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Journal articles on the topic 'C(sp2)−H Alkylation'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 September 2023

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1

Manna, Madhu Sudan, and Santanu Mukherjee. "Organocatalytic Enantioselective Formal C(sp2)–H Alkylation." Journal of the American Chemical Society 137, no. 1 (2015): 130–33. http://dx.doi.org/10.1021/ja5117556.

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2

Sarkar, Rahul, and Santanu Mukherjee. "Iridium-catalyzed enantioselective olefinic C(sp2)–H allylic alkylation." Chemical Science 12, no. 8 (2021): 3070–75. http://dx.doi.org/10.1039/d0sc06208a.

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The first iridium-catalyzed enantioselective allylic alkylation of an olefinic C(sp<sup>2</sup>)–H bond – that of an α,β-unsaturated carbonyl compound, is developed in cooperation with Lewis base catalysis.

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3

Zhu, Ru-Yi, Jian He, Xiao-Chen Wang, and Jin-Quan Yu. "Ligand-Promoted Alkylation of C(sp3)–H and C(sp2)–H Bonds." Journal of the American Chemical Society 136, no. 38 (2014): 13194–97. http://dx.doi.org/10.1021/ja508165a.

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4

Gustafson, Jeffrey, Andrew Dinh, Ryan Noorbehesht, et al. "Toward a Catalytic Atroposelective Synthesis of Diaryl Ethers Through C(sp2)–H Alkylation with Nitroalkanes." Synlett 29, no. 16 (2018): 2155–60. http://dx.doi.org/10.1055/s-0037-1609581.

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We report studies toward a small-molecule-catalytic approach to access atropisomeric diaryl ethers that proceeds through a C(sp2)–H alkylation using nitroalkanes as the alkyl source. A quaternary ammonium salt derived from quinine, containing a sterically hindered urea at the C-9 position, was found to effect atroposelective C(sp2)–H alkylation with moderate to good enantioselectivities across several naphthoquinone-containing diaryl ethers. Products could then be isolated in >95:5 er after one round of trituration. For several substrates that were evaluated, we obtained nitroethylated prod

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5

Sarkar, Rahul, and Santanu Mukherjee. "Correction: Iridium-catalyzed enantioselective olefinic C(sp2)–H allylic alkylation." Chemical Science 12, no. 8 (2021): 3076. http://dx.doi.org/10.1039/d1sc90022f.

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6

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(sp<sup>2</sup>)–C(sp<sup>3</sup>) bond construction via C–H bond coupling such as (hetero)arylation of C(sp<sup>3</sup>)–H bonds and alkylation of (hetero)aryl C(sp<sup>2</sup>)–H bonds.

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7

Singh, Swati, Neha Dagar, and Sudipta Raha Roy. "Photoinduced ligand to metal charge transfer enabling cerium mediated decarboxylative alkylation of quinoxalin-2(1H)-ones." Chemical Communications 58, no. 23 (2022): 3831–34. http://dx.doi.org/10.1039/d2cc00840h.

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Photo-induced decarboxylative alkylation utilizing an inexpensive cerium catalyst has been discussed. Here, we utilized unactivated carboxylic acids for the regiospecific alkylation of the C(sp2)–H bond of heterocycles.

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8

Manna, Madhu Sudan, and Santanu Mukherjee. "ChemInform Abstract: Organocatalytic Enantioselective Formal C(sp2)-H Alkylation." ChemInform 46, no. 27 (2015): no. http://dx.doi.org/10.1002/chin.201527029.

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9

Catellani, Marta, Federica Cugini, and Domenico Tiefenthaler. "New pathways of site selective aromatic alkylation of palladium complexes: fragmentation to arenes vs. ring closure to hexahydromethano-fluorenes or -phenanthrenes." Canadian Journal of Chemistry 79, no. 5-6 (2001): 742–51. http://dx.doi.org/10.1139/v01-047.

