Rusinov, and O. N. Chupakhin. "Direct synthesis of 5-arylethynyl-1,2,4-triazines via direct CH-functionalization." Chimica Techno Acta 7, no. 3 (September 1, 2020): 104–8. http://dx.doi.org/10.15826/chimtech.2020.7.3.02.

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14

Wang, Huamin, Kailun Liang, Wenpeng Xiong, Supravat Samanta, Wuqin Li, and Aiwen Lei. "Electrochemical oxidation-induced etherification via C(sp3)─H/O─H cross-coupling." Science Advances 6, no. 20 (May 2020): eaaz0590. http://dx.doi.org/10.1126/sciadv.aaz0590.

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Direct electrochemical construction of C─O bonds through C(sp3)─H functionalization still remains fundamentally challenging. Here, electrochemical oxidation-induced benzylic and allylic C(sp3)─H etherification has been developed. This protocol not only offers a practical strategy for the construction of C─O bonds using nonsolvent amounts of alcohols but also allows direct electrochemical benzylic and allylic C(sp3)─H functionalization in the absence of transition metal catalysis. A series of alcohols and benzylic and allylic C(sp3)─H compounds were compatible with this transformation. Mechanistically, the generation of aryl radical cation intermediates is the key to this C(sp3)─H etherification, as evidenced by radical probe substrate (cyclopropane ring opening) and electron paramagnetic resonance experiments.
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15

Murarka, Sandip, and Andrey Antonchick. "Metal-Catalyzed Oxidative Coupling of Ketones and Ketone Enolates." Synthesis 50, no. 11 (May 3, 2018): 2150–62. http://dx.doi.org/10.1055/s-0037-1609715.

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Recent years have witnessed a significant advancement in the field of radical oxidative coupling of ketones towards the synthesis of highly useful synthetic building blocks, such as 1,4-dicarbonyl compounds, and biologically important heterocyclic and carbocyclic compounds. Besides oxidative homo- and cross-coupling of enolates, other powerful methods involving direct C(sp3)–H functionalizations of ketones­ have emerged towards the synthesis of 1,4-dicarbonyl compounds. Moreover, direct α-C–H functionalization of ketones has also allowed an efficient access to carbocycles and heterocycles. This review summarizes all these developments made since 2008 in the field of metal-catalyzed/promoted radical-mediated functionalization of ketones at the α-position.1 Introduction2 Synthesis of 1,4-Dicarbonyl Compounds3 Synthesis of Heterocyclic Scaffolds4 Synthesis of Carbocyclic Scaffolds5 Conclusion
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16

Kamitani, Masahiro. "Direct C-H Functionalization of Methane by Homogeneous Catalysis." Journal of Synthetic Organic Chemistry, Japan 75, no. 12 (2017): 1290–91. http://dx.doi.org/10.5059/yukigoseikyokaishi.75.1290.

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17

Empel, Claire, Sripati Jana, and Rene M. Koenigs. "C-H Functionalization via Iron-Catalyzed Carbene-Transfer Reactions." Molecules 25, no. 4 (February 17, 2020): 880. http://dx.doi.org/10.3390/molecules25040880.

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The direct C-H functionalization reaction is one of the most efficient strategies by which to introduce new functional groups into small organic molecules. Over time, iron complexes have emerged as versatile catalysts for carbine-transfer reactions with diazoalkanes under mild and sustainable reaction conditions. In this review, we discuss the advances that have been made using iron catalysts to perform C-H functionalization reactions with diazoalkanes. We give an overview of early examples employing stoichiometric iron carbene complexes and continue with recent advances in the C-H functionalization of C(sp2)-H and C(sp3)-H bonds, concluding with the latest developments in enzymatic C-H functionalization reactions using iron-heme-containing enzymes.
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18

Warneke, Jonas, Martin Mayer, Markus Rohdenburg, Xin Ma, Judy K. Y. Liu, Max Grellmann, Sreekanta Debnath, et al. "Direct functionalization of C−H bonds by electrophilic anions." Proceedings of the National Academy of Sciences 117, no. 38 (September 2, 2020): 23374–79. http://dx.doi.org/10.1073/pnas.2004432117.

