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Journal articles on the topic 'C-alkylation'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Merkhatuly, N., A. N. Iskanderov, А. Т. Omarova, P. Vojtíšek та S. K. Zhokizhanova. "The reaction of C-alkylation of eudesmanolide (–)-α-santonin". Bulletin of the Karaganda University. "Chemistry" series 94, № 2 (2019): 14–18. http://dx.doi.org/10.31489/2019ch2/14-18.

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2

Gurgui-Ionescu, Catalina, Loïc Toupet, Lycia Uttaro, Alain Fruchier, and Véronique Barragan-Montero. "O-Alkylation versus C-alkylation under Mitsunobu conditions." Tetrahedron 63, no. 38 (2007): 9345–53. http://dx.doi.org/10.1016/j.tet.2007.07.002.

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3

Hume, Paul A., Margaret A. Brimble, and Jóhannes Reynisson. "The Bioreductive Alkylation of DNA by Kalafungin: A Theoretical Investigation." Australian Journal of Chemistry 65, no. 4 (2012): 402. http://dx.doi.org/10.1071/ch12018.

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The thermochemical cascades for the bioreductive alkylation of DNA by kalafungin were calculated using density functional theory (DFT). Guanine (G) was used as a model nucleotide. According to the calculations both one- and two-electron reduction of kalafungin is possible in vivo. Furthermore, a clear pathway was found for both mono- and bis-alkylations of G with the former favoured. Alkylation at C-8 position of G is considerably more exothermic than on the N2-exocyclic amine. In the absence of experimentally identified adduct structures of kalafungin, the results presented here support the i

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4

Dong, Guangbin, Hee Lim та Dong Xing. "Transition-Metal-Catalyzed Ketone α-Alkylation and Alkenylation with Simple Alkenes and Alkynes through a Dual Activation Strategy". Synlett 30, № 06 (2018): 674–84. http://dx.doi.org/10.1055/s-0037-1610315.

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In this personal account, we summarize our investigations on the α-alkylation and α-alkenylation reactions of ketones with nonactivated alkenes and alkynes, respectively. The serendipitous discovery of C–H alkylation/alkenylation of cyclic 1,2-diketones provided a proof of concept for a dual activation strategy. Extension to the α-alkylation and α-alkenylation of regular ketones was achieved by using 7-azaindoline as a bifunctional ligand. Subsequently, intramolecular coupling between ketones and olefins was achieved with Rh- and Ru-based systems, respectively. Finally, branched-selective α-a

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5

Horňáček, Michal, Miroslava Bérešová, and Pavol Hudec. "An Environmentally Friendly Catalyst for Aromatic Hydrocarbons Alkylations with 1-alkenes." WSEAS TRANSACTIONS ON ENVIRONMENT AND DEVELOPMENT 20 (December 16, 2024): 835–43. https://doi.org/10.37394/232015.2024.20.78.

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Nowadays, the alkylation of aromatic compounds using 1-alkenes is still conducted in industrial applications using Friedel-Crafts alkylations. The most commonly used catalysts are aluminum chloride (AlCl3) and hydrofluoric acid (HF), both of which pose significant environmental concerns. An alternative approach involves the use of solid acid catalysts, specifically zeolites, which may offer a more environmentally acceptable option. In this study, the alkylation of toluene with 1-decene was performed in a batch reactor under autogenous pressure in the liquid phase at a temperature of 100 °C. Ze

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6

Dehmlow, Eckehard V., and Sabine Schrader. "Notizen: Influence of Counter Ion Structure on the Direction of the Phase Transfer Catalytic Methylation of an Enol [1]." Zeitschrift für Naturforschung B 45, no. 3 (1990): 409–12. http://dx.doi.org/10.1515/znb-1990-0320.

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Phase transfer catalytic (PTC) methylations of deoxybenzoin by dimethyl sulfate can be steered towards enol ether formation by large, sterically shielded ammonium ions or – more strongly – by large highly delocalized phospho-iminium (and presumably other large) cations. The C-alkylation direction is favoured by small, hard ammonium ions of the type RNMe3+ and by crown ethers, particularly benzo-crowns. O/C ratios can be varied between 0,75 and 63, the largest effects so far reported for ambident anions. These results should give guide-lines for alkylations of other ambident ions.