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Dimeric arylbicycloheptylpalladium halide complexes of type 1 undergo selective alkylation at the aromatic site by reaction with allyl, styryl, and benzyl bromides (RBr) via hexahydromethanopalladafluorenes (2). Ring closure of the resulting palladium complex (7) on sp2 and sp3 C-H bonds of a suitable R group then occurs with formation of hexahydromethanophenanthrene or hexahydromethanofluorene derivatives. Alternatively, substituted arenes derived from bicycloheptene deinsertion are formed. In some cases the latter can be obtained in substantial amounts when methyl isonicotinate is used as li

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10

Bertho, Sylvain, Ismaël Dondasse, Pascal Retailleau, Cyril Nicolas та Isabelle Gillaizeau. "β-C(sp2)–H alkylation of enamides using xanthate chemistry". New Journal of Chemistry 44, № 17 (2020): 7129–41. http://dx.doi.org/10.1039/d0nj01209b.

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11

Sarkar, Rahul, and Santanu Mukherjee. "Catalytic Enantioselective Desymmetrization of Norbornenoquinones via C(sp2)–H Alkylation." Organic Letters 18, no. 23 (2016): 6160–63. http://dx.doi.org/10.1021/acs.orglett.6b03168.

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12

Kim, Ye Lim, Sun-a. Park, and Ju Hyun Kim. "Cobalt-Catalyzed Direct C(sp2 )-H Alkylation with Unactivated Alkenes." European Journal of Organic Chemistry 2020, no. 26 (2020): 4026–30. http://dx.doi.org/10.1002/ejoc.202000565.

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13

Zhu, Ru-Yi, Jian He, Xiao-Chen Wang, and Jin-Quan Yu. "ChemInform Abstract: Ligand-Promoted Alkylation of C(sp3)-H and C(sp2)-H Bonds." ChemInform 46, no. 15 (2015): no. http://dx.doi.org/10.1002/chin.201515050.

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14

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

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Recent advances in the direct β-C(sp<sup>2</sup>)–H functionalization of enamides, mainly including arylation, alkenylation, alkynylation, alkylation, acylation, sulfonylation, phosphorylation, and others, are reported.

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15

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 (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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16

Xie, Hui, Jin-Yi Liang, Zhuo-Jun Huang, et al. "Rh(iii)-Catalyzed tandem C(sp²)–H allylation/N-alkylation annulation of arene amides with 2-alkylidenetrimethylene carbonates." Organic Chemistry Frontiers 8, no. 23 (2021): 6585–90. http://dx.doi.org/10.1039/d1qo01129d.

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A Rh(iii)-catalyzed tandem C(sp2)–H allylation/N-alkylation annulation reaction of arene amides employing 5-methylene-1,3-dioxan-2-one as an efficient allyl source has been disclosed for the first time.

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17

Monks, Brendan M., Erin R. Fruchey, and Silas P. Cook. "Iron-Catalyzed C(sp2)H Alkylation of Carboxamides with Primary Electrophiles." Angewandte Chemie International Edition 53, no. 41 (2014): 11065–69. http://dx.doi.org/10.1002/anie.201406594.

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18

Monks, Brendan M., Erin R. Fruchey, and Silas P. Cook. "Iron-Catalyzed C(sp2)H Alkylation of Carboxamides with Primary Electrophiles." Angewandte Chemie 126, no. 41 (2014): 11245–49. http://dx.doi.org/10.1002/ange.201406594.

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19

Sun, Meng, Xiang-Xiang Chen, Jiang-Tao Ren, et al. "Cobalt(III)-Catalyzed 1,4-Addition of C(sp3)–H Bonds to Maleimides." Synlett 29, no. 12 (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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20

Pandey, Ganesh, Sandip Kumar Tiwari, Bhawana Singh, Kumar Vanka, and Shailja Jain. "p-Selective (sp2)-C–H functionalization for an acylation/alkylation reaction using organic photoredox catalysis." Chemical Communications 53, no. 91 (2017): 12337–40. http://dx.doi.org/10.1039/c7cc07529d.

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p-Selective (sp<sup>2</sup>)-C–H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.

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21

Wen, Jiangwei, Fan Zhang, Wenyan Shi, and Aiwen Lei. "Metal-Free Direct Alkylation of Ketene Dithioacetals by Oxidative C(sp2 )−H/C(sp3 )−H Cross-Coupling." Chemistry - A European Journal 23, no. 37 (2017): 8814–17. http://dx.doi.org/10.1002/chem.201701664.