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Alkanes and [B12X12]2−(X = Cl, Br) are both stable compounds which are difficult to functionalize. Here we demonstrate the formation of a boron−carbon bond between these substances in a two-step process. Fragmentation of [B12X12]2−in the gas phase generates highly reactive [B12X11]−ions which spontaneously react with alkanes. The reaction mechanism was investigated using tandem mass spectrometry and gas-phase vibrational spectroscopy combined with electronic structure calculations. [B12X11]−reacts by an electrophilic substitution of a proton in an alkane resulting in a B−C bond formation. The product is a dianionic [B12X11CnH2n+1]2−species, to which H+is electrostatically bound. High-flux ion soft landing was performed to codeposit [B12X11]−and complex organic molecules (phthalates) in thin layers on surfaces. Molecular structure analysis of the product films revealed that C−H functionalization by [B12X11]−occurred in the presence of other more reactive functional groups. This observation demonstrates the utility of highly reactive fragment ions for selective bond formation processes and may pave the way for the use of gas-phase ion chemistry for the generation of complex molecular structures in the condensed phase.
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19

Verbitskiy, Egor, Gennady Rusinov, Oleg Chupakhin, and Valery Charushin. "Recent Advances in Direct C–H Functionalization of Pyrimidines." Synthesis 50, no. 02 (January 2018): e1-e1. http://dx.doi.org/10.1055/s-0036-1589526.

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20

Rueping, Magnus, and Nikita Tolstoluzhsky. "Copper Catalyzed C−H Functionalization for Direct Mannich Reactions." Organic Letters 13, no. 5 (March 4, 2011): 1095–97. http://dx.doi.org/10.1021/ol103150g.

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21

Liron, Frédéric, Julie Oble, Mélanie M. Lorion, and Giovanni Poli. "Direct Allylic Functionalization Through Pd-Catalyzed C-H Activation." European Journal of Organic Chemistry 2014, no. 27 (May 6, 2014): 5863–83. http://dx.doi.org/10.1002/ejoc.201402049.

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22

Tolnai, Gergely L., Anna Székely, Zita Makó, Tamás Gáti, János Daru, Tamás Bihari, András Stirling, and Zoltán Novák. "Efficient direct 2,2,2-trifluoroethylation of indoles via C–H functionalization." Chemical Communications 51, no. 21 (2015): 4488–91. http://dx.doi.org/10.1039/c5cc00519a.

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23

Zhang, Tong, Yue-Hua Wu, Nai-Xing Wang, and Yalan Xing. "Advances in C(sp3)–H Bond Functionalization via Radical Processes." Synthesis 51, no. 24 (September 13, 2019): 4531–48. http://dx.doi.org/10.1055/s-0039-1690674.

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C(sp3)–H Bonds are the most common structures in organic molecules. In recent years, the direct functionalization of C(sp3)–H bonds has attracted wide attention and made significant progress. This review mainly focuses on C(sp3)–H bond functionalization of alkanes with or without functional groups via radical processes reported since 2017. In particular, three methods of generating free radicals are discussed: the use of a radical initiator such as TBHP or DTBP; photocatalysis, and via 1,5-hydrogen atom transfer (1,5-HAT).1 Introduction2 C(sp3)–H Bond Functionalization of Alkanes3 C(sp3)–H Bond Functionalization of Alkanes with a Functional Group4 Conclusions
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24

Qiu, Guanyinsheng, and Jie Wu. "Correction: Transition metal-catalyzed direct remote C–H functionalization of alkyl groups via C(sp3)–H bond activation." Organic Chemistry Frontiers 2, no. 7 (2015): 859. http://dx.doi.org/10.1039/c5qo90023a.

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Correction for ‘Transition metal-catalyzed direct remote C–H functionalization of alkyl groups via C(sp3)–H bond activation’ by Guanyinsheng Qiu, et al., Org. Chem. Front., 2015, 2, 169–178.
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25

Bagdi, Avik Kumar, and Alakananda Hajra. "Visible light promoted C–H functionalization of imidazoheterocycles." Organic & Biomolecular Chemistry 18, no. 14 (2020): 2611–31. http://dx.doi.org/10.1039/d0ob00246a.

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26

Gu, Lijun, Ying Gao, Xianhong Ai, Cheng Jin, Yonghui He, Ganpeng Li, and Minglong Yuan. "Direct alkylheteroarylation of alkenes via photoredox mediated C–H functionalization." Chemical Communications 53, no. 96 (2017): 12946–49. http://dx.doi.org/10.1039/c7cc06484e.