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7

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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8

Yang, Xinglin, Gang Shan, Zimo Yang, et al. "One-pot synthesis of quaternary carbon centered cyclobutanes via Pd(ii)-catalyzed cascade C(sp3)–H activations." Chemical Communications 53, no. 9 (2017): 1534–37. http://dx.doi.org/10.1039/c6cc06897a.

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A novel approach toward quaternary carbon centered cyclobutanes through Pd(ii)-catalyzed sequential intramolecular methylene C–H alkylation and intermolecular methine C–H bond arylation, alkenylation, alkylation, alkynylation, allylation, benzylation or alkoxylation is described.

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9

Xiong, Tao, Qian Zhang, and Qian Zhang. "Transition-Metal-Catalyzed Alkylation of Polyfluoroarenes through C–F Bond Cleavage." Synlett 32, no. 14 (2021): 1379–84. http://dx.doi.org/10.1055/a-1479-8264.

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AbstractThe polyfluoroarenes are a subgroup of organofluorines that are widely utilized in both medicinal chemistry and materials science. We briefly summarize recent advances in the synthesis of these important compounds, with particular attention to our recent CuH-catalyzed defluorinative alkylation of polyfluoroarenes with alkenes in a highly site-selective C–F bond-cleavage fashion.1 Introduction2 Transition-Metal-Catalyzed Alkylation through Selective C–F Bond Cleavage3 CuH-Catalyzed Defluorinative Alkylation of Polyfluoroarenes with Alkenes4 Summary and Outlook

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10

Wu, Jie, Dejiang Huang, Yuannian Zhang, and Xin Yang. "Aerobic C–H Functionalization Using Pyrenedione as the Photocatalyst." Synthesis 52, no. 17 (2020): 2512–20. http://dx.doi.org/10.1055/s-0040-1707135.

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We disclose a visible-light-promoted aerobic alkylation of activated C(sp3)–H bonds using pyrenedione (PYD) as the photocatalyst. Direct C–H bond alkylation of tetrahydrofuran with alkylidenemalononitriles is accomplished in over 90% yield in the presence of 5 mol% of PYD and 18 W blue LED light under ambient conditions. The substrate scope is extended to ethers, thioethers, and allylic C–H bonds in reactions with various electrophilic Michael acceptors. The catalytic turnover process is facilitated by oxygen. Our work represents the first example of using PYD as a photocatalyst to promote C(s

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11

Wang, Xiaoling, Xiaoming Ji, Changdong Shao, Yu Zhang, and Yanghui Zhang. "Palladium-catalyzed C–H alkylation of 2-phenylpyridines with alkyl iodides." Organic & Biomolecular Chemistry 15, no. 26 (2017): 5616–24. http://dx.doi.org/10.1039/c7ob01232b.

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Palladium-catalyzed C–H alkylation reaction of 2-phenylpyridines with alkyl iodides has been successfully developed. The palladacycles obtained from 2-phenylpyridines acted as the key intermediates in the alkylation reaction.

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12

De Munck, Lode, Carlos Vila, Carolina Pons та José Pedro. "Synthesis of Multisubstituted 1,4-Dihydrobenzoxazin-2-ones through a One-Pot Nucleophilic N-Alkylation/C-Alkylation of Cyclic α-Imino Esters". Synthesis 49, № 12 (2017): 2683–90. http://dx.doi.org/10.1055/s-0036-1588742.

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A nucleophilic N-alkylation of 2-oxobenzoxazine-2-carboxylates with organozinc reagents with good selectivities and in moderate to good yields is described. Moreover, the synthesis of multisubstituted 1,4-dihydrobenzoxazine-2-ones bearing a tetrasubstituted carbon atom via a one-pot N-alkylation/C-alkylation reactions is reported.

