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Journal articles on the topic 'Alkyl-Aryl couplings'

Author: Grafiati

Published: 14 December 2024

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1

Bisz, Elwira, and Michal Szostak. "Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling of Aryl Chlorobenzoates with Alkyl Grignard Reagents." Molecules 25, no. 1 (January 6, 2020): 230. http://dx.doi.org/10.3390/molecules25010230.

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Aryl benzoates are compounds of high importance in organic synthesis. Herein, we report the iron-catalyzed C(sp2)–C(sp3) Kumada cross-coupling of aryl chlorobenzoates with alkyl Grignard reagents. The method is characterized by the use of environmentally benign and sustainable iron salts for cross-coupling in the catalytic system, employing benign urea ligands in the place of reprotoxic NMP (NMP = N-methyl-2-pyrrolidone). It is notable that high selectivity for the cross-coupling is achieved in the presence of hydrolytically-labile and prone to nucleophilic addition phenolic ester C(acyl)–O bonds. The reaction provides access to alkyl-functionalized aryl benzoates. The examination of various O-coordinating ligands demonstrates the high activity of urea ligands in promoting the cross-coupling versus nucleophilic addition to the ester C(acyl)–O bond. The method showcases the functional group tolerance of iron-catalyzed Kumada cross-couplings.

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2

Xu, Meng-Yu, and Bin Xiao. "Germatranes and carbagermatranes: (hetero)aryl and alkyl coupling partners in Pd-catalyzed cross-coupling reactions." Chemical Communications 57, no. 89 (2021): 11764–75. http://dx.doi.org/10.1039/d1cc04373k.

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3

Bernauer, Josef, Guojiao Wu, and Axel Jacobi von Wangelin. "Iron-catalysed allylation–hydrogenation sequences as masked alkyl–alkyl cross-couplings." RSC Advances 9, no. 54 (2019): 31217–23. http://dx.doi.org/10.1039/c9ra07604b.

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An iron-catalysed allylation of organomagnesium reagents (alkyl, aryl) with simple allyl acetates proceeds under mild conditions (Fe(OAc)₂ or Fe(acac)₂, Et₂O, r.t.) to furnish various alkene and styrene derivatives.

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4

Crisp, GT, and S. Papadopoulos. "Palladium-Mediated Transformations of Heteroaromatic Triflates." Australian Journal of Chemistry 42, no. 2 (1989): 279. http://dx.doi.org/10.1071/ch9890279.

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Quinolyl triflates and isoquinolyl triflates undergo palladium-catalysed couplings with organostannanes, organoaluminiums and activated alkenes. The range of organic groups which can be transferred to the heteroaromatic substrate includes aryl, vinyl, alkynyl, alkyl and hydride.

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5

Cauley, Anthony N., Melda Sezen-Edmonds, Eric M. Simmons, and Cullen L. Cavallaro. "Increasing saturation: development of broadly applicable photocatalytic Csp2–Csp3 cross-couplings of alkyl trifluoroborates and (hetero)aryl bromides for array synthesis." Reaction Chemistry & Engineering 6, no. 9 (2021): 1666–76. http://dx.doi.org/10.1039/d1re00192b.

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HTE was used to systematically investigate the reaction of alkyl trifluoroborates and aryl bromides under photocatalytic conditions. General conditions were identified for coupling of activated primary, benzylic and secondary alkyl trifluoroborates.

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6

Davis, Mia, Mathias O. Senge, and Oliver B. Locos. "Anthracenylporphyrins." Zeitschrift für Naturforschung B 65, no. 12 (December 1, 2010): 1472–84. http://dx.doi.org/10.1515/znb-2010-1211.

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We report the synthesis and characterization of meso-anthracenylporphyrins with zinc and nickel metal centers. A variety of novel aryl and alkyl meso-substituted anthracenylporphyrins were synthesized via step-wise Suzuki cross-coupling reactions using anthracenyl boronates. This method was compared to standard syntheses based on condensation reactions to yield anthracenylporphyrins of the A2B2- and A3B-type. The work was complemented by the synthesis of a number of the functionalized anthracene derivatives via Suzuki couplings. Selected systems were subjected to single-crystal X-ray analysis which revealed an unusual close packing for nickel(II) anthracenylporphyrins.