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The direct alkylheteroarylation of alkenes with cyclic and acyclic ethers via distal heteroaryl ipso-migration has been accomplished through the design of a photoredox-mediated C–H functionalization pathway.
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27

Payra, Soumen, Arijit Saha, Sandip Guchhait, and Subhash Banerjee. "Direct CuO nanoparticle-catalyzed synthesis of poly-substituted furans via oxidative C–H/C–H functionalization in aqueous medium." RSC Advances 6, no. 40 (2016): 33462–67. http://dx.doi.org/10.1039/c6ra04181g.

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Here, we have reported CuO nanoparticles catalyzed synthesis of poly-functionalized furan derivatives via direct functionalization of α,β-unsaturated carbonyl compounds through conjugate addition initiated domino reactions in aqueous ethanol.
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28

Gao, Pin, Yu-Rui Gu, and Xin-Hua Duan. "Direct C–H Functionalization of Heteroarenes via Redox-Neutral Radical Process: A Facile Route to C–C Bonds Formation." Synthesis 49, no. 15 (July 6, 2017): 3407–21. http://dx.doi.org/10.1055/s-0036-1588493.

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Aromatic heterocycles are an important class of compounds found in a wide range of natural products, pharmaceutically active molecules and organic materials. Recently, the direct radical functionalization of heteroaromatic C–H bonds has become an efficient and attractive method to access substituted heteroarenes. Especially, redox-neutral radical reactions have attracted much attention of chemists due to their potential advantages such as mild conditions, free of external oxidants, and good functional group tolerance. So far, a series of redox-neutral radical reactions have been developed. In this review, we mainly focus on the recent advance in direct redox-neutral radical C–H functionalization of heteroarenes. Herein, the direct C–H arylation, C–H alkylation, and C–H fluoroalkylation of heteroarenes are represented respectively, providing practical routes to C–C bond formation.1 Introduction2 C–H Arylation of Heteroarenes with Aryl Radicals3 C–H Alkylation of Heteroarenes with Alkyl Radicals4 C–H Fluoroalkylation of Heteroarenes with Fluorine-Containing Carbon Radicals5 Concluding Remarks
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29

Sun, Jinwei, Fuyao Wang, Yongmiao Shen, Huizhen Zhi, Hui Wu, and Yun Liu. "Palladium-catalyzed direct and regioselective C–H acyloxylation of indolizines." Organic & Biomolecular Chemistry 13, no. 40 (2015): 10236–43. http://dx.doi.org/10.1039/c5ob01359c.

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A direct and highly regioselective C1-acyloxylation of indolizines was developed via palladium-catalyzed C–H functionalization. In this reaction, the regioselectivity was achieved in the absence of a directing group.
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30

McNally, Andrew, Ryan Dolewski, and Michael Hilton. "4-Selective Pyridine Functionalization Reactions via Heterocyclic Phosphonium Salts." Synlett 29, no. 01 (December 12, 2017): 08–14. http://dx.doi.org/10.1055/s-0036-1591850.

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Pyridines are widely used across the chemical sciences in applications ranging from pharmaceuticals, ligands for metal complex and battery technologies. Direct functionalization of pyridine C–H bonds is an important strategy to make useful pyridine derivatives, but there are few ways to selectively transform the 4-position of the scaffold. We recently reported that pyridines can be converted into heterocyclic phosphonium salts that can serve as generic handles for multiple subsequent bond-forming processes. Reactions with nucleophiles and transition-metal cross-couplings will be described to make C–O, C–S, C–N, and C–C bonds in a diverse range of pyridines including those embedded in complex pharmaceuticals.1 Introduction2 Direct, Regioselective Functionalization of Pyridines3 4-Position Selectivity via Metal Catalysis4 Versatile Functional Groups versus Specific Bond Constructions5 Phosphonium Salts as Reagents for Pyridine Functionalization6 Conclusions
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31

Chen, Dengfeng, Qingyuan Feng, Yunqin Yang, Xu-Min Cai, Fei Wang, and Shenlin Huang. "Metal-free O–H/C–H difunctionalization of phenols by o-hydroxyarylsulfonium salts in water." Chemical Science 8, no. 2 (2017): 1601–6. http://dx.doi.org/10.1039/c6sc04504a.

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32

Tian, Yao, Xiubin Bu, Yuanrui Chen, Luohe Wang, Junnan E, Jing Zeng, Hao Xu, Aihong Han, Xiaobo Yang, and Zhen Zhao. "Visible-Light-Driven α-C(sp3)–H Bond Functionalization of Glycine Derivatives." Catalysts 13, no. 12 (December 8, 2023): 1502. http://dx.doi.org/10.3390/catal13121502.