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13

Li, Wenjuan, Huihang Cheng, Huabo Han та ін. "Novel Brønsted Acid Catalyzed C-C Bond Activation and α-Alkylation of Ketones". Molecules 29, № 17 (2024): 4266. http://dx.doi.org/10.3390/molecules29174266.

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A novel approach for the α-alkylation of ketones was developed using Brønsted acid-catalyzed C-C bond cleavage. Both aromatic and aliphatic ketones reacted smoothly with 2-substituted 1,3-diphenylpropane-1,3-diones to afford α-alkylation products with high yields and with excellent regioselectivity, in which the 1,3-dicarbonyl group acted as a leaving group in the presence of the catalyst TfOH. Mechanism experiments showed that the β-C-C bond cleavage of diketone and the shift of the equilibrium towards the enol formation from ketone are driving forces that induce the desired products.

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14

USIFOH, C. O. "3-Propynyl-2-substituted Carboxylic Acid Derivatives of Quinazolinone." Scientia Pharmaceutica 68, no. 3 (2000): 275–79. http://dx.doi.org/10.3797/scipharm.aut-00-25.

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Alkylation of quinazolinone-2-carboxylic acids with propargyl bromide in dimethylformamide in the presence of potassium carbonate afforded 3-prop-2-ynyl quinazolinone-2-substituted carboxylic acid derivatives. Further reaction of 4b-c produced 5b-c, which indicates that N-alkylation occurs before esterification with a propynyl moiety.

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15

Wang, Huiqiao, and Kun Xu. "Cobalta-Electrocatalyzed Allylic C—H Alkylation." Chinese Journal of Organic Chemistry 42, no. 4 (2022): 1260. http://dx.doi.org/10.6023/cjoc202200021.

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16

Poss, A. J., and R. K. Belter. "The C-Alkylation of Ascorbic Acid." Synthetic Communications 18, no. 4 (1988): 417–23. http://dx.doi.org/10.1080/00397918808064004.

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17

Takrouri, Khuloud, Jehoshua Katzhendler, and Morris Srebnik. "C-Lithiation/Alkylation of Trimethylamine Cyanoborane." Organometallics 23, no. 11 (2004): 2817–20. http://dx.doi.org/10.1021/om049816p.

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18

Laurent, Gilbert. "5618982 Catalytic C-alkylation of ketones." Journal of Molecular Catalysis A: Chemical 125, no. 2-3 (1997): 181. http://dx.doi.org/10.1016/s1381-1169(98)80113-1.

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19

Young, Andrew J., and M. Christina White. "Catalytic Intermolecular Allylic CH Alkylation." Journal of the American Chemical Society 130, no. 43 (2008): 14090–91. http://dx.doi.org/10.1021/ja806867p.

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20

Seebach, Dieter, and Robert Haner. "C-Alkylation of Phenyithio Aziridine Carboxylates." Chemistry Letters 16, no. 1 (1987): 49–52. http://dx.doi.org/10.1246/cl.1987.49.

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21

Osipov, Sergey, and Daria Vorobyeva. "Selective Synthesis of 2- and 7-Substituted Indole Derivatives via Chelation-Assisted Metallocarbenoid C–H Bond Functionalization." Synthesis 50, no. 02 (2017): 227–40. http://dx.doi.org/10.1055/s-0036-1591498.

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Functionally substituted indole derivatives are important intermediates for the synthesis of new potential drug candidates exhibiting strong bioactivities. Over the past few years, significant progress has been made in the direct C–H functionalization of the indole ring through the usage of metal-catalyzed intermolecular cross-coupling with diazo compounds. Directing group strategy provides a unique possibility for selective insertion of carbenes catalytically generated from diazo compounds into challenging indole C2–H and C7–H bonds. This short review summarizes recent advances in carbenoid f

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22

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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23

Liu, Yang, Julie Oble та Giovanni Poli. "Switchable selectivity in Pd-catalyzed [3 + 2] annulations of γ-oxy-2-cycloalkenones with 3-oxoglutarates: C–C/C–C vs C–C/O–C bond formation". Beilstein Journal of Organic Chemistry 15 (16 травня 2019): 1107–15. http://dx.doi.org/10.3762/bjoc.15.107.