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7

Parmar, Dixit, Lena Henkel, Josef Dib, and Magnus Rueping. "Iron catalysed cross-couplings of azetidines – application to the formal synthesis of a pharmacologically active molecule." Chemical Communications 51, no. 11 (2015): 2111–13. http://dx.doi.org/10.1039/c4cc09337b.

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A protocol for the cross-coupling of azetidines with aryl, heteroaryl, vinyl and alkyl Grignard reagents has been developed under iron catalysis. In addition, a short formal synthesis of a pharmacologically active molecule was demonstrated.

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8

Paul, Avishek, Mark D. Smith, and Aaron K. Vannucci. "Photoredox-Assisted Reductive Cross-Coupling: Mechanistic Insight into Catalytic Aryl–Alkyl Cross-Couplings." Journal of Organic Chemistry 82, no. 4 (February 2, 2017): 1996–2003. http://dx.doi.org/10.1021/acs.joc.6b02830.

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9

Villanueva-Kasis, Oscar, Denisse A. de Loera, Sandra L. Castañón-Alonso, Armando Domínguez-Ortiz, Leticia Lomas-Romero, Ilich A. Ibarra, Eduardo González-Zamora, and Alejandro Islas-Jácome. "Efficient Synthesis of New α-β-Unsaturated Alkyl-Ester Peptide-Linked Chiral Amines." Proceedings 9, no. 1 (November 14, 2018): 34. http://dx.doi.org/10.3390/ecsoc-22-05769.

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Four new α-β-unsaturated alkyl-ester chiral amines were synthesized in excellent yields (77–95%) via peptide couplings from their corresponding α-β-unsaturated alkyl-ester anilines and N-Boc protected chiral aminoacids. To our delight, these polyfunctionalized compounds are being used as starting reagents in Ugi-type three-component reactions (Ugi-3CR) together with alkyl- and aryl-aldehydes and a chain-ring tautomerizable amino acid-containing isocyanide to synthesize novel oxazole-based macrocycle precursors. Thus, the aim of this communication is to show our most recent results of the synthesis and use of new and complex chiral amines to assemble macrocyclic polypeptides with potential application in medicinal chemistry, such as the post-surgical antibiotic Vancomycin.

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10

Sedláček, Ondřej, Petra Břehová, Radek Pohl, Antonín Holý, and Zlatko Janeba. "The synthesis of the 8-C-substituted 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP) derivatives by diverse cross-coupling reactions." Canadian Journal of Chemistry 89, no. 4 (April 2011): 488–98. http://dx.doi.org/10.1139/v11-001.

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Diisopropyl 8-bromo-2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine was used as a starting material for the synthesis of the 8-C-substituted 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP) analogues. A systematic screening of diverse cross-coupling reactions was carried out. Stille, Suzuki–Miyaura, Negishi, and Sonogashira cross-couplings, as well as Pd-catalysed reactions with trialkylaluminiums, were employed for the introduction of various alkyl, alkenyl, alkynyl, aryl, and hetaryl substituents to the C-8 position of the 2,6-diaminopurine moiety. In contrast to the potent parent compound PMEDAP, which exhibits potent antiretroviral and antitumor activity, none of the sixteen newly synthesized 8-C-substituted analogues of PMEDAP showed any specific antiviral activity.

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11

Cornella, Josep, and Matthew O’Neill. "Retaining Alkyl Nucleophile Regiofidelity in Transition-Metal-Mediated Cross-Couplings to Aryl Electrophiles." Synthesis 50, no. 20 (September 10, 2018): 3974–96. http://dx.doi.org/10.1055/s-0037-1609941.

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While the advent of transition-metal catalysis has undoubtedly transformed synthetic chemistry, problems persist with the introduction of secondary and tertiary alkyl nucleophiles into C(sp2) aryl electrophiles. Complications arise from the delicate organometallic intermediates typically invoked by such processes, from which competition between the desired reductive elimination event and the deleterious β-H elimination pathways can lead to undesired isomerization of the incoming nucleophile. Several methods have integrated distinct combinations of metal, ligand, nucleophile, and electrophile to provide solutions to this problem. Despite substantial progress, refinements to current protocols will facilitate the realization of complement reactivity and improved functional group tolerance. These issues have become more pronounced in the context of green chemistry and sustainable catalysis, as well as by the current necessity to develop robust, reliable cross-couplings beyond less explored C(sp2)–C(sp2) constructs. Indeed, the methods discussed herein and the elaborations thereof enable an ‘unlocking’ of accessible topologically enriched chemical space, which is envisioned to influence various domains of application.1 Introduction2 Mechanistic Considerations3 Magnesium Nucleophiles4 Zinc Nucleophiles5 Boron Nucleophiles6 Other Nucleophiles7 Tertiary Nucleophiles8 Reductive Cross-Coupling with in situ Organometallic Formation9 Conclusion