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The glycine motif is widely prevalent in bioactive peptides. Thus, the direct and precise modification of glycine derivatives has attracted significant attention over the past few decades. Among various protocols for the modification of glycine derivatives, the visible-light-driven direct α-C(sp3)–H bond functionalization of glycine derivatives has emerged as a powerful tool to achieve this objective, owing to its merits in atom economy, selectivity, reaction simplicity, and sustainability. This review summarizes the recent advancements in visible-light-driven direct α-C(sp3)–H bond functionalization of glycine derivatives. The contents of this review are organized based on the photocatalysts employed and the various reaction modes in the functionalization process. The mechanism, the challenges encountered, and future trends are also discussed, enabling readers to understand the current developmental status in this field.
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33

Barboza, Amanda Aline, Juliana Arantes Dantas, Guilherme Augusto de Melo Jardim, Marco Antonio Barbosa Ferreira, Mateus Oliveira Costa, and Attilio Chiavegatti. "Recent Advances in Palladium-Catalyzed Oxidative Couplings in the Synthesis/Functionalization of Cyclic Scaffolds Using Molecular Oxygen as the Sole Oxidant." Synthesis 54, no. 09 (November 19, 2021): 2081–102. http://dx.doi.org/10.1055/a-1701-7397.

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AbstractOver the past years, Pd(II)-catalyzed oxidative couplings have enabled the construction of molecular scaffolds with high structural diversity via C–C, C–N and C–O bond-forming reactions. In contrast to the use of stoichiometric amounts of more common oxidants, such as metal salts (Cu and Ag) and benzoquinone derivatives, the use of molecular oxygen for the direct or indirect regeneration of Pd(II) species presents itself as a more viable alternative in terms of economy and sustainability. In this review, we describe recent advances on the development of Pd-catalyzed oxidative cyclizations/functionalizations, where molecular oxygen plays a pivotal role as the sole stoichiometric oxidant.1 Introduction2 Oxidative C–C and C–Nu Coupling2.1 Intramolecular Oxidative C–Nu Heterocyclization Reactions2.1.1 C–H Activation2.1.2 Wacker/Aza-Wacker-Type Cyclization2.1.3 Tandem Wacker/Aza-Wacker and Cyclization/Cross-Coupling Reactions2.2 Intermolecular Oxidative C–Nu Heterocoupling Reactions2.3 Intramolecular Oxidative (C–C) Carbocyclization Reactions2.4 Intermolecular Oxidative C–C Coupling Reactions2.4.1 Cyclization Reactions2.4.2 Cross-Coupling Reactions2.4.3 Homo-Coupling Reactions3 Aerobic Dehydrogenative Coupling/Functionalization4 Oxidative C–H Functionalization5 Summary
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34

Aziz, Jessy, and Sandrine Piguel. "An Update on Direct C–H Bond Functionalization of Nitrogen-Containing Fused Heterocycles." Synthesis 49, no. 20 (August 25, 2017): 4562–85. http://dx.doi.org/10.1055/s-0036-1590859.

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This report highlights the recent advances in direct C–H bond functionalization of 5,5- and 6,5-fused heterocycles containing at least two nitrogen atoms. Besides C–C bond formation, C–N, C–S, C–P, and C–Si bonds can also be created via a metal-catalyzed process. Some examples, where a C–H functionalization approach was applied for the synthesis of drug candidates, will be presented as well.1 Introduction2 C–H Functionalization Reactions of N-Containing Heterocycles2.1 Imidazo[1,2-a]pyridines2.2 Pyrrolo[1,2-a]pyrazines2.3 Imidazo[1,2-b]pyrazoles2.4 Imidazo[1,2-a]pyrimidines2.5 Imidazo[1,2-a]pyrazines and Imidazo[1,5-a]pyrazines2.6 Imidazo[1,2-b]pyridazines2.7 Imidazo[4,5-b]pyridines and Imidazo[4,5-c]pyridines2.8 Pyrazolo[3,4-b]pyridines2.9 Pyrazolo[1,5-a]pyrimidines2.10 Pyrrolo[2,3-d]pyrimidines and Pyrrolo[3,2-d]pyrimidines2.11 Imidazo[1,2-b][1,2,4]triazines2.12 Imidazo[1,2-b][1,2,4,5]tetrazines3 Outlook4 Conclusion
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35

Li, Mingzong, Liangxi Li, and Haibo Ge. "Direct C-3-Alkenylation of Quinolones via Palladium-Catalyzed CH Functionalization." Advanced Synthesis & Catalysis 352, no. 14-15 (September 24, 2010): 2445–49. http://dx.doi.org/10.1002/adsc.201000364.