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Two complementary [3 + 2] annulation protocols between 3-oxoglutarates and cyclic γ-oxy-2-cycloalkenones, simply differing on the reaction temperature, are disclosed. These domino transformations allow C–C/O–C or C–C/C–C [3 + 2] annulations at will, via an intermolecular Pd-catalyzed C-allylation/intramolecular O- or C-1,4-addition sequence, respectively. In particular, exploiting the reversibility of the O-1,4-addition step, in combination with the irreversible C-1,4-addition/decarboxylation path, the intramolecular conjugate addition step could be diverted from the kinetic (O-alkylation) to

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24

Wang, Shucheng, Xuhu Huang, Zemei Ge, Xin Wang, and Runtao Li. "Metal-free C-3 alkylation of imidazopyridines with xanthates and convenient access to alpidem and zolpidem." RSC Advances 6, no. 68 (2016): 63532–35. http://dx.doi.org/10.1039/c6ra09046j.

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A metal-free process for the C-3 alkylation of imidazopyridines have been developed. Various alkylation products including alkyl ester-, cyano-, ketone- and amide-substituted imidazopyridines were prepared in good yields.

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25

Babu, Srinivasarao Arulananda, and Arup Dalal. "Pd(II)-Catalyzed Directing-Group-Aided C–H Arylation and Alkylation of Pyrene Core: Synthesis of C1,C2- and C1,C10-Disubstituted Pyrene Motifs." Synthesis 53, no. 18 (2021): 3307–24. http://dx.doi.org/10.1055/a-1472-0881.

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AbstractWe report the application of the Pd(II)-catalyzed, directing-group-aided C–H arylation/alkylation tactics to functionalize the pyrene core, especially, the relatively inaccessible C2 and K-region C10 positions of the pyrene core and augmentation of the library of pyrene derivatives with C1,C2- and C1,C10-disubstituted pyrene motifs. The Pd(II)-catalyzed β-C–H arylation/alkylation of the C2-position of pyrene-1-carboxamide possessing an 8-aminoquinoline directing group yielded various C1,C2-disubstituted pyrenes. Similarly, the Pd(II)-catalyzed selective γ-C–H arylation/alkylation of th

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26

Wang, Cui-Tian, Ming Li, Ya-Nan Ding, et al. "Alkylation-Terminated Catellani Reactions by Cyclobutanol C–C Cleavage." Organic Letters 23, no. 3 (2021): 786–91. http://dx.doi.org/10.1021/acs.orglett.0c04018.

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27

Wang, Hong-Yi, You-Cheng Liu, and Qing-Xiang Guo. "Cyclizations of 2-(o-bromomethyl)benzylidene-1, 3-indandione initiated by 1-benzyl-1, 4-dihydronicotinamide and KCN: Selectivity of O-alkylation and C-alkylation." Journal of Chemical Research 2000, no. 2 (2000): 82–83. http://dx.doi.org/10.3184/030823400103166454.

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1-Benzyl-1, 4-dihydronicotinamide (1) and KCN reacted with 2-( o-bromomethyl)-benzylidene-1, 3-indandione (2) to give 7, 12-dihydro-1-oxoindeno[3, 2-c][2]benzooxepine (3) and 1′-cyano-3′-hydro-2, 2′-spirobi[2H-indene]-1, 3-dione (4), respectively, and the selectivity of O-alkylation and C-alkylation is discussed.

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28

Zhu, Xiang Xue, Fu Cun Chen, Jie An, Peng Zeng, and Long Ya Xu. "Development and Industrialization of the Ethylbenzene Production Technologies from Dilute Ethylene in FCC Dry Gas." Advanced Materials Research 233-235 (May 2011): 1708–13. http://dx.doi.org/10.4028/www.scientific.net/amr.233-235.1708.