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12

Liu, Lei, Maria Camila Aguilera, Wes Lee, Cassandra R. Youshaw, Michael L. Neidig, and Osvaldo Gutierrez. "General method for iron-catalyzed multicomponent radical cascades–cross-couplings." Science 374, no. 6566 (October 22, 2021): 432–39. http://dx.doi.org/10.1126/science.abj6005.

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Iron links a trio Iron holds particular appeal as a catalytic metal—it is safe and abundant, as well as a mainstay of enzymatic reactivity. Nonetheless, in synthetic construction of carbon-carbon bonds, modern chemists have largely had to rely on rarer metals such as palladium. Liu et al . now report that coordination of iron by a bulky chelating phosphine ligand enables efficient mutual coupling of three different reactants—an alkyl halide, an aryl Grignard, and an olefin—to form two carbon-carbon bonds (see the Perspective by Lefèvre). A combination of Mössbauer spectroscopy, crystallography, and computational simulations illuminates the mechanism. —JSY

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13

Perkins, Robert J., Alexander J. Hughes, Daniel J. Weix, and Eric C. Hansen. "Metal-Reductant-Free Electrochemical Nickel-Catalyzed Couplings of Aryl and Alkyl Bromides in Acetonitrile." Organic Process Research & Development 23, no. 8 (July 22, 2019): 1746–51. http://dx.doi.org/10.1021/acs.oprd.9b00232.

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14

Pang, Haobo, Ye Wang, Fabrice Gallou, and Bruce H. Lipshutz. "Fe-Catalyzed Reductive Couplings of Terminal (Hetero)Aryl Alkenes and Alkyl Halides under Aqueous Micellar Conditions." Journal of the American Chemical Society 141, no. 43 (September 27, 2019): 17117–24. http://dx.doi.org/10.1021/jacs.9b04510.

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15

Alsabeh, Pamela G., and Mark Stradiotto. "Addressing Challenges in Palladium-Catalyzed Cross-Couplings of Aryl Mesylates: Monoarylation of Ketones and Primary Alkyl Amines." Angewandte Chemie 125, no. 28 (June 12, 2013): 7383–87. http://dx.doi.org/10.1002/ange.201303305.

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16

Alsabeh, Pamela G., and Mark Stradiotto. "Addressing Challenges in Palladium-Catalyzed Cross-Couplings of Aryl Mesylates: Monoarylation of Ketones and Primary Alkyl Amines." Angewandte Chemie International Edition 52, no. 28 (June 12, 2013): 7242–46. http://dx.doi.org/10.1002/anie.201303305.

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17

Shen, Zhi-Liang, Kelvin Kau Kiat Goh, Yong-Sheng Yang, Yin-Chang Lai, Colin Hong An Wong, Hao-Lun Cheong, and Teck-Peng Loh. "Direct Synthesis of Water-Tolerant Alkyl Indium Reagents and Their Application in Palladium-Catalyzed Couplings with Aryl Halides." Angewandte Chemie International Edition 50, no. 2 (December 5, 2010): 511–14. http://dx.doi.org/10.1002/anie.201005798.

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18

Shen, Zhi-Liang, Kelvin Kau Kiat Goh, Yong-Sheng Yang, Yin-Chang Lai, Colin Hong An Wong, Hao-Lun Cheong, and Teck-Peng Loh. "Direct Synthesis of Water-Tolerant Alkyl Indium Reagents and Their Application in Palladium-Catalyzed Couplings with Aryl Halides." Angewandte Chemie 123, no. 2 (December 5, 2010): 531–34. http://dx.doi.org/10.1002/ange.201005798.

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19

Alsabeh, Pamela G., and Mark Stradiotto. "ChemInform Abstract: Addressing Challenges in Palladium-Catalyzed Cross-Couplings of Aryl Mesylates: Monoarylation of Ketones and Primary Alkyl Amines." ChemInform 44, no. 48 (November 8, 2013): no. http://dx.doi.org/10.1002/chin.201348089.