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Nagasawa, Shota. "Direct Aromatic C-H Oxygenation Aspiring to Late-stage Functionalization." Journal of Synthetic Organic Chemistry, Japan 80, no. 4 (April 1, 2022): 377–78. http://dx.doi.org/10.5059/yukigoseikyokaishi.80.377.

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37

Garza-Sanchez, R. Aleyda, Adrian Tlahuext-Aca, Ghazal Tavakoli, and Frank Glorius. "Visible Light-Mediated Direct Decarboxylative C–H Functionalization of Heteroarenes." ACS Catalysis 7, no. 6 (May 16, 2017): 4057–61. http://dx.doi.org/10.1021/acscatal.7b01133.

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38

Rego Campello, Hugo, Silvia G. Del Villar, Aurélien Honraedt, Teresa Minguez, A. Sofia F. Oliveira, Kara E. Ranaghan, Deborah K. Shoemark, et al. "Unlocking Nicotinic Selectivity via Direct C‒H Functionalization of (−)-Cytisine." Chem 4, no. 7 (July 2018): 1710–25. http://dx.doi.org/10.1016/j.chempr.2018.05.007.

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39

Chen, Weijie, Longle Ma, Anirudra Paul, and Daniel Seidel. "Direct α-C–H bond functionalization of unprotected cyclic amines." Nature Chemistry 10, no. 2 (November 6, 2017): 165–69. http://dx.doi.org/10.1038/nchem.2871.

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40

Luzung, Michael R, Chad A Lewis, and Phil S Baran. "Direct, ChemoselectiveN-tert-Prenylation of Indoles by CH Functionalization." Angewandte Chemie International Edition 48, no. 38 (September 7, 2009): 7025–29. http://dx.doi.org/10.1002/anie.200902761.

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41

Luzung, Michael R, Chad A Lewis, and Phil S Baran. "Direct, ChemoselectiveN-tert-Prenylation of Indoles by CH Functionalization." Angewandte Chemie 121, no. 38 (September 7, 2009): 7159–63. http://dx.doi.org/10.1002/ange.200902761.

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42

Walker, Sarah E., James A. Jordan-Hore, David G. Johnson, Stuart A. Macgregor, and Ai-Lan Lee. "ChemInform Abstract: Palladium-Catalyzed Direct C-H Functionalization of Benzoquinone." ChemInform 46, no. 19 (April 23, 2015): no. http://dx.doi.org/10.1002/chin.201519117.

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43

Zhang, Fulin, Luoting Xin, Saihu Liao, Xueliang Huang, and Yinghua Yu. "Recent Advances in Palladium-Catalyzed Bridging C–H Activation by Using Alkenes, Alkynes or Diazo Compounds as Bridging Reagents." Synthesis 53, no. 02 (September 22, 2020): 238–54. http://dx.doi.org/10.1055/s-0040-1707268.

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AbstractTransition-metal-catalyzed direct inert C–H bond functionalization has attracted much attention over the past decades. However, because of the high strain energy of the suspected palladacycle generated via C–H bond palladation, direct functionalization of a C–H bond less than a three-bond distance from a catalyst center is highly challenging. In this short review, we summarize the advances on palladium-catalyzed bridging C–H activation, in which an inert proximal C–H bond palladation is promoted by the elementary step of migratory insertion of an alkene, an alkyne or a metal carbene intermediate.1 Introduction2 Palladium-Catalyzed Alkene Bridging C–H Activation2.1 Intramolecular Reactions2.2 Intermolecular Reactions3 Palladium-Catalyzed Alkyne Bridging C–H Activation3.1 Intermolecular Reactions3.2 Intramolecular Reactions4 Palladium-Catalyzed Carbene Bridging C–H Activation5 Conclusion and Outlook
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44

Valentini, Federica, Oriana Piermatti, and Luigi Vaccaro. "Metal and Metal Oxide Nanoparticles Catalyzed C–H Activation for C–O and C–X (X = Halogen, B, P, S, Se) Bond Formation." Catalysts 13, no. 1 (December 22, 2022): 16. http://dx.doi.org/10.3390/catal13010016.