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22

Tsuzuki, Saori, Shunya Sakurai, Akira Matsumoto, Taichi Kano, and Keiji Maruoka. "Ni-Catalyzed C(sp2)–H alkylation of N-quinolylbenzamides using alkylsilyl peroxides as structurally diverse alkyl sources." Chemical Communications 57, no. 64 (2021): 7942–45. http://dx.doi.org/10.1039/d1cc02983e.

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23

Kumar, Nivesh, Santanu Ghosh, Subhajit Bhunia, and Alakesh Bisai. "Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C–H and sp3 C–H bonds." Beilstein Journal of Organic Chemistry 12 (June 8, 2016): 1153–69. http://dx.doi.org/10.3762/bjoc.12.111.

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The synthesis of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudo benzylic position has been achieved via a ‘transition-metal-free’ intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon–carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of β-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for this reaction.

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24

Luo, Yan-Long, Hui-Zhen Du, and Bing-Tao Guan. "Alkali-amide-catalyzed divergent sp2 and sp3 C–H bonds alkylation of alkylthiophenes with alkenes." Organic Chemistry Frontiers 8, no. 15 (2021): 4171–76. http://dx.doi.org/10.1039/d1qo00627d.

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Divergent sp<sup>2</sup> and sp<sup>3</sup> C–H bonds alkylation of alkylthiophenes was achieved selectively with LDA and KHMDS catalysts, providing not only atom-economical synthesis approaches but also some insights in the different behaviours of the alkali amides.

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25

Pérez-Temprano, Mónica H. "Engineering a mild and site-selective Ru-catalyzed C(sp2)–H alkylation protocol." Chem Catalysis 1, no. 3 (2021): 497–99. http://dx.doi.org/10.1016/j.checat.2021.07.006.

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26

Xu, Bing, Danting Ji, Lizuo Wu, et al. "Palladium/Xu-Phos-catalyzed enantioselective cascade Heck/remote C(sp2) –H alkylation reaction." Chem 8, no. 3 (2022): 836–49. http://dx.doi.org/10.1016/j.chempr.2021.12.019.

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27

Monks, Brendan M., Erin R. Fruchey, and Silas P. Cook. "ChemInform Abstract: Iron-Catalyzed C(sp2)-H Alkylation of Carboxamides with Primary Electrophiles." ChemInform 46, no. 12 (2015): no. http://dx.doi.org/10.1002/chin.201512071.

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28

Du, Yingying, Fang Yao та Mingzhong Cai. "Highly para-selective C‒H alkylation of unactivated arenes with α-aryl-α-diazoesters catalyzed by gold(I) immobilized on MCM-41". Journal of Chemical Research 44, № 3-4 (2019): 174–80. http://dx.doi.org/10.1177/1747519819893878.

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The heterogeneous gold(I)-catalyzed highly para-selective C(sp2)–H bond alkylation of benzene derivatives with α-aryl-α-diazoesters possessing electron-withdrawing substituents on the aryl rings are achieved. The reactions proceed under mild conditions in good to excellent yields by using an MCM-41-anchored diphenylphosphine gold(I) complex [MCM-41-PPh2-AuOTf] as a recyclable catalyst.

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29

Jin, Hongming, Zhengbo Zhu, Ning Jin, Jin Xie, Yixiang Cheng, and Chengjian Zhu. "CO-enabled rhenium hydride catalyst for directed C(sp2)–H bond alkylation with olefins." Organic Chemistry Frontiers 2, no. 4 (2015): 378–82. http://dx.doi.org/10.1039/c4qo00329b.

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30

Zhao, Yingsheng, and Gong Chen. "Palladium-Catalyzed Alkylation ofortho-C(sp2)–H Bonds of Benzylamide Substrates with Alkyl Halides." Organic Letters 13, no. 18 (2011): 4850–53. http://dx.doi.org/10.1021/ol201930e.

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31

Prieto, Alexis, Romain Melot, Didier Bouyssi, and Nuno Monteiro. "Palladium-Catalyzed C(sp2 )−H Alkylation of Aldehyde-Derived Hydrazones with Functionalized Difluoromethyl Bromides." Angewandte Chemie International Edition 55, no. 5 (2015): 1885–89. http://dx.doi.org/10.1002/anie.201510334.