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This article demonstrates the design and industrial operation results of the ethylbenzene(EB) production technology from FCC dry gas by a combination of gas-phase alkylation and liquid-phase transalkylation, developed and commercialized by Dalian Institute of Chemical Physics (DICP), CAS. Based on the high active modified ZSM-5/ZSM-11 co-crystalline zeolite alkylation catalyst and modified β zeolite transalkylation catalyst, both the alkylation and transalkylation reactions are performed under much milder conditions, resulting in low energy cost and low content of xylenes impurities in the EB

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29

Oregui-Bengoechea, Mikel, Inaki Gandarias, Pedro L. Arias, and Tanja Barth. "Solvent and catalyst effect in the formic acid aided lignin-to-liquids." Bioresoruce Technology 270 (September 13, 2018): 529–36. https://doi.org/10.1016/j.biortech.2018.09.062.

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The effect of the type of solvent, ethanol or water, and a Ru/C catalyst were studied in the formic acid aided lignin conversion. The best results were obtained in the presence of the Ru/C catalyst and using ethanol as solvent at 300 °C and 10 h (i.e. 75.8 wt% of oil and 23.9 wt% of solids). In comparison to the water system, the ethanol system yields a significantly larger amount of oil and, at 300 °C and 10 h, a smaller amount of solids. The main reasons for this positive effect of the ethanol solvent are i) the formation of ethanol-derived esters, ii) C-alkylations of lignin fragmen

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30

Oregui-Bengoechea, Mikel, Inaki Gandarias, Pedro L. Arias, and Tanja Barth. "Solvent and catalyst effect in the formic acid aided lignin-to-liquids." Bioresoruce Technology 270 (December 5, 2018): 529–39. https://doi.org/10.5281/zenodo.10606645.

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The effect of the type of solvent, ethanol or water, and a Ru/C catalyst were studied in the formic acid aided lignin conversion. The best results were obtained in the presence of the Ru/C catalyst and using ethanol as solvent at 300 °C and 10 h (i.e. 75.8 wt% of oil and 23.9 wt% of solids). In comparison to the water system, the ethanol system yields a significantly larger amount of oil and, at 300 °C and 10 h, a smaller amount of solids. The main reasons for this positive effect of the ethanol solvent are i) the formation of ethanol-derived esters, ii) C-alkylations of lignin fragmen

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31

Dang, Tuan Thanh, Siah Pei Shan, Balamurugan Ramalingam та Abdul Majeed Seayad. "An efficient heterogenized palladium catalyst for N-alkylation of amines and α-alkylation of ketones using alcohols". RSC Advances 5, № 53 (2015): 42399–406. http://dx.doi.org/10.1039/c5ra07225e.

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Silica supported palladium–NiXantphos complex is an efficient and high turnover heterogeneous catalyst for N-alkylation of amines and α-alkylation of ketones using alcohols under neat conditions at 120–140 °C following hydrogen borrowing strategy.

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32

Bégué, Jean-Pierre, Micheline Charpentier-Morize, and Gérard Née. "Alkylation of ethyl 4,4,4-trifluoroacetoacetate. First example of a reversible O-alkylation process leading to C-alkylation." J. Chem. Soc., Chem. Commun., no. 2 (1989): 83–84. http://dx.doi.org/10.1039/c39890000083.

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33

Darvesh, Sultan, Andrew S. Grant, David I. MaGee, and Zdenek Valenta. "Synthetic studies towards bruceantin. Part 1. Establishment of the carbon network." Canadian Journal of Chemistry 69, no. 4 (1991): 712–22. http://dx.doi.org/10.1139/v91-902.