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20

Shen, Zhi-Liang, Kelvin Kau Kiat Goh, Yong-Sheng Yang, Yin-Chang Lai, Colin Hong An Wong, Hao-Lun Cheong, and Teck-Peng Loh. "ChemInform Abstract: Direct Synthesis of Water-Tolerant Alkyl Indium Reagents and Their Application in Palladium-Catalyzed Couplings with Aryl Halides." ChemInform 42, no. 20 (April 21, 2011): no. http://dx.doi.org/10.1002/chin.201120040.

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21

Li, Zhuang, Bing Lu, Hongmei Sun, Qi Shen, and Yong Zhang. "Ionic iron(III) complexes bearing a dialkylbenzimidazolium cation: Efficient catalysts for magnesium-mediated cross-couplings of aryl phosphates with alkyl bromides." Applied Organometallic Chemistry 31, no. 8 (December 12, 2016): e3671. http://dx.doi.org/10.1002/aoc.3671.

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22

Ma, Dawei, and Jiqing Jiang. "Pd/Cu-catalyzed couplings of β-amino esters with aryl bromides. Synthesis of chiral 1,2,3,4-tetrahydro-4-oxo-2-alkyl-1-quinolines." Tetrahedron: Asymmetry 9, no. 7 (April 1998): 1137–42. http://dx.doi.org/10.1016/s0957-4166(98)00078-0.

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23

MA, D., and J. JIANG. "ChemInform Abstract: Pd/Cu-Catalyzed Couplings of β-Amino Esters with Aryl Bromides. Synthesis of Chiral 1,2,3,4-Tetrahydro-4-oxo-2-alkyl-1-quinolines." ChemInform 29, no. 34 (June 20, 2010): no. http://dx.doi.org/10.1002/chin.199834171.

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24

Yuan, Mingbin, Zhihui Song, Shorouk O. Badir, Gary A. Molander, and Osvaldo Gutierrez. "On the Nature of C(sp3)–C(sp2) Bond Formation in Nickel-Catalyzed Tertiary Radical Cross-Couplings: A Case Study of Ni/Photoredox Catalytic Cross-Coupling of Alkyl Radicals and Aryl Halides." Journal of the American Chemical Society 142, no. 15 (March 20, 2020): 7225–34. http://dx.doi.org/10.1021/jacs.0c02355.

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25

Yuan, Jiwen, Chao Liu, and Aiwen Lei. "Oxidative cross S–H/S–H coupling: selective synthesis of unsymmetrical aryl tert-alkyl disulfanes." Organic Chemistry Frontiers 2, no. 6 (2015): 677–80. http://dx.doi.org/10.1039/c5qo00027k.

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Selective oxidative coupling between equivalent aryl and tert-alkyl mercaptans was achieved under mild condition. This protocol may provide an efficient process to synthesize the unsymmetrical aryl tert-alkyl disulfides.

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26

Jia, Xiao, Xinghua Zhang, Qun Qian, and Hegui Gong. "Alkyl–aryl ketone synthesis via nickel-catalyzed reductive coupling of alkyl halides with aryl acids and anhydrides." Chemical Communications 51, no. 51 (2015): 10302–5. http://dx.doi.org/10.1039/c5cc03113c.

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27

Dey, Supriya, and Narayanaswamy Jayaraman. "Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine." Beilstein Journal of Organic Chemistry 8 (April 10, 2012): 522–27. http://dx.doi.org/10.3762/bjoc.8.59.

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This paper deals with the synthesis of 2-deoxy-2-C-alkyl/aryl septanosides. A range of such septanoside derivatives was synthesized by using a common bromo-oxepine intermediate, involving C–C bond forming organometallic reactions. Unsaturated, seven-membered septanoside vinyl bromides or bromo-oxepines, obtained through a ring expansion methodology of the cyclopropane derivatives of oxyglycals, displayed a good reactivity towards several acceptor moieties in C–C bond forming Heck, Suzuki and Sonogashira coupling reactions, thus affording 2-deoxy-2-C-alkyl/aryl septanosides. Whereas Heck and Sonogashira coupling reactions afforded 2-deoxy-2-C-alkenyl and -alkynyl derivatives, respectively, the Suzuki reaction afforded 2-deoxy-2-C-aryl septanosides. Deprotection and reduction of the 2-deoxy-2-alkenyl derivative afforded the corresponding 2-deoxy-2-C-alkyl septanoside free of protecting groups. The present study illustrates the reactivity of bromo-oxepine in the synthesis of hitherto unknown septanosides, branching out at C-2, through C–C bond formation with alkyl and aryl substituents.

