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Journal articles on the topic 'Aryl halides'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

Baik, Woonphil, Wanqiang Luan, Hyun Joo Lee, Cheol Hun Yoon, Sangho Koo, and Byeong Hyo Kim. "Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ." Canadian Journal of Chemistry 83, no. 3 (2005): 213–19. http://dx.doi.org/10.1139/v05-026.

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Halodimethylsulfonium halide 1, which is readily formed in situ from hydrohaloic acid and DMSO, is a good nucleophilic halide. This activated nucleophilic halide rapidly converts aryldiazonium salt prepared in situ by the same hydrohaloic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohaloic acid in DMSO is required for the direct transformation of aromatic amines, which results in the production of aryl halides within 1 h. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic

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2

Bhat, Balkrishen, and A. P. Bhaduri. "Grignard Reaction of 2-Substituted-3-Cyanoquinolines." Zeitschrift für Naturforschung B 40, no. 7 (1985): 990–95. http://dx.doi.org/10.1515/znb-1985-0724.

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Abstract Grignard reactions of 2-morpholino and 2-methylthio-3-cyanoquinoline, 2-chloro-3-cyanoquinoline, 2-chloro-3-cyano-6-methoxyquinoline and 2-chloro-3-cyano-7-methylquinoline with alkyl or aryl magnesium halides have been studied. It was found that 2-morpholino and 2-methylthio- 3-cyanoquinolines gave 1,4-addition products followed by rapid aromatisation. 2-Chloro-3- cyanoquinoline with alkyl magnesium halides furnished 1,4-addition products but with aryl magnesium halides 1,4- and 1,2-addition products were obtained. The cyano group of 4-aryl-2-chloro- 3-cyano-1,4-dihydroquinolines was

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3

Kabalka, G. W., Z. Wu, and Y. Ju. "Use of organoboron halides in organic synthesis." Pure and Applied Chemistry 75, no. 9 (2003): 1231–37. http://dx.doi.org/10.1351/pac200375091231.

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Several new organic transformations have been achieved utilizing boron halide reagents. Aryl aldehydes are conveniently converted to gem-dichloromethylbenzenes using boron trichloride. Aryl aldehydes are alkylated by alkylboron chlorides in a Grignard-like fashion to generate the corresponding arylalkanols or alkylboron chlorides. Aryl aldehydes react with divinylboron halides (generated via the haloboration of alkynes) to produce 1,5-di-halo-1,4-dienes in excellent yields.

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4

Ying, Jun, Zhengjie Le, Zhi-Peng Bao, and Xiao-Feng Wu. "Palladium-catalyzed double carbonylation of propargyl amines and aryl halides to access 1-aroyl-3-aryl-1,5-dihydro-2H-pyrrol-2-ones." Organic Chemistry Frontiers 7, no. 8 (2020): 1006–10. http://dx.doi.org/10.1039/d0qo00007h.

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5

Brian, Ptoton Mnangat, and Peter Musau. "Synthesis, Reactivity and Stability of Aryl Halide Protecting Groups towards Di-Substituted Pyridines." Indonesian Journal of Chemistry 16, no. 1 (2018): 53. http://dx.doi.org/10.22146/ijc.21177.

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This paper reports the synthesis and reactivity of different Benzyl derivative protecting groups. The synthesis and stability of Benzyl halides, 4-methoxybenzyl halides, 3,5-dimethoxybenzyl halides, 3,4-dimethoxybenzyl halides, 3,4,5-trimethoxybenzyl halide protecting groups and their reactivity towards nitrogen atom of a di-substituted pyridine ring in formation of pyridinium salts is also reported.

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6

Nelson, David J., and Feliu Maseras. "Steric effects determine the mechanisms of reactions between bis(N-heterocyclic carbene)-nickel(0) complexes and aryl halides." Chemical Communications 54, no. 75 (2018): 10646–49. http://dx.doi.org/10.1039/c8cc06379f.

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7

Liu, Xiaosong, Yunfei Song, Wei Zhang, et al. "Correction: Tracking intramolecular energy redistribution dynamics in aryl halides: the effect of halide mass." RSC Advances 8, no. 55 (2018): 31303. http://dx.doi.org/10.1039/c8ra90073f.

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8

Quesnel, Jeffrey S., Alexander Fabrikant, and Bruce A. Arndtsen. "A flexible approach to Pd-catalyzed carbonylations via aroyl dimethylaminopyridinium salts." Chemical Science 7, no. 1 (2016): 295–300. http://dx.doi.org/10.1039/c5sc02949j.