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32

Prieto, Alexis, Romain Melot, Didier Bouyssi, and Nuno Monteiro. "Palladium-Catalyzed C(sp2 )−H Alkylation of Aldehyde-Derived Hydrazones with Functionalized Difluoromethyl Bromides." Angewandte Chemie 128, no. 5 (2015): 1917–21. http://dx.doi.org/10.1002/ange.201510334.

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33

Wang, Xie, Peipei Xie, Renhua Qiu, et al. "Nickel-catalysed direct alkylation of thiophenes via double C(sp3)–H/C(sp2)–H bond cleavage: the importance of KH2PO4." Chemical Communications 53, no. 59 (2017): 8316–19. http://dx.doi.org/10.1039/c7cc04252c.

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34

Xu, Xiangsheng, Zhiyan Hu, Yucai Tang, Shan Zhang, Xiaoqing Li, and Xiaohua Du. "MnO2-Catalyzed Oxidative Alkylation of Enamides with Ethers via C(sp3)–H/C(sp2)–H Cross-Dehydrogenative Coupling and Hydrolysis Sequence." Synlett 26, no. 18 (2015): 2557–60. http://dx.doi.org/10.1055/s-0035-1560180.

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35

Jagtap, Rahul A., Pragnya Paramita Samal, C. P. Vinod, Sailaja Krishnamurty, and Benudhar Punji. "Iron-Catalyzed C(sp2)–H Alkylation of Indolines and Benzo[h]quinoline with Unactivated Alkyl Chlorides through Chelation Assistance." ACS Catalysis 10, no. 13 (2020): 7312–21. http://dx.doi.org/10.1021/acscatal.0c02030.

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36

Li, Dan-Dan, Liang-Feng Niu, Zhi-Yu Ju, Zhihong Xu, and Changzeng Wu. "Palladium-Catalyzed C(sp2)-H Bond Alkylation of Ketoximes by Using the Ring-Opening of Epoxides." European Journal of Organic Chemistry 2016, no. 18 (2016): 3090–96. http://dx.doi.org/10.1002/ejoc.201600335.

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37

Hu, Zhiyan, Yucai Tang, Shan Zhang, Xiaoqing Li, Xiaohua Du, and Xiangsheng Xu. "ChemInform Abstract: MnO2-Catalyzed Oxidative Alkylation of Enamides with Ethers via C(sp3)-H/C(sp2)-H Cross-Dehydrogenative Coupling and Hydrolysis Sequence." ChemInform 47, no. 13 (2016): no. http://dx.doi.org/10.1002/chin.201613170.

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38

Mitra, Mainak, Debojyoti Mukherjee, Ujjwal Mandal, and Albert A. Shteinman. "Palladium(II)-assisted ortho alkylation of C(sp2)-H bonds in substituted azobenzenes with simple alkyl halides." Journal of Coordination Chemistry 71, no. 23 (2018): 3824–35. http://dx.doi.org/10.1080/00958972.2018.1545089.

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39

Guo, Jing-Yu, Ting Guan, Ji-Yu Tao, Kai Zhao, and Teck-Peng Loh. "Stereoselective C(sp2)–H Alkylation of Enamides with Unactivated Aliphatic Carboxylic Acids via Decarboxylative Cross-Coupling Reactions." Organic Letters 21, no. 20 (2019): 8395–99. http://dx.doi.org/10.1021/acs.orglett.9b03169.

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40

Li, Feng, Yirong Zhou, Heng Yang, Dandan Liu, Bing Sun, and Fang-Lin Zhang. "Assembly of Diverse Spirocyclic Pyrrolidines via Transient Directing Group Enabled Ortho-C(sp2)–H Alkylation of Benzaldehydes." Organic Letters 20, no. 1 (2017): 146–49. http://dx.doi.org/10.1021/acs.orglett.7b03502.

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41

Zhao, Yingsheng, and Gong Chen. "ChemInform Abstract: Palladium-Catalyzed Alkylation of ortho-C(sp2)-H Bonds of Benzylamide Substrates with Alkyl Halides." ChemInform 43, no. 3 (2011): no. http://dx.doi.org/10.1002/chin.201203061.