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28

Sakai, Norio, Hiromu Maeda, and Yohei Ogiwara. "Copper-Catalyzed Three-Component Coupling Reaction of Aryl Iodides, a Disilathiane, and Alkyl Benzoates Leading to a One-Pot Synthesis of Alkyl Aryl Sulfides." Synthesis 51, no. 11 (March 18, 2019): 2323–30. http://dx.doi.org/10.1055/s-0037-1610869.

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A copper-catalyzed three-component coupling reaction of aryl iodides, hexamethyldisilathiane and alkyl benzoates leading to alkyl aryl sulfides has been demonstrated. A disilathiane acted as both a sulfur source and a promoter of the sulfidation, and the alkyl moiety of the alkyl benzoate was effectively introduced on one side of the sulfide. Moreover, we found that the protocol can be expanded to the preparation of ethyl phenyl selenide with diphenyl diselenide.

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29

Kumaraswamy, Gullapalli, Ragam Raju, and Vykunthapu Narayanarao. "Metal- and base-free syntheses of aryl/alkylthioindoles by the iodine-induced reductive coupling of aryl/alkyl sulfonyl chlorides with indoles." RSC Advances 5, no. 29 (2015): 22718–23. http://dx.doi.org/10.1039/c5ra00646e.

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30

Li, Chengxi, Guolan Xiao, Qing Zhao, Huimin Liu, Tao Wang, and Wenjun Tang. "Sterically demanding aryl–alkyl Suzuki–Miyaura coupling." Org. Chem. Front. 1, no. 3 (2014): 225–29. http://dx.doi.org/10.1039/c4qo00024b.

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31

Bisz, Elwira. "Iron-Catalyzed Cross-Coupling Reactions of Alkyl Grignards with Aryl Chlorobenzenesulfonates." Molecules 26, no. 19 (September 29, 2021): 5895. http://dx.doi.org/10.3390/molecules26195895.

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Aryl sulfonate esters are versatile synthetic intermediates in organic chemistry as well as attractive architectures due to their bioactive properties. Herein, we report the synthesis of alkyl-substituted benzenesulfonate esters by iron-catalyzed C(sp2)–C(sp3) cross-coupling of Grignard reagents with aryl chlorides. The method operates using an environmentally benign and sustainable iron catalytic system, employing benign urea ligands. A broad range of chlorobenzenesulfonates as well as challenging alkyl organometallics containing β-hydrogens are compatible with these conditions, affording alkylated products in high to excellent yields. The study reveals that aryl sulfonate esters are the most reactive activating groups for iron-catalyzed alkylative C(sp2)–C(sp3) cross-coupling of aryl chlorides with Grignard reagents.

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32

Zhu, Dan, and Lei Shi. "Ni-Catalyzed cross-coupling of aryl thioethers with alkyl Grignard reagents via C–S bond cleavage." Chemical Communications 54, no. 67 (2018): 9313–16. http://dx.doi.org/10.1039/c8cc03665a.

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33

Atar, Amol Balu, Jongmin Kang, and Arvind H. Jadhav. "A [bmim]Cl-promoted domino protocol using an isocyanide-based [4+1]-cycloaddition reaction for the synthesis of diversely functionalized 3-alkylamino-2-alkyl/aryl/hetero-aryl indolizine-1-carbonitriles under solvent-free conditions." New Journal of Chemistry 44, no. 8 (2020): 3241–48. http://dx.doi.org/10.1039/c9nj05738b.

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A room temperature-based ionic liquid [bmim]Cl-catalyzed multicomponent coupling strategy for the synthesis of 3-alkylamino-2-alkyl/aryl/hetero-aryl indolizine-1-carbonitrile derivatives under mild conditions is shown.

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34

Sang, Dayong, Jiahui Wang, Yun Zheng, Jianyuan He, Caili Yuan, Qing An, and Juan Tian. "Carbodiimides as Acid Scavengers in Aluminum Triiodide Induced Cleavage of Alkyl Aryl Ethers." Synthesis 49, no. 12 (March 14, 2017): 2721–26. http://dx.doi.org/10.1055/s-0036-1588755.