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9

Larina, E. V., A. A. Kurokhtina, N. A. Lagoda, and A. F. Schmidt. "Distinguishing between Linear and Non-Linear (Cooperative) Substrate Activation Mechanisms in the Sonogashira Reaction under “Ligand-Free” and “Copper-Free” Conditions." Кинетика и катализ 64, no. 6 (2023): 737–48. http://dx.doi.org/10.31857/s0453881123060102.

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The results are presented on the comparative studies of the differential selectivity patterns in the Sonogashira reaction with a pair of competing aryl acetylenes in the “ligand-free” and “copper-free” conditions when varying the nature and concentration of aryl halides and base. The revealed sensitivity of the differential selectivity of competing aryl acetylenes to aryl halide nature unambiguously indicated that the substrates were activated through linear mechanism from kinetic view. An absence of any influence of the nature and concentration of the base on the differential selectivity of c

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10

Leadbeater, Nicholas E., and Riina K. Arvela. "Fast and Easy Halide Exchangein Aryl Halides." Synlett, no. 8 (2003): 1145–48. http://dx.doi.org/10.1055/s-2003-39887.

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11

Baranano, David, Grace Mann, and John F. Hartwig. "Nickel and Palladium-Catalyzed Cross-Couplings that Form Carbon-Heteroatom and Carbon-Element Bonds." Current Organic Chemistry 1, no. 3 (1997): 287–305. http://dx.doi.org/10.2174/1385272801666220124194647.

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The transition-metal catalyzed addition of heteroatom nucleophiles to aryl and vinyl halides is reviewed. This chemistry typically involves a nickel- or palladium-based catalyst containing phosphine ligands. In recently developed palladium-catalyzed chemistry, aryl halides react with amines in the presence of base to form arylamines. In similar chemistry catalyzed by both nickel and palladium, aryl and vinyl halides react with alkali metal or tin thiolates or selenides to form aryl and vinyl sulfides, while the reaction of different phosphorus compounds, such as phosphides, phosphonates, and

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12

Lan, Jihong, Rongxiang Chen, Fangfang Duo, Menghui Hu, and Xiaoyan Lu. "Visible-Light Photocatalytic Reduction of Aryl Halides as a Source of Aryl Radicals." Molecules 27, no. 17 (2022): 5364. http://dx.doi.org/10.3390/molecules27175364.

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Aryl- and heteroaryl units are present in a wide variety of natural products, pharmaceuticals, and functional materials. The method for reduction of aryl halides with ubiquitous distribution is highly sought after for late-stage construction of various aromatic compounds. The visible-light-driven reduction of aryl halides to aryl radicals by electron transfer provides an efficient, simple, and environmentally friendly method for the construction of aromatic compounds. This review summarizes the recent progress in the generation of aryl radicals by visible-light-driven reduction of aryl halides

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13

Fan, Guo Zhi, Zhen Xiao Duan, and Min Wang. "Suzuki Reaction Catalyzed by Pd(II) Anchored on Polymer in Supercritical Carbon Dioxide." Advanced Materials Research 466-467 (February 2012): 216–19. http://dx.doi.org/10.4028/www.scientific.net/amr.466-467.216.

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Palladium chloride anchored on polystyrene modified by 5-amino-1,10-phenanthroline was prepared and used as catalysts for the Suzuki cross-coupling reactions of aryl halide with arylboronic acid in supercritical carbon dioxide without use of organic solvent. The heterogeneous catalyst revealed excellent and recoverable catalytic performance for a wide range of aryl halides substrates. It can be easily separated from the reaction mixture and reused for six recycles without significant loss of catalytic activity.

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14

Zhang, Jing, Shihan Liu, Tao Zhang, Tao Liu, and Yu Lan. "Oxidation of Pd(ii) with disilane in a palladium-catalyzed disilylation of aryl halides: a theoretical view." Dalton Transactions 50, no. 22 (2021): 7656–66. http://dx.doi.org/10.1039/d1dt00399b.

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15

Franco, Mario, Emily L. Vargas, Mariola Tortosa, and M. Belén Cid. "Coupling of thiols and aromatic halides promoted by diboron derived super electron donors." Chemical Communications 57, no. 88 (2021): 11653–56. http://dx.doi.org/10.1039/d1cc05294b.

