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Journal articles on the topic 'C–H Bond - Maleimides'

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Author: Grafiati

Published: 6 September 2023

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1

He, Qiyuan, Yusuke Ano, and Naoto Chatani. "The Pd-catalyzed C–H alkylation of ortho-methyl-substituted aromatic amides with maleimide occurs preferentially at the ortho-methyl C–H bond over the ortho-C–H bond." Chemical Communications 55, no. 67 (2019): 9983–86. http://dx.doi.org/10.1039/c9cc05321b.

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2

Zhao, Sheng-Yin, Hong-Ru Tan, Lun Wang, Jia-Nan Zhu, and Zhen-Hua Yang. "Iodine-Promoted C(sp 2)–H Thiolation of Maleimides with Dimethyl Sulfoxide and Thiols." Synthesis 50, no. 20 (July 30, 2018): 4113–23. http://dx.doi.org/10.1055/s-0037-1609585.

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Iodine-promoted C(sp 2)–H methylthiolation of maleimides using DMSO as synthon has been developed to afford 3-methylthiomaleimides in moderate yields under metal-free conditions. In addition, 3-thiomaleimides were synthesized from maleimides and thiols in the presence of iodine and triethylamine. The methods are simple and efficient for the formation of C–S bond.

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3

Pan, Changduo, Yun Wang, Chao Wu, and Jin-Tao Yu. "Rhodium-catalyzed C7-alkylation of indolines with maleimides." Organic & Biomolecular Chemistry 16, no. 5 (2018): 693–97. http://dx.doi.org/10.1039/c7ob03039h.

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4

Jeganmohan, Masilamani, Meledath Sudhakaran Keerthana, and Ramasamy Manoharan. "Cobalt(III)-Catalyzed Redox-Neutral Coupling of Acrylamides with Activated Alkenes via C–H Bond Activation." Synthesis 52, no. 11 (March 30, 2020): 1625–33. http://dx.doi.org/10.1055/s-0039-1690866.

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A cobalt(III)-catalyzed coupling of substituted acrylamides with maleimides in the presence of 30 mol% pivalic acid providing olefin-migrated succinimide derivatives in a redox-neutral manner is described. The coupling reaction was examined with various substituted acrylamides and maleimides. The scope of the C–H alkylation reaction was also examined with substituted acrylates. A possible reaction mechanism involving a five-membered cobaltocycle as a key intermediate is proposed.

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5

Sun, Meng, Xiang-Xiang Chen, Jiang-Tao Ren, Jing-Lei Xu, Hu Xie, Wei Sun, and Ya-Min Li. "Cobalt(III)-Catalyzed 1,4-Addition of C(sp3)–H Bonds to Maleimides." Synlett 29, no. 12 (May 29, 2018): 1601–6. http://dx.doi.org/10.1055/s-0037-1609847.

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Quinolines and succinimides play a crucial role in many pharmaceutical and natural products. Although sp2 C–H bond addition reactions have been extensively investigated, Co(III)-catalyzed sp3 C–H bond 1,4-addition reactions are relatively unexplored. In this manuscript, an efficient and atom-economic protocol for alkylation reactions of 8-methylquinolines with maleimides is presented. The reaction exhibits exceptional reactivity, satisfactory yields, excellent chemo- and regioselectivity, and tolerates a variety of functional groups.

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6

Bettadapur, Kiran R., Veeranjaneyulu Lanke, and Kandikere Ramaiah Prabhu. "A deciduous directing group approach for the addition of aryl and vinyl nucleophiles to maleimides." Chemical Communications 53, no. 46 (2017): 6251–54. http://dx.doi.org/10.1039/c7cc02392h.

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A Rh(iii)-catalyzed C–H activation followed by conjugate addition to maleimides, using carboxylic acid as a traceless/deciduous directing group, to formally furnish a C_sp2–C_sp3 bond is presented.

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7

Zhao, Sheng-Yin, Zhen-Hua Yang, Jia-Nan Zhu, Ze-Hui Jin, and Jian Zheng. "Copper-Catalyzed Intermolecular Thioamination of Maleimides with Thiols and Formamides: A One-Step Construction of 3-Amino-4-thiomaleimides Using Formamides as Nitrogen Sources." Synthesis 50, no. 23 (August 7, 2018): 4627–36. http://dx.doi.org/10.1055/s-0037-1610536.