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A practical procedure for the cleavage of alkyl aryl ethers containing labile functional groups has been developed using aluminum triiodide as the ether cleaving reagent. Carbodiimides, typically used as dehydration reagents for the coupling of amines and carboxylic acids to yield amide bonds, are found to be effective hydrogen iodide scavengers that prevent acid-labile groups from deterioration. The method is applicable to variant alkyl aryl ethers such as eugenol, vanillin, ortho-vanillin and methyl eugenol. Suitable substrates are not limited to alkyl o-hydroxyphenyl ethers.

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35

Zhu, Jiayi, Yu Chen, Feng Lin, Baoshuang Wang, Zhengwang Chen, and Liangxian Liu. "NiSO4-catalyzed C–H activation/C–S cross-coupling of 1,2,3-triazole N-oxides with thiols." Organic & Biomolecular Chemistry 13, no. 12 (2015): 3711–20. http://dx.doi.org/10.1039/c4ob02586e.

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An efficient nickel-catalyzed protocol for C–S cross-coupling through the direct functionalization of 2-aryl-1,2,3-triazole N-oxide C–H bonds with aryl or alkyl thiols, or diphenyl disulfide has been developed.

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36

Singh, Pratibha, Rekha Bai, Rakhee Choudhary, Mahesh C. Sharma, and Satpal Singh Badsara. "Regio- and stereoselective syntheses of allylic thioethers under metal free conditions." RSC Advances 7, no. 49 (2017): 30594–602. http://dx.doi.org/10.1039/c7ra04817c.

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A metal-free, regio and stereoselective synthesis of allylic thioethers using densely functionalized allyl iodides and aryl/alkyl disulfides as coupling partners, provided the resulting allyl aryl thioethers in 62–92% isolated yields is described.

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37

Wang, Dungai, Jinlong Zhao, Weigang Xu, Changwei Shao, Zheng Shi, Liang Li, and Xinghua Zhang. "Metal- and base-free reductive coupling reaction of P(O)–H with aryl/alkyl sulfonyl chlorides: a novel protocol for the construction of P–S–C bonds." Organic & Biomolecular Chemistry 15, no. 3 (2017): 545–49. http://dx.doi.org/10.1039/c6ob02364a.

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38

Li, Zhuang, Ling Liu, Hong-mei Sun, Qi Shen, and Yong Zhang. "Alkyl Grignard cross-coupling of aryl phosphates catalyzed by new, highly active ionic iron(ii) complexes containing a phosphine ligand and an imidazolium cation." Dalton Transactions 45, no. 44 (2016): 17739–47. http://dx.doi.org/10.1039/c6dt02995g.

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39

Lin, Yang, Mingzhong Cai, Zhiqiang Fang, and Hong Zhao. "MCM-41-immobilized 1,10-phenanthroline–copper(i) complex: a highly efficient and recyclable catalyst for the coupling of aryl iodides with aliphatic alcohols." RSC Advances 6, no. 88 (2016): 85186–93. http://dx.doi.org/10.1039/c6ra19825b.

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40

Wang, Junlei, Binbin Huang, Chao Yang, and Wujiong Xia. "Visible-light-mediated defluorinative cross-coupling of gem-difluoroalkenes with thiols." Chemical Communications 55, no. 74 (2019): 11103–6. http://dx.doi.org/10.1039/c9cc05293c.

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41

Mukai, Shoma, and Nathan Werner. "Synthesis and Palladium-Catalyzed Cross-Coupling of an Alkyl-Substituted Alkenylboronic Acid Pinacol Ester with Aryl Bromides." American Journal of Undergraduate Research 20, no. 1 (June 30, 2023): 37–46. http://dx.doi.org/10.33697/ajur.2023.078.

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The palladium-catalyzed cross-coupling reaction of alkyl-substituted alkenylboron reagents with aryl halides is a versatile method to introduce a hydrophobic hydrocarbon chain onto organic compounds of interest. The application of the cross-coupling reaction is enabled by synthetic methods for the preparation of alkenylboron reagents. The geometrically pure, alkyl-substituted alkenylboron reagent, (E)-octenylboronic acid pinacol ester, was prepared by 9-BBN-catalyzed hydroboration reaction of 1-octene with pinacolborane in refluxing 1 M THF solution. This reagent was then evaluated in palladium-catalyzed cross-coupling reactions with aryl bromides. The highest yield of the (E)-1-phenyloctene was obtained when SPhos was used as the ligand, K2CO3 was used as the base, and DMF was used as the reaction solvent. Other electron-rich, electron-poor, sterically hindered, and heteroaromatic substrates produced the corresponding (E)-1-phenyloctene derivatives in moderate to good yield. KEYWORDS: Organic synthesis; Aryl alkene synthesis; Palladium-catalyzed cross-coupling; Suzuki-Miyaura reaction; Stereocontrolled alkene preparation; Hydroboration; 9-Borobicyclo[3.3.1]nonane; Reaction optimization