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The direct functionalization of an inactivated C–H bond has become an attractive approach to evolve toward step-economy, atom-efficient and environmentally sustainable processes. In this regard, the design and preparation of highly active metal nanoparticles as efficient catalysts for C–H bond activation under mild reaction conditions still continue to be investigated. This review focuses on the functionalization of un-activated C(sp3)–H, C(sp2)–H and C(sp)–H bonds exploiting metal and metal oxide nanoparticles C–H activation for C–O and C–X (X = Halogen, B, P, S, Se) bond formation, resulting in more sustainable access to industrial production.
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45

van Gemmeren, Manuel, and Alexander Uttry. "The Direct Pd-Catalyzed β-C(sp3)–H Activation of Carboxylic Acids." Synlett 29, no. 15 (May 23, 2018): 1937–43. http://dx.doi.org/10.1055/s-0037-1610150.

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The carboxylic acid moiety is one of the most versatile and abundant functional groups. However, despite of tremendous progress in the field of C–H functionalization reactions its use as a directing group for C(sp3)–H activation has remained limited. In this Synpact article we present the challenges associated with the carboxylic acid moiety as a native directing group and report on the newest developments in this field, including our recent study in which we developed a generally applicable protocol for the direct palladium catalyzed β-C(sp3)–H arylation of propionic acid and related α-branched aliphatic acids giving access to hydrocinnamic acids derivatives in a highly straightforward manner.1 Introduction2 Challenges in the C(sp3)–H Bond Activation of Carboxylic Acids3 History/State of the Art4 Studies towards a General β-C(sp3)–H Functionalization of ­Aliphatic Acids5 Conclusion
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46

Cai, Xiao-Hua, Meng-Zhi Yang, and Bing Xie. "Recent Investigations on the Functionalizations of C(sp3)-H Bonds Adjacent to a Heteroatom." Letters in Organic Chemistry 16, no. 10 (August 23, 2019): 779–801. http://dx.doi.org/10.2174/1570178616666190123131353.

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The selective functionalization of unactivated C(sp3)-H bonds has been regarded as an efficient and atom-economical approach for the formation of carbon-carbon or carbon-heteroatom bonds in modern organic synthesis. Especially, the oxidative activation of C(sp3)–H bonds adjacent to a heteroatom exhibits quite significant features in synthetic chemistry. For example, the direct functionalizations of amines, amides and ethers present important alternative tactics for the synthesis of various novel and useful molecules from simple starting materials. Many remarkable achievements in the area had continuously been made in the past decades. Here we reviewed recent investigations on the transformations of C(sp3)-H bond adjacent to a heteroatom.
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47

Chen, Su, Prabhat Ranjan, Leonid G. Voskressensky, Erik V. Van der Eycken, and Upendra K. Sharma. "Recent Developments in Transition-Metal Catalyzed Direct C–H Alkenylation, Alkylation, and Alkynylation of Azoles." Molecules 25, no. 21 (October 27, 2020): 4970. http://dx.doi.org/10.3390/molecules25214970.

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The transition metal-catalyzed C–H bond functionalization of azoles has emerged as one of the most important strategies to decorate these biologically important scaffolds. Despite significant progress in the C–H functionalization of various heteroarenes, the regioselective alkylation and alkenylation of azoles are still arduous transformations in many cases. This review covers recent advances in the direct C–H alkenylation, alkylation and alkynylation of azoles utilizing transition metal-catalysis. Moreover, the limitations of different strategies, chemoselectivity and regioselectivity issues will be discussed in this review.
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48

Zhao, L., O. Basle, and C. J. Li. "Site-specific C-functionalization of free-(NH) peptides and glycine derivatives via direct C-H bond functionalization." Proceedings of the National Academy of Sciences 106, no. 11 (February 27, 2009): 4106–11. http://dx.doi.org/10.1073/pnas.0809052106.

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49

Yang, Youqing, and Zhuangzhi Shi. "Regioselective direct arylation of indoles on the benzenoid moiety." Chemical Communications 54, no. 14 (2018): 1676–85. http://dx.doi.org/10.1039/c7cc08752g.

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50

Zhu, Tonghao, Shimin Xie, Pornchai Rojsitthisak, and Jie Wu. "Recent advances in the direct β-C(sp2)–H functionalization of enamides." Organic & Biomolecular Chemistry 18, no. 8 (2020): 1504–21. http://dx.doi.org/10.1039/c9ob02649e.

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Recent advances in the direct β-C(sp2)–H functionalization of enamides, mainly including arylation, alkenylation, alkynylation, alkylation, acylation, sulfonylation, phosphorylation, and others, are reported.
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