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A highly efficient copper-catalyzed intermolecular C(sp2)–H thioamination of maleimides with thiols and formamides in the presence of fluoroboric acid is reported using various readily available formamides as nitrogen sources and solvents. A diverse range of 3-amino-4-thiomaleimides is obtained with good yields under mild conditions, involving C–N and C–S bond formation. This methodology enriches current C–N and C–S bond formation chemistry and features operational simplicity and excellent functional-group tolerance.

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8

Chen, Xiangxiang, Jiangtao Ren, Hu Xie, Wei Sun, Meng Sun, and Biao Wu. "Cobalt(iii)-catalyzed 1,4-addition of C–H bonds of oximes to maleimides." Organic Chemistry Frontiers 5, no. 2 (2018): 184–88. http://dx.doi.org/10.1039/c7qo00687j.

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9

Mangialetto, Jessica, Kiano Gorissen, Lise Vermeersch, Bruno Van Mele, Niko Van den Brande, and Freija De Vleeschouwer. "Hydrogen-Bond-Assisted Diels–Alder Kinetics or Self-Healing in Reversible Polymer Networks? A Combined Experimental and Theoretical Study." Molecules 27, no. 6 (March 17, 2022): 1961. http://dx.doi.org/10.3390/molecules27061961.

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Diels–Alder (DA) cycloadditions in reversible polymer networks are important for designing sustainable materials with self-healing properties. In this study, the DA kinetics of hydroxyl-substituted bis- and tetrafunctional furans with bis- and tris-functional maleimides, both containing ether-functionalized spacers, is investigated by modelling two equilibria representing the endo and exo cycloadduct formation. Concretely, the potential catalysis of the DA reaction through hydrogen bonding between hydroxyl of the furans and carbonyl of the maleimides or ether of the spacers is experimentally and theoretically scrutinized. Initial reaction rates and forward DA rate constants are determined by microcalorimetry at 20 °C for a model series of reversible networks, extended with (i) a hydroxyl-free network and hydroxyl-free linear or branched systems, and (ii) polypropylene glycol additives, increasing the hydroxyl concentration. A computational density-functional theory study is carried out on the endo and exo cycloadditions of furan and maleimide derivatives, representative for the experimental ones, in the absence and presence of ethylene glycol as additive. Additionally, an ester-substituted furan was investigated as a hydroxyl-free system for comparison. Experiment and theory indicate that the catalytic effect of H-bonding is absent or very limited. While increased concentration of H-bonding could in theory catalyze the DA reaction, the experimental results rule out this supposition.

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10

Muniraj, Nachimuthu, and Kandikere Ramaiah Prabhu. "Cobalt(III)-Catalyzed C–H Activation: Azo Directed Selective 1,4-Addition of Ortho C–H Bond to Maleimides." Journal of Organic Chemistry 82, no. 13 (June 19, 2017): 6913–21. http://dx.doi.org/10.1021/acs.joc.7b01094.

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11

Keshri, Puspam, Kiran R. Bettadapur, Veeranjaneyulu Lanke, and Kandikere Ramaiah Prabhu. "Ru(II)-Catalyzed C–H Activation: Amide-Directed 1,4-Addition of the Ortho C–H Bond to Maleimides." Journal of Organic Chemistry 81, no. 14 (July 7, 2016): 6056–65. http://dx.doi.org/10.1021/acs.joc.6b01160.

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12

Bettadapur, Kiran R., Veeranjaneyulu Lanke, and Kandikere Ramaiah Prabhu. "Ru (II)-Catalyzed C–H Activation: Ketone-Directed Novel 1,4-Addition of Ortho C–H Bond to Maleimides." Organic Letters 17, no. 19 (September 8, 2015): 4658–61. http://dx.doi.org/10.1021/acs.orglett.5b01810.

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13

Li, Hongji, Wenjie Zhang, Xueyan Liu, and Zhenfeng Tian. "Rh(III)-Catalyzed Olefination and Alkylation of Arenes with Maleimides: A Tunable Strategy for C(sp2)–H Functionalization." Synthesis 53, no. 13 (February 15, 2021): 2229–39. http://dx.doi.org/10.1055/s-0037-1610765.