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42

Roslin, Sara, and Luke R. Odell. "Palladium and visible-light mediated carbonylative Suzuki–Miyaura coupling of unactivated alkyl halides and aryl boronic acids." Chemical Communications 53, no. 51 (2017): 6895–98. http://dx.doi.org/10.1039/c7cc02763j.

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43

Reddy, P. Linga, R. Arundhathi, and Diwan S. Rawat. "Cu(0)@Al2O3/SiO2 NPs: an efficient reusable catalyst for the cross coupling reactions of aryl chlorides with amines and anilines." RSC Advances 5, no. 112 (2015): 92121–27. http://dx.doi.org/10.1039/c5ra19337k.

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The C–N cross coupling reaction of aryl chlorides with various alkyl/aryl amines catalyzed by copper nanoparticles impregnated on alumina/silica support (Cu(0)@Al₂O₃/SiO₂) was investigated and the catalyst showed excellent reactivity and efficacy.

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44

Wang, Xie, Peipei Xie, Renhua Qiu, Longzhi Zhu, Ting Liu, You Li, Takanori Iwasaki, 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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45

Carrasco, Desirée, Mónica H. Pérez-Temprano, Juan A. Casares, and Pablo Espinet. "Cross Alkyl–Aryl versus Homo Aryl–Aryl Coupling in Palladium-Catalyzed Coupling of Alkyl–Gold(I) and Aryl–Halide." Organometallics 33, no. 13 (June 24, 2014): 3540–45. http://dx.doi.org/10.1021/om500446x.

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46

Sumida, Yuto, Takamitsu Hosoya, and Tomoe Sumida. "Nickel-Catalyzed Reductive Cross-Coupling of Aryl Triflates and Nonaflates with Alkyl Iodides." Synthesis 49, no. 16 (June 28, 2017): 3590–601. http://dx.doi.org/10.1055/s-0036-1588464.

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Abstract:

A nickel-catalyzed cross-electrophile coupling of aryl triflates and nonaflates with alkyl iodides using manganese(0) as a reductant is described. The method is applicable to the reductive alkylation of various aryl sulfonates, including o-borylaryl triflate, which enabled efficient construction of diverse alkylated arenes under mild conditions.

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47

Wu, Sisi, Weijia Shi, and Gang Zou. "Mechanical metal activation for Ni-catalyzed, Mn-mediated cross-electrophile coupling between aryl and alkyl bromides." New Journal of Chemistry 45, no. 25 (2021): 11269–74. http://dx.doi.org/10.1039/d1nj01732b.

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48

Li, Wei-Ze, and Zhong-Xia Wang. "A nickel-catalyzed silylation reaction of alkyl aryl sulfoxides with silylzinc reagents." Organic & Biomolecular Chemistry 19, no. 23 (2021): 5082–86. http://dx.doi.org/10.1039/d1ob00840d.

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49

Lévêque, Christophe, Ludwig Chenneberg, Vincent Corcé, Jean-Philippe Goddard, Cyril Ollivier, and Louis Fensterbank. "Primary alkyl bis-catecholato silicates in dual photoredox/nickel catalysis: aryl- and heteroaryl-alkyl cross coupling reactions." Organic Chemistry Frontiers 3, no. 4 (2016): 462–65. http://dx.doi.org/10.1039/c6qo00014b.

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50

Song, Liu-Yi, Meng-Ke Chen, Jian Wang, and Jing-Hua Li. "A straightforward coupling of 4-sulfonylpyridines with Grignard reagents." Journal of Chemical Research 46, no. 3 (March 2022): 174751982211035. http://dx.doi.org/10.1177/17475198221103502.

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Abstract:

A straightforward synthesis of alkyl-sulfonylpyridines and aryl-sulfonylpyridines is developed by coupling of sulfonylpyridines with the Grignard reagents. The protocol proceeds through a catalyst- and oxidant-free coupling of sulfonylpyridines as substrates via a Chichibabin-type reaction mechanism.

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