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Diboron-based super electron donors (SEDs) efficiently catalyze the coupling between thiols and aryl halides through a SRN1 mechanism. Remarkably, under the optimized conditions, the competitive borylation reaction of the aryl halides is suppressed.

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16

Liang, Kangjiang, Tao Li, Na Li, et al. "Redox-neutral photochemical Heck-type arylation of vinylphenols activated by visible light." Chemical Science 11, no. 8 (2020): 2130–35. http://dx.doi.org/10.1039/c9sc06184c.

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A regioselective and stereoselective Heck-type arylation of vinylphenols with non-activated (hetero)aryl halides was realized under visible light irradiation. The vinylphenolate anions acted as strong reducing photoactivators to activate (hetero)aryl halides.

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17

Koranne, Anushka, Shrishty Turakhia, Vikesh Kumar Jha, et al. "The Mizoroki–Heck reaction between in situ generated alkenes and aryl halides: cross-coupling route to substituted olefins." RSC Advances 13, no. 32 (2023): 22512–28. http://dx.doi.org/10.1039/d3ra03533f.

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This review covers palladium-catalyzed typical Mizoroki–Heck cross-coupling reactions of aryl halides with in situ generated alkenes, to form substituted olefins unlike direct cross-coupling of alkenes with aryl halides in Heck olefination.

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18

Mei, Tian-Sheng, Yue-Gang Chen, Xue-Tao Xu, et al. "Transition-Metal-Catalyzed Carboxylation of Organic Halides and Their Surrogates with Carbon Dioxide." Synthesis 50, no. 01 (2017): 35–48. http://dx.doi.org/10.1055/s-0036-1590908.

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Carbon dioxide is not only an essential component of ‘greenhouse gases’, but also an abundant, renewable C1 feedstock in organic synthesis. The catalytic incorporation of carbon dioxide into value-added chemicals to produce carboxylic acids has received enormous attention. This review summarizes recent developments in the transition-metal-catalyzed carboxylation of organic halides and their surrogates, such as aryl, vinyl, and alkyl halides and pseudohalides.1 Introduction2 Carboxylation of Aryl Halides and Pseudohalides3 Carboxylation of Vinyl Halides and Pseudohalides4 Carboxylation of Benzy

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19

Xu, Hui, and Ling-Ling Fan. "Microwave-assisted N-Arylation of Indoles via C(sp2)–N(sp2) Bond Formation by Aromatic Nucleophilic Substitution Reactions." Zeitschrift für Naturforschung B 63, no. 3 (2008): 298–302. http://dx.doi.org/10.1515/znb-2008-0313.

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Microwave-assisted nucleophilic aromatic substitution on aryl halides with different indoles is described. Moderate to good yields are obtained in short reaction time (25 - 40 min) when coupling indoles with fluoro- and chloro-substituted aryl halides under catalyst-free conditions.

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20

Malysheva, S. F., V. A. Kuimov, and S. N. Arbuzova. "Elemental Phosphorus in the Synthesis of Organophosphorus Compounds: The Recent Advances (A Review)." Russian Journal of General Chemistry 93, S1 (2023): S238—S255. http://dx.doi.org/10.1134/s1070363223140293.

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Abstract Recent publications on direct reactions of elemental phosphorus with organic halides (alkyl bromides, aryl (and hetaryl) halides, and aryl (and hetaryl) methyl halides) in the presence of superbasic and micellar catalysts are considered. The development of effective, technologically and environmentally acceptable methods for obtaining alkyl(and benzyl)-H-phosphinic and alkylphosphonic acids, triaryl(and hetaryl)phosphines and hetarylmethylphosphine oxides based on the above reactions is analyzed.

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21

Li, Yuewen, Danqing Zheng, Zhenhua Li, and Jie Wu. "Generation of N-aminosulfonamides via a photo-induced fixation of sulfur dioxide into aryl/alkyl halides." Organic Chemistry Frontiers 3, no. 5 (2016): 574–78. http://dx.doi.org/10.1039/c6qo00060f.

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A catalyst-free aminosulfonylation through insertion of sulfur dioxide with aryl/alkyl halides enabled by photoenergy is presented. Under ultraviolet irradiation, a three-component reaction of aryl/alkyl halides, sulfur dioxide, and hydrazines proceeds under mild conditions without any metals or photo-redox catalysts.