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AbstractWe herein report a new nitrogen-directed Rh(III)-catalyzed C(sp2)–H bond functionalization of N-nitrosoanilines and azoxybenzenes with maleimides as a coupling partner, in which the olefination/alkylation process can be finely controlled at room temperature by variation of the reaction conditions. This method shows excellent functional group tolerance, and presents a mild access to the resulting olefination/alkylation products in moderate to good yields.

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14

Liang, Zhongwei, Song Xu, Wenyan Tian, and Ronghua Zhang. "Eosin Y-catalyzed visible-light-mediated aerobic oxidative cyclization of N,N-dimethylanilines with maleimides." Beilstein Journal of Organic Chemistry 11 (April 1, 2015): 425–30. http://dx.doi.org/10.3762/bjoc.11.48.

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A novel and simple strategy for the efficient synthesis of the corresponding tetrahydroquinolines from N,N-dimethylanilines and maleimides using visible light in an air atmosphere in the presence of Eosin Y as a photocatalyst has been developed. The metal-free protocol involves aerobic oxidative cyclization via sp3 C–H bond functionalization process to afford good yields in a one-pot procedure under mild conditions.

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15

Bettadapur, Kiran R., Veeranjaneyulu Lanke, and Kandikere Ramaiah Prabhu. "ChemInform Abstract: Ru(II)-Catalyzed C-H Activation: Ketone-Directed Novel 1,4-Addition of ortho C-H Bond to Maleimides." ChemInform 47, no. 9 (February 2016): no. http://dx.doi.org/10.1002/chin.201609060.

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16

Ohara, Nozomi, Supriya Rej, and Naoto Chatani. "Rh(I)-catalyzed Addition of the ortho C-H Bond in Aryl Sulfonamides to Maleimides." Chemistry Letters 49, no. 9 (September 5, 2020): 1053–57. http://dx.doi.org/10.1246/cl.200353.

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17

Reddy, Keesari N., Medikonda V. Krishna Rao, Balasubramanian Sridhar, and Basi V. Subba Reddy. "Ru(II)‐Catalyzed Hydroarylation of Maleimides with Cyclic N ‐SulfonylKetimines through ortho ‐C‐H Bond Activation." ChemistrySelect 3, no. 18 (May 14, 2018): 5062–65. http://dx.doi.org/10.1002/slct.201800352.

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18

Yuan, Yu-Chao, Marion Goujon, Christian Bruneau, Thierry Roisnel, and Rafael Gramage-Doria. "C–H Bond Alkylation of Cyclic Amides with Maleimides via a Site-Selective-Determining Six-Membered Ruthenacycle." Journal of Organic Chemistry 84, no. 24 (November 25, 2019): 16183–91. http://dx.doi.org/10.1021/acs.joc.9b02690.

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19

Manoharan, Ramasamy, and Masilamani Jeganmohan. "Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition‐Metal‐Catalyzed C‐H Bond Activation." Asian Journal of Organic Chemistry 8, no. 11 (May 10, 2019): 1949–69. http://dx.doi.org/10.1002/ajoc.201900054.

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20

Cheng, Xiaoyu, Baojun Li, Mengsi Zhang, Haotian Lu, Wenbo Wang, Yun Ding, and Aiguo Hu. "Direct functionalization of cyclic ethers with maleimide iodides via free radial-mediated sp3 C–H activation." Chemical Communications 57, no. 39 (2021): 4787–90. http://dx.doi.org/10.1039/d1cc01484f.

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21

He, Qiyuan, Takuma Yamaguchi, and Naoto Chatani. "Rh(I)-Catalyzed Alkylation of ortho-C–H Bonds in Aromatic Amides with Maleimides." Organic Letters 19, no. 17 (August 11, 2017): 4544–47. http://dx.doi.org/10.1021/acs.orglett.7b02135.

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22

Kumar, Rakesh, Rohit Kumar, Devesh Chandra, and Upendra Sharma. "Cp*CoIII–Catalyzed Alkylation of Primary and Secondary C(sp3)-H Bonds of 8-Alkylquinolines with Maleimides." Journal of Organic Chemistry 84, no. 3 (January 8, 2019): 1542–52. http://dx.doi.org/10.1021/acs.joc.8b02974.