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In a synthetic approach to the biologically active quassinoid bruceantin 1, intermediate 47 was prepared, which contains all required C-atoms, rings A and B, and four of the 10 chiral centers of bruceantin. The possibilities for a convergent strategy were explored, in which a 5-carbon unit would be joined to a 15-carbon unit by three bonds. After the study of various alkylations and Michael additions needed for the key step, it was found that 3-iodo-1-trimethylsilyl-5-hexenyne44adds to the dianion of methyl ketone nitriles 3 and 13 cheme-, diastereo-, and enantioselectively.Key words: bruceant

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34

Li, Hui, and Chao-Guo Yan. "The unprecedented C-alkylation and tandem C-/O-alkylation of phenanthrolinium salts with cyclic 1,3-dicarbonyl compounds." Tetrahedron 67, no. 16 (2011): 2863–69. http://dx.doi.org/10.1016/j.tet.2011.02.063.

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35

Stefanova, Maya D., and Ivo Lang. "Fractionation of soluble portion of reductively alkylated bituminous coals." Collection of Czechoslovak Chemical Communications 51, no. 5 (1986): 1071–82. http://dx.doi.org/10.1135/cccc19861071.

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Five bituminous coals were reductively alkylated with potassium and 1-butyl iodide in THF. The benzene soluble portion of reductively butylated coals were separated into the saturates, aromatics, neutral heterocyclics, ethers and polar compounds on a silica gel column. From the saturates, the n-alkanes were isolated by the thin-layer and column chromatography on silica gel, and then analyzed by GC. The aromatics were fractionated on a dual packed SiO2/Al2O3 column. The mono- and diaromatic fractions obtained were studied by GC-MS method. The non-hydrocarbon and polar compounds were charcterize

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36

Qian, Bo, Hongli Bao, Yuehua Zeng, and Yajun Li. "A Metal-Free Approach for Brønsted Acid Promoted C–H Alkylation of Heteroarenes with Alkyl Peroxides." Synthesis 50, no. 16 (2018): 3250–56. http://dx.doi.org/10.1055/s-0037-1609965.

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A metal-free protocol for Minisci C–H alkylation of heteroarenes using alkyl peroxides as the alkylating reagents and internal oxidants simultaneously under promotion of Brønsted acid has been demonstrated. A series of alkyl substituted heteroarenes were readily prepared by the C–H alkylation in moderate to good yields. A possible pathway involving the addition of alkyl radical to heterocycle followed by rearomatization is described.

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37

Wang, Mingan, Zhao Yu, Liu Xinlei, Wang Weiwei, and Geng Rui. "Cs2CO3-Promoted C-3 Alkylation of 4-[(2,2-Difluoroethyl)amino]-5,5-disubstituted Furan-2(5H)-ones with Heteroarylmethyl Chlorides." Synthesis 50, no. 20 (2018): 4055–62. http://dx.doi.org/10.1055/s-0037-1609548.

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4-(2,2-Difluoroethylamino)-3-(heteroarylmethyl)-5,5-disubstituted furan-2(5H)-ones were regioselectively synthesized via C-3 alkylation of 4-(2,2-difluoroethylamino)-5,5-disubstituted furan-2(5H)-ones with heteroarylmethyl chlorides using Cs2CO3 as a base in 62–85% yields. Their structures were characterized by 1H and 13C NMR, HRMS (ESI), and X-ray diffraction. This C-alkylation selectivity was rationalized by bulky hindrance and electron-withdrawing effects.

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38

Pulagam, Madhuri, and Hari Babu Bollikolla. "PEG 400-Catalyzed C3 & O-Alkylation Reactions of 4-Hydroxycoumarin-A Study." Current Chemistry Letters 14, no. 1 (2025): 129–38. http://dx.doi.org/10.5267/j.ccl.2024.8.004.

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PEG-400 has been found to be an efficient recyclable catalyst/solvent system for C3- and O-alkylation of 4-hydroxycoumarin with various electronically and structurally divergent alcohols with moderate to good yield of products. For the C3-alkylation using styrenes required Zn(OAc)2.2H2O (5 mol%) in PEG-400 at 70 °C. For the O-alkylation of 4-hydroxycoumarin with acetates required PEG-400 at 60 °C. This process offered a gentle and uncomplicated way to obtain multi-substituted pyranocoumarins, as well. This protocol's benefits include its wide use, moderate environment, low cost, reusable catal

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39

Sun, Fenggang, Miao Li, and Zhenhua Gu. "Pd/norbornene-catalyzed sequential ortho-C–H alkylation and ipso-alkynylation: a 1,1-dimethyl-2-alkynol strategy." Organic Chemistry Frontiers 3, no. 3 (2016): 309–13. http://dx.doi.org/10.1039/c5qo00391a.