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22

Torvisco, Ana, Judith Binder, Melanie Wolf, et al. "Crystallographic studies of novel aryl heavy Group 14/15 halides and hydrides." Acta Crystallographica Section A Foundations and Advances 70, a1 (2014): C676. http://dx.doi.org/10.1107/s2053273314093231.

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A series of novel aryl (phenyl, tolyl, xylyl, mesityl, naphthyl, anthracenyl) heavy Group 14 and 15 halides (Cl, Br) and hydrides have been synthesized and structurally characterized via X-ray diffraction. Depending on the nature of the aryl substituent, these compounds display a range of non-covalent intermolecular interactions in the form of edge to face, π-π stacking and C-H···π interactions resulting in discrete arrangements in the solid state. The strength of these interactions as well as halide or hydride substituent effects and their consequences on resulting structural parameters will

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23

Wu, Shuai, Jin Shi, and Cheng-Pan Zhang. "Cu-Mediated arylselenylation of aryl halides with trifluoromethyl aryl selenonium ylides." Organic & Biomolecular Chemistry 17, no. 32 (2019): 7468–73. http://dx.doi.org/10.1039/c9ob01506j.

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24

Liu, Mingyang, Zhanrong Zhang, Huizhen Liu, Tianbin Wu, and Buxing Han. "Dehydroxyalkylative halogenation of C(aryl)–C bonds of aryl alcohols." Chemical Communications 56, no. 52 (2020): 7120–23. http://dx.doi.org/10.1039/d0cc02306j.

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Aryl alcohols which acted as aromatic electrophilic and radical synthetic equivalents were effectively converted to aryl halides via Cu mediated side-directed dehydroxyalkylative halogenation of C(aryl)–C bonds.

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25

Matsuda, Takanori, Takeshi Matsumoto, and Akira Murakami. "Palladium-Catalyzed Ring-Opening Coupling of Cyclobutenols with Aryl Halides." Synlett 29, no. 06 (2017): 754–58. http://dx.doi.org/10.1055/s-0036-1589117.

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A palladium(0)-catalyzed ring-opening cross-coupling reaction between tert-cyclobutenols and aryl halides produces γ-arylated β,γ-unsaturated ketones. In the case of aryl halides bearing functional groups at the ortho position, the resulting ring-opened ketones undergo intramolecular condensation to afford bicyclic aromatic compounds.

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26

Yang, S. H., C. S. Li, and C. H. Cheng. "Halide exchange reactions between aryl halides and alkali halides catalyzed by nickel metal." Journal of Organic Chemistry 52, no. 4 (1987): 691–94. http://dx.doi.org/10.1021/jo00380a041.

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27

Nagaki, Aiichiro, Yuki Uesugi, Yutaka Tomida, and Jun-ichi Yoshida. "Homocoupling of aryl halides in flow: Space integration of lithiation and FeCl3 promoted homocoupling." Beilstein Journal of Organic Chemistry 7 (August 2, 2011): 1064–69. http://dx.doi.org/10.3762/bjoc.7.122.

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The use of FeCl3 resulted in a fast homocoupling of aryllithiums, and this enabled its integration with the halogen–lithium exchange reaction of aryl halides in a flow microreactor. This system allows the homocoupling of two aryl halides bearing electrophilic functional groups, such as CN and NO2, in under a minute.

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28

Ishida, H., and H. Nakajima. "Preparation of aryl alcohols from aryl halides." Zeolites 15, no. 4 (1995): 383. http://dx.doi.org/10.1016/0144-2449(95)99140-i.

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29

Osako, Takao, Reinhard Kaiser, Kaoru Torii, and Yasuhiro Uozumi. "Aqueous Flow Hydroxycarbonylation of Aryl Halides Catalyzed by an Amphiphilic Polymer-Supported Palladium–Diphenylphosphine Catalyst." Synlett 30, no. 08 (2019): 961–66. http://dx.doi.org/10.1055/s-0037-1611769.

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An aqueous continuous-flow reaction system is developed for the palladium-catalyzed hydroxycarbonylation of aryl halides. Flow hydroxycarbonylation of aryl halides in aqueous solution proceeds efficiently in a flow reactor containing a palladium–diphenylphosphine complex immobilized on an amphiphilic polystyrene–poly(ethylene glycol) resin to give the corresponding benzoic acids in excellent yields.