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23

Wang, Bing, James F. Hinton, and Peter Pulay. "C−H···O Hydrogen Bond betweenN-Methyl Maleimide and Dimethyl Sulfoxide: A Combined NMR and Ab Initio Study." Journal of Physical Chemistry A 107, no. 23 (June 2003): 4683–87. http://dx.doi.org/10.1021/jp026986b.

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24

Gurram, Ravi Kumar, Manda Rajesh, Maneesh Kumar Reddy Singam, Jagadeesh Babu Nanubolu, and Maddi Sridhar Reddy. "A Sequential Activation of Alkyne and C–H Bonds for the Tandem Cyclization and Annulation of Alkynols and Maleimides through Cooperative Sc(III) and Cp*-Free Co(II) Catalysis." Organic Letters 22, no. 14 (July 7, 2020): 5326–30. http://dx.doi.org/10.1021/acs.orglett.0c01533.

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25

Gurram, Ravi Kumar, Manda Rajesh, Maneesh Kumar Reddy Singam, Jagadeesh Babu Nanubolu, and Maddi Sridhar Reddy. "Correction to “A Sequential Activation of Alkyne and C–H Bonds for the Tandem Cyclization and Annulation of Alkynols and Maleimides through Cooperative Sc(III) and Cp*-Free Co(II) Catalysis”." Organic Letters 22, no. 18 (September 8, 2020): 7408. http://dx.doi.org/10.1021/acs.orglett.0c02807.

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26

Bulatov, Evgeny, Dina Boyarskaya, Tatiana Chulkova, and Matti Haukka. "2,3-Diphenylmaleimide 1-methylpyrrolidin-2-one monosolvate." Acta Crystallographica Section E Structure Reports Online 70, no. 3 (February 8, 2014): o260. http://dx.doi.org/10.1107/s1600536814002372.

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In the title compound, C16H11NO2·C5H9NO, the dihedral angles between the maleimide and phenyl rings are 34.7 (2) and 64.8 (2)°. In the crystal, the 2,3-diphenylmaleimide and 1-methylpyrrolidin-2-one molecules form centrosymmetrical dimersviapairs of strong N—H...O hydrogen bonds and π–π stacking interactions between the two neighboring maleimide rings [centroid–centroid distance = 3.495 (2) Å]. The dimers are further linked by weak C—H...O and C—H...π hydrogen bonds into a three-dimensional framework.

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27

Tian, Ting, An-Shun Dong, Dan Chen, Xian-Ting Cao, and Guannan Wang. "Regioselective C–C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium-catalyzed C–H activation." Organic & Biomolecular Chemistry 17, no. 33 (2019): 7664–68. http://dx.doi.org/10.1039/c9ob01539f.

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28

Schapin, Igor Yu, and Vladimir S. Mastryukov. "Inverse “bond length/bond angle” relationship: CH versus HCH." Journal of Molecular Structure 268, no. 1-3 (April 1992): 307–10. http://dx.doi.org/10.1016/0022-2860(92)85079-v.

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29

Park, Hyunjin, Jineun Kim, Eunjin Kwon, and Tae Ho Kim. "Crystal structure of flumioxazin." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (September 17, 2015): o768. http://dx.doi.org/10.1107/s2056989015017223.

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The title compound {systematic name: 2-[7-fluoro-3,4-dihydro-3-oxo-4-(prop-2-yn-1-yl)-2H-1,4-benzoxazin-6-yl]-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione}, C19H15FN2O4, is a dicarboximide herbicide. The dihedral angle between the maleimide and benzene ring planes is 66.13 (5)°. In the crystal, C—H...O and C—H...F hydrogen bonds and weak C—H...π interactions [3.5601 (19) Å] link adjacent molecules, forming two-dimensional networks extending parallel to the (110) plane.

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30

Said, Awad I., and Talaat I. El-Emary. "Diastereoselective synthesis of atropisomeric pyrazolyl pyrrolo[3,4-d]isoxazolidines via pyrazolyl nitrone cycloaddition to facially divergent maleimides: intensive NMR and DFT studies." RSC Advances 10, no. 2 (2020): 845–50. http://dx.doi.org/10.1039/c9ra10039c.

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Diastereoselective pyrazole-based atropisomeric cycloadducts were formed by cycloaddition of a pyrazole-based nitrone and maleimides with restricted rotation around C–N bond caused by bulk ortho substitution.