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A palladium/norbornene-catalyzedortho-C–H alkylation andipso-alkynylation reaction for the synthesis of 2-alkyl-1-alkynyl arenes was reported, where the use of bulky 1,1-dimethyl-2-alkynols led to significant suppression of the formation ofO-alkylation and norbornene alkynylation by-products.

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40

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 (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

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41

Gelmont, Mark, Michael Yuzefovitch, David Yoffe, Eyal Eden, and Sergei Levchik. "Alkylation of Aromatic Compounds with Pentabromobenzyl Bromide and Tetrabromoxylene Dibromide as a New Route to High Molecular Weight Brominated Flame Retardants." Polymers 12, no. 2 (2020): 352. http://dx.doi.org/10.3390/polym12020352.

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In the view of many national and international human health and environmental regulations, polymeric flame retardants are sustainable products. In this work, a series of high molecular weight and polymeric brominated flame retardants are synthesized by the alkylation of aromatic molecules or the alkylation of aromatic polymers with pentabromobenzyl bromide (PBBB) or tetrabromoxylylene dibromide (TBXDB). The flame retardants prepared via the alkylation of toluene or diphenylethane with PBBB were found to be not truly polymeric but had high Mw > 1400. However, the alkylation of the same aroma

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42

Ashokan, D., and K. Rajathi. "Synthesis, Structural Identification and Biological Potencies of Quinolinium Sulfonamide Ionic Liquids." International Journal of Pharmaceutical Sciences and Drug Research 15, no. 03 (2023): 342–49. http://dx.doi.org/10.25004/ijpsdr.2023.150315.

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Members of the quinoline family include several alkaloids. Alkaloids are found in foods and beverages that humans consume daily and in various stimulants. Among many other activities, they act against inflammation, cancer, bacteria, fungi and pain. Modifications of the alkyl chain after N-alkylation can alter the physicochemical properties and affect its multifunctional properties. This article describes the preparation and structural identification of five quinolinium sulfonamide ionic liquids that differ in N-alkylation functional group and chain length. Functional group and alkyl chain leng

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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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44

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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Pan, S. S., T. Iracki, and N. R. Bachur. "DNA alkylation by enzyme-activated mitomycin C." Molecular Pharmacology 29, no. 6 (1986): 622–28. https://doi.org/10.1016/s0026-895x(25)10292-7.

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Glorius, F., M. Padmanaban, and A. Biju. "NHC-Catalyzed C-H Alkylation of Aldehydes." Synfacts 2011, no. 02 (2011): 0209. http://dx.doi.org/10.1055/s-0030-1259358.

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Trost, Barry M., and F. Dean Toste. "Asymmetric O- and C-Alkylation of Phenols." Journal of the American Chemical Society 120, no. 4 (1998): 815–16. http://dx.doi.org/10.1021/ja972453i.

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Krawczyk, Henryk, and Ryszard Bodalski. "C-Alkylation of hydroxyarenes by Michael reaction." Journal of the Chemical Society, Perkin Transactions 1, no. 13 (2001): 1559–65. http://dx.doi.org/10.1039/b101210j.

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Zelenin, A. E., N. D. Chkanikov, M. V. Galakhov, A. F. Kolomiets, and A. V. Fokin. "C-alkylation of N-alkylanilines by polyfluoroketones." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 4 (1985): 850–53. http://dx.doi.org/10.1007/bf00948075.

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Babu, Kaki Raveendra, Nengbo Zhu, and Hongli Bao. "Iron-Catalyzed C–H Alkylation of Heterocyclic C–H Bonds." Organic Letters 19, no. 1 (2016): 46–49. http://dx.doi.org/10.1021/acs.orglett.6b03287.

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