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30

Smith, Craig D., and Alison Thompson. "The Suzuki–Miyaura reaction of BPin-substituted F-BODIPYs with aryl halides." Canadian Journal of Chemistry 99, no. 3 (2021): 287–94. http://dx.doi.org/10.1139/cjc-2020-0300.

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F-BODIPYs substituted with BPin functionality have been coupled to aryl halides using a mild and efficient catalyst system involving Pd2(dba)3 and XPhos. The methodology enables the Suzuki–Miyaura cross-coupling of electron-rich, electron-poor, and sterically encumbered BPin-substituted F-BODIPYs to aryl halides bearing various functional groups, thus presenting an opportunity for the preparation of highly functionalised F-BODIPYs without need for the corresponding aryl moiety to be available in borylated form.

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31

Wieber, Markus, and Ingbert Sauer. "Synthese gemischtsubstituierter Triorganobismutane / Synthesis of Mixed Substituted Triorganobismuthanes." Zeitschrift für Naturforschung B 40, no. 11 (1985): 1476–80. http://dx.doi.org/10.1515/znb-1985-1109.

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Sodium dimethylbismuthide, generated from dimethylbismuth bromide and sodium in liquid ammonia, was treated with alkyl halides to produce dimethylalkylbismuthanes, Me2Bi(alk) (alk = C2H5, n-C3H7, n-C4H9, C3H5, i-C3H7) as thermolabile liquids in yields ranging from 70 to 90%. With methylene chloride bis(dimethylbismutho)methane, (Me2Bi)2CH2, was obtained. Aryldimethylbismuthanes, (aryl)BiMe2, were prepared by treating dimethylbismuth bromide in THF with elemental lithium (-78 °C) and subsequent reaction with aryl halides (aryl = 4-C6H4CH3, 4-C6H4OCH3, 2,4,6-C6H2(CH3)3). At 90 °C in an N2-stream

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32

Chen, Kai, Man Sing Cheung, Zhenyang Lin, and Pengfei Li. "Metal-free borylation of electron-rich aryl (pseudo)halides under continuous-flow photolytic conditions." Organic Chemistry Frontiers 3, no. 7 (2016): 875–79. http://dx.doi.org/10.1039/c6qo00109b.

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33

Steller, Beate G., Berenike Doler, and Roland C. Fischer. "Diaryltin Dihydrides and Aryltin Trihydrides with Intriguing Stability." Molecules 25, no. 5 (2020): 1076. http://dx.doi.org/10.3390/molecules25051076.

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In the last few decades, organotin hydrides have proven their potential as building blocks for a great variety of organometallic compounds. In this context, organotin hydrides with sterically shielding aryl substituents have attracted special interest, as these ligands can kinetically stabilize metastable products. The selective synthesis of aryltin halide compounds Ar*2SnCl2 and Ar*SnI3 featuring the highly sterically encumbered aryl ligand Ar* (iPrAr* = 2,6-(Ph2CH)2-4-iPrC6H2; MeAr* = 2,6-(Ph2CH)2-4-MeC6H2) is presented. These aryltin halides were converted into corresponding aryltin hydride

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34

Ito, Hajime, Eiji Yamamoto, and Satoshi Ukigai. "Formal Nucleophilic Silyl Substitution of Aryl Halides with Silyllithium Reagents via Halogenophilic Attack of Silyl Nucleophiles." Synlett 28, no. 18 (2017): 2460–64. http://dx.doi.org/10.1055/s-0036-1590835.

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A new reaction has been developed for the formal nucleophilic silyl substitution of aryl halides with silyllithium or silylpotassium reagents. Dimethylphenylsilyllithium reacted with various aryl halides to form the corresponding arylsilanes in moderate to good yields with concomitant formation of the disilanes under the optimized reaction conditions. Mechanistic studies indicated that this silyl substitution reaction progresses through polar halogenophilic attack of silyl nucleophiles.

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35

Lee, Han-Sheng, Shao-Hsuan Pai, Wei-Ting Liao, Xin-Jing Yang, and Fu-Yu Tsai. "Mono and double Mizoroki–Heck reaction of aryl halides with dialkyl vinylphosphonates using a reusable palladium catalyst under aqueous medium." RSC Advances 7, no. 54 (2017): 34293–99. http://dx.doi.org/10.1039/c7ra06464k.