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31

Hirata, Toshifumi, Asuka Takarada, Mohamed-Elamir F. Hegazy, Yuya Sato, Akihito Matsushima, Yoko Kondo, Ayako Matsuki, and Hiroki Hamada. "Hydrogenation of the C–C double bond of maleimides with cultured plant cells." Journal of Molecular Catalysis B: Enzymatic 32, no. 4 (February 2005): 131–34. http://dx.doi.org/10.1016/j.molcatb.2004.11.008.

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32

Pi, Chao, Yaping Qu, Xiuling Cui, and Yangjie Wu. "Silver-Catalyzed C—H Alkylation of 2-Arylindoles with Maleimides." Chinese Journal of Organic Chemistry 40, no. 3 (2020): 740. http://dx.doi.org/10.6023/cjoc201907040.

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33

Li, Bang, Qi Mao, Jia Zhou, Feng Liu, and Na Ye. "HFIP-promoted Michael reactions: direct para-selective C–H activation of anilines with maleimides." Organic & Biomolecular Chemistry 17, no. 8 (2019): 2242–46. http://dx.doi.org/10.1039/c8ob03073a.

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34

Davies, H. M. L., and D. Morton. "ChemInform Abstract: C-C Bond Formation by C-H Bond Activation." ChemInform 42, no. 42 (September 27, 2011): no. http://dx.doi.org/10.1002/chin.201142249.

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35

Jing, Hua-Qing, Jon C. Antilla, and Hong-Liang Li. "Regioselective C-H Borylation of C (sp2)-H Bond." Madridge Journal of Novel Drug Research 3, no. 1 (February 26, 2019): 114–19. http://dx.doi.org/10.18689/mjndr-1000117.

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36

Zhao, Hua, Taimin Wang, Zhineng Qing, and Hongbin Zhai. "Cobalt-catalyzed 2-(1-methylhydrazinyl)pyridine-assisted cyclization of thiophene-2-carbohydrazides with maleimides: efficient synthesis of thiophene-fused pyridones." Chemical Communications 56, no. 41 (2020): 5524–27. http://dx.doi.org/10.1039/d0cc01582b.

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A cobalt-catalyzed direct C–H/N–H functionalization of thiophene-2-carbohydrazides with maleimides by utilizing 2-(1-methylhydrazinyl)pyridine (MHP) as an easily removable bidentate directing group has been developed.

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37

Ghosh, Asim Kumar, Sadhanendu Samanta, Payel Ghosh, Sukanya Neogi, and Alakananda Hajra. "Regioselective hydroarylation and arylation of maleimides with indazoles via a Rh(iii)-catalyzed C–H activation." Organic & Biomolecular Chemistry 18, no. 16 (2020): 3093–97. http://dx.doi.org/10.1039/d0ob00353k.

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38

WILSON, ELIZABETH K. "EXPLAINING C-H BOND STRENGTHS." Chemical & Engineering News 84, no. 10 (March 6, 2006): 65. http://dx.doi.org/10.1021/cen-v084n010.p065.

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39

Meng, Guangrong, and Michal Szostak. "Rhodium-Catalyzed C–H Bond Functionalization with Amides by Double C–H/C–N Bond Activation." Organic Letters 18, no. 4 (February 8, 2016): 796–99. http://dx.doi.org/10.1021/acs.orglett.6b00058.

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40

Zhao, Hua, Xiaoru Shao, Taimin Wang, Shengxian Zhai, Shuxian Qiu, Cheng Tao, Huifei Wang, and Hongbin Zhai. "A 2-(1-methylhydrazinyl)pyridine-directed C–H functionalization/spirocyclization cascade: facile access to spirosuccinimide derivatives." Chemical Communications 54, no. 39 (2018): 4927–30. http://dx.doi.org/10.1039/c8cc01774c.

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41

Bettadapur, Kiran R., Mahadev Sharanappa Sherikar, Veeranjaneyulu Lanke, and Kandikere Ramaiah Prabhu. "RhIII -Catalyzed C−H Activation: Mizoroki-Heck-Type Reaction of Maleimides." Asian Journal of Organic Chemistry 7, no. 7 (May 30, 2018): 1338–42. http://dx.doi.org/10.1002/ajoc.201800193.