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42

Xu, Wentao, Ning Wang, Mengye Zhang, and Daqing Shi. "Ruthenium-Catalyzed C(sp2)-H Alkenylation and Alkylation of 1-Benzyl-1H-pyrazole under Assistance of Pyrazole Group." Chinese Journal of Organic Chemistry 39, no. 6 (2019): 1735. http://dx.doi.org/10.6023/cjoc201901005.

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43

Nadres, Enrico T., Gerson Ivan Franco Santos, Dmitry Shabashov, and Olafs Daugulis. "Scope and Limitations of Auxiliary-Assisted, Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 C–H Bonds." Journal of Organic Chemistry 78, no. 19 (2013): 9689–714. http://dx.doi.org/10.1021/jo4013628.

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44

McLarney, Brett D., Marchello A. Cavitt, Theodore M. Donnell, Djamaladdin G. Musaev та Stefan France. "RhII-Catalyzed β-C(sp2)−H Alkylation of Enol Ethers, Enamides and Enecarbamates with α-Diazo Dicarbonyl Compounds". Chemistry - A European Journal 23, № 5 (2016): 1129–35. http://dx.doi.org/10.1002/chem.201604518.

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45

Wang, Guang-Zu, Ming-Chen Fu, Bin Zhao, and Rui Shang. "Photocatalytic decarboxylative alkylations of C(sp3)-H and C(sp2)-H bonds enabled by ammonium iodide in amide solvent." Science China Chemistry 64, no. 3 (2021): 439–44. http://dx.doi.org/10.1007/s11426-020-9905-1.

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46

Pollice, Robert, Navid Dastbaravardeh, Nada Marquise, Marko D. Mihovilovic, and Michael Schnürch. "Mechanistic and Kinetic Studies of the Direct Alkylation of Benzylic Amines: A Formal C(sp3)–H Activation Proceeds Actually via a C(sp2)–H Activation Pathway." ACS Catalysis 5, no. 2 (2014): 587–95. http://dx.doi.org/10.1021/cs501924c.

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47

Dong, Xunqing, Qun Li, Guigen Li, and Hongjian Lu. "Cobalt-Catalyzed Secondary Alkylation of Arenes and Olefins with Alkyl Ethers through the Cleavage of C(sp2)–H and C(sp3)–O Bonds." Journal of Organic Chemistry 83, no. 21 (2018): 13402–13. http://dx.doi.org/10.1021/acs.joc.8b02197.

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48

Bagle, Pradip N., Manoj V. Mane, Shashank P. Sancheti, et al. "Gold(I)-Catalyzed Hydroxy Group Assisted C(sp2)–H Alkylation of Enaminones with Diazo Compounds To Access 3-Alkyl Chromones." Organic Letters 21, no. 1 (2018): 335–39. http://dx.doi.org/10.1021/acs.orglett.8b03989.

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49

Gartia, Yashraj, Punnamchandar Ramidi, Darin E. Jones, Sharon Pulla, and Anindya Ghosh. "Nickel Complex Catalyzed Efficient Activation of sp3 and sp2 C–H Bonds for Alkylation and Arylation of Oxygen Containing Heterocyclic Molecules." Catalysis Letters 144, no. 3 (2013): 507–15. http://dx.doi.org/10.1007/s10562-013-1170-8.

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50

Wang, Siyu, Lianyou Zheng, Shutao Wang, Shulin Ning, Zhuoqi Zhang, and Jinbao Xiang. "Direct C(sp³)–H allylation of 2-alkylpyridines with Morita–Baylis–Hillman carbonates via a tandem nucleophilic substitution/aza-Cope rearrangement." Beilstein Journal of Organic Chemistry 17 (October 1, 2021): 2505–10. http://dx.doi.org/10.3762/bjoc.17.167.

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A base- and catalyst-free C(sp3)–H allylic alkylation of 2-alkylpyridines with Morita–Baylis–Hillman (MBH) carbonates is described. A plausible mechanism of the reaction might involve a tandem SN2’ type nucleophilic substitution followed by an aza-Cope rearrangement. Various alkyl substituents on 2-alkylpyridines were tolerated in the reaction to give the allylation products in 26–91% yields. The developed method provides a straightforward and operational simple strategy for the allylic functionalization of 2-alkypyridine derivatives.

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