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36

Lyakhovich, Maria S., Alexei D. Averin, Olga K. Grigorova, Vitaly A. Roznyatovsky, Olga A. Maloshitskaya, and Irina P. Beletskaya. "Cu(I)- and Pd(0)-Catalyzed Arylation of Oxadiamines with Fluorinated Halogenobenzenes: Comparison of Efficiency." Molecules 25, no. 5 (2020): 1084. http://dx.doi.org/10.3390/molecules25051084.

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The comparison of the possibilities of Pd- and Cu-catalyzed amination reactions using fluorine-containing aryl bromides and iodides with oxadiamines to produce their N,N′-diaryl derivatives was carried out. The dependence of the reactivity of the aryl halides on the nature of the substituents and halogen atoms as well as on the structure of oxadiamines was investigated. It was found that the copper-catalyzed reactions were somewhat comparable with the palladium-mediated processes in the majority of cases, especially in the reactions with para-fluorine- and para-(trifluoromethyl)-substituted ar

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37

Lipilin, Dmitry L., Alexander E. Frumkin, Alexey Y. Tyurin, Vitalij V. Levin, and Alexander D. Dilman. "Photoredox Catalyzed Dealkylative Aromatic Halogen Substitution with Tertiary Amines." Molecules 26, no. 11 (2021): 3323. http://dx.doi.org/10.3390/molecules26113323.

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A reaction of aromatic halides bearing electron-withdrawing groups with tertiary amines in the presence of an iridium catalyst under blue light irradiation is described. Products of the aromatic substitution of the halide by the dialkylamino fragment are obtained. The interaction of aryl radicals with tertiary amines to generate zwitterionic radical species is believed to be the key factor responsible for the reaction efficiency.

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38

Lissel, Manfred, Jürgen Kottmann, Dov Tamarkin, and Mordechai Rabinovitz. "Reductive Cleavage of Aryl-O-and Aryl-CI- Bonds by C8K: a Potential Method for the Degradation of Dioxins." Zeitschrift für Naturforschung B 43, no. 9 (1988): 1211–12. http://dx.doi.org/10.1515/znb-1988-0922.

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39

Zhang, Yimin, Iiu, and Junmin Chen. "Efficient Synthesis of Diaryl Sulfides by Copper-catalysed Coupling of Aryl Halides and Thioacetate in Water." Journal of Chemical Research 37, no. 1 (2013): 19–21. http://dx.doi.org/10.3184/174751912x13545509224571.

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A simple economical, and highly efficient catalytic system for the synthesis of diaryl sulfides by a copper-catalysed coupling of aryl halides and thioacetate in water has been developed. A variety of aryl halides reacted with thioacetate to give the desired products in high yields up to 95%. The present catalysis protocol tolerated a wide range of functional groups, including amino, fluoro, and carboxyl moieties.

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40

Liu, Yan, Hui Peng, Jia Yuan, et al. "An efficient indenyl-derived phosphine ligand for the Suzuki–Miyaura coupling of sterically hindered aryl halides." Organic & Biomolecular Chemistry 14, no. 20 (2016): 4664–68. http://dx.doi.org/10.1039/c6ob00096g.

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An air-stable aryl substituted indenyl phosphine used in combination with Pd(OAc)<sub>2</sub> provides a highly efficient catalyst for the Suzuki–Miyaura cross-coupling reaction of sterically hindered aryl halides with aryl boronic acids.

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41

Chen, Kai, Pei He, Shuai Zhang, and Pengfei Li. "Synthesis of aryl trimethylstannanes from aryl halides: an efficient photochemical method." Chemical Communications 52, no. 58 (2016): 9125–28. http://dx.doi.org/10.1039/c6cc01135g.

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An efficient transition-metal-free photochemical method featuring excellent functional group tolerance, mild reaction conditions and short reaction times has been discovered and developed for the synthesis of (hetero)aryl trimethylstannanes from (hetero)aryl halides.

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42

Delaney, Connor P., Eva Lin, Qinan Huang, et al. "Cross-coupling by a noncanonical mechanism involving the addition of aryl halide to Cu(II)." Science 381, no. 6662 (2023): 1079–85. http://dx.doi.org/10.1126/science.adi9226.