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42

Sharma, Satyasheel, Sang Hoon Han, Hyeim Jo, Sangil Han, Neeraj Kumar Mishra, Miji Choi, Taejoo Jeong, Jihye Park, and In Su Kim. "Rhodium-Catalyzed Vinylic C-H Functionalization of Enol Carbamates with Maleimides." European Journal of Organic Chemistry 2016, no. 21 (June 24, 2016): 3611–18. http://dx.doi.org/10.1002/ejoc.201600558.

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43

Narayan, Rishikesh, Kiran Matcha, and Andrey P. Antonchick. "Metal-Free Oxidative CC Bond Formation through CH Bond Functionalization." Chemistry - A European Journal 21, no. 42 (August 3, 2015): 14678–93. http://dx.doi.org/10.1002/chem.201502005.

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44

Zheng, Qing-Zhong, and Ning Jiao. "Ag-catalyzed C–H/C–C bond functionalization." Chemical Society Reviews 45, no. 16 (2016): 4590–627. http://dx.doi.org/10.1039/c6cs00107f.

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45

Cubbage, Kara L, Andrew J Orr-Ewing, and Kevin I Booker-Milburn. "First Higher-Order Photocycloaddition to a CN Bond: 1,3-Diazepines from Maleimides." Angewandte Chemie International Edition 48, no. 14 (March 23, 2009): 2514–17. http://dx.doi.org/10.1002/anie.200805846.

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46

Cubbage, Kara L, Andrew J Orr-Ewing, and Kevin I Booker-Milburn. "First Higher-Order Photocycloaddition to a CN Bond: 1,3-Diazepines from Maleimides." Angewandte Chemie 121, no. 14 (March 23, 2009): 2552–55. http://dx.doi.org/10.1002/ange.200805846.

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47

Zhao, Yating, and Wujiong Xia. "Photochemical C–H bond coupling for (hetero)aryl C(sp2)–C(sp3) bond construction." Organic & Biomolecular Chemistry 17, no. 20 (2019): 4951–63. http://dx.doi.org/10.1039/c9ob00244h.

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This review highlights the recent advances in photochemical (hetero)aryl C(sp²)–C(sp³) bond construction via C–H bond coupling such as (hetero)arylation of C(sp³)–H bonds and alkylation of (hetero)aryl C(sp²)–H bonds.

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48

Wang, Xiao, Ming-Zhu Lu, and Teck-Peng Loh. "Transition-Metal-Catalyzed C–C Bond Macrocyclization via Intramolecular C–H Bond Activation." Catalysts 13, no. 2 (February 17, 2023): 438. http://dx.doi.org/10.3390/catal13020438.

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Macrocycles are commonly synthesized via late-stage macrolactamization and macrolactonization. Strategies involving C–C bond macrocyclization have been reported, and examples include the transition-metal-catalyzed ring-closing metathesis and coupling reactions. In this mini-review, we summarize the recent progress in the direct synthesis of polyketide and polypeptide macrocycles using a transition-metal-catalyzed C–H bond activation strategy. In the first part, rhodium-catalyzed alkene–alkene ring-closing coupling for polyketide synthesis is described. The second part summarizes the synthesis of polypeptide macrocycles. The activation of indolyl and aryl C(sp2)–H bonds followed by coupling with various coupling partners such as aryl halides, arylates, and alkynyl bromide is then documented. Moreover, transition-metal-catalyzed C–C bond macrocyclization reactions via alkyl C(sp3)–H bond activation are also included. We hope that this mini-review will inspire more researchers to explore new and broadly applicable strategies for C–C bond macrocyclization via intramolecular C–H activation.

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49

Ping, Yuanyuan, Qiuping Ding, and Yiyuan Peng. "Advances in C–CN Bond Formation via C–H Bond Activation." ACS Catalysis 6, no. 9 (August 10, 2016): 5989–6005. http://dx.doi.org/10.1021/acscatal.6b01632.

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50

Esteruelas, Miguel A., Montserrat Oliván, and Andrea Vélez. "POP–Rhodium-Promoted C–H and B–H Bond Activation and C–B Bond Formation." Organometallics 34, no. 10 (May 2015): 1911–24. http://dx.doi.org/10.1021/acs.organomet.5b00176.

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