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Copper complexes are widely used in the synthesis of fine chemicals and materials to catalyze couplings of heteroatom nucleophiles with aryl halides. We show that cross-couplings catalyzed by some of the most active catalysts occur by a mechanism not previously considered. Copper(II) [Cu(II)] complexes of oxalamide ligands catalyze Ullmann coupling to form the C–O bond in aryl ethers by concerted oxidative addition of an aryl halide to Cu(II) to form a high-valent species that is stabilized by radical character on the oxalamide ligand. This mechanism diverges from those involving Cu(I) and Cu(

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43

Che, Zhiping, and Hui Xu. "One-pot Synthesis of Dibenzofurans via SNAr and Subsequent Ligand-free Palladium-catalyzed Intramolecular Aryl-aryl Cross-coupling Reactions under Microwave Irradiation." Zeitschrift für Naturforschung B 66, no. 8 (2011): 833–36. http://dx.doi.org/10.1515/znb-2011-0808.

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An efficient one-pot synthesis of dibenzofurans, via SNAr reaction of aryl halides and ortho-bromophenols in the presence of anhydrous K2CO3 and subsequent ligand-free palladium-catalyzed intramolecular aryl-aryl cross-coupling cyclization under microwave irradiation, is described.

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44

Neetha, Mohan, C. M. A. Afsina, Thaipparambil Aneeja, and Gopinathan Anilkumar. "Recent advances and prospects in the palladium-catalyzed cyanation of aryl halides." RSC Advances 10, no. 56 (2020): 33683–99. http://dx.doi.org/10.1039/d0ra05960a.

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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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46

Junghare, Nilesh, Pravin Kadam, Jotiram Chavan, Minakshi Patil, and Gurunath Chougale. "A Highly Efficient, Catalyst-Free Synthesis of S-Alkyl/aryl Dithiocarbamate Derivatives under Green Conditions and Evaluation of their Biological Activity." Asian Journal of Chemistry 35, no. 11 (2023): 2703–7. http://dx.doi.org/10.14233/ajchem.2023.28324.

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An efficient, feasible, transition metal catalyst-free and environmental friendly approach for the synthesis of dithiocarbamate in an ethanol-water solvent combination at room temperature has been established. Alkyl/aryl halide, carbon disulfide and secondary amine were condensed in one pot to produce a range of dithiocarbamate derivatives. Based on the results, the yields were higher when aliphatic amine reacted with benzyl halides as compared to alkyl halides. This method has the advantage of using no hazardous solvents. Other benefits of this method include producing compounds with a good y

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47

Xu, Zhicheng, Yunqing Xiao, Hong Ding, et al. "Palladium/N-Heterocyclic Carbene Catalyzed Mono- and Double-Cyanation of Aryl Halides Using Potassium Ferrocyanide Trihydrate under Aerobic Conditions." Synthesis 47, no. 11 (2015): 1560–66. http://dx.doi.org/10.1055/s-0034-1379899.

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A practical palladium/N-heterocyclic carbene catalyzed procedure for the mono- and double-cyanation of aryl halides is described using inexpensive, easy-to-handle and nontoxic potassium ferrocyanide trihydrate {K4[Fe(CN)6]·3H2O} as the cyanating agent. The reaction does not require an anhydrous solvent, or the exclusion of air or moisture. A variety of electron-rich and electron-deficient aryl halides are efficiently converted into their corresponding nitriles and dicarbonitriles.

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48

Ma, Xuexiang, Aili Feng, Chengbu Liu, and Dongju Zhang. "Mechanistic insight into construction of axially chiral biaryls via palladium/chiral norbornene cooperative catalysis: a DFT-based computational study." Catalysis Science & Technology 12, no. 1 (2022): 105–15. http://dx.doi.org/10.1039/d1cy01863a.

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G., Avudaiappan, Palmurukan M. R., Unnikrishnan V., and Sreekumar K. "A polyamine dendritic polymer–copper complex: a reusable catalyst for the additive-free amination of aryl bromides, and iodides." New Journal of Chemistry 44, no. 4 (2020): 1477–84. http://dx.doi.org/10.1039/c9nj04981a.

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Additive-free synthesis of aryl amines from aryl halides using a reusable water-soluble porphyrin-cored amine-functionalized dendritic polymer copper complex (PPECH–Amine–Cu) catalyst in aqueous media.

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Liang, Kangjiang, Qian Liu, Lei Shen, et al. "Intermolecular oxyarylation of olefins with aryl halides and TEMPOH catalyzed by the phenolate anion under visible light." Chemical Science 11, no. 27 (2020): 6996–7002. http://dx.doi.org/10.1039/d0sc02160a.

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