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Автор: Grafiati

Опубліковано: 6 вересня 2023

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1

Rossi, Renzo, and Maurizio Ciofalo. "Palladium-Catalysed Intermolecular Direct C–H Bond Arylation of Heteroarenes with Reagents Alternative to Aryl Halides: Current State of the Art." Current Organic Chemistry 26, no. 3 (February 2022): 215–74. http://dx.doi.org/10.2174/1385272826666220201124008.

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Анотація:

Abstract: This unprecedented review with 322 references provides a critical up-to-date picture of the Pd-catalysed intermolecular direct C–H bond arylation of heteroarenes with arylating reagents alternative to aryl halides that include aryl sulfonates (aryl triflates, tosylates, mesylates, and imidazole-1-sulfonates), diaryliodonium salts, [(diacetoxy)iodo]arenes, arenediazonium salts, 1-aryltriazenes, arylhydrazines and N’-arylhydrazides, arenesulfonyl chlorides, sodium arenesulfinates, arenesulfinic acids, and arenesulfonohydrazides. Particular attention has been paid to summarise the preparation of the various arylating reagents and to highlight the practicality, versatility, and limitations of the various developed arylation protocols, also comparing their results with those achieved in analogous Pd-catalysed arylation reactions involving the use of aryl halides as electrophiles. Mechanistic proposals have also been briefly summarised and discussed. However, data concerning Pd-catalysed direct C–H bond arylations involving the C–H bonds of aryl substituents of the examined heteroarene derivatives have not been taken into account.

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2

Fischer, Carolin, and Burkhard Koenig. "Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds." Beilstein Journal of Organic Chemistry 7 (January 14, 2011): 59–74. http://dx.doi.org/10.3762/bjoc.7.10.

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Анотація:

N-Arylated aliphatic and aromatic amines are important substituents in many biologically active compounds. In the last few years, transition-metal-mediated N-aryl bond formation has become a standard procedure for the introduction of amines into aromatic systems. While N-arylation of simple aromatic halides by simple amines works with many of the described methods in high yield, the reactions may require detailed optimization if applied to the synthesis of complex molecules with additional functional groups, such as natural products or drugs. We discuss and compare in this review the three main N-arylation methods in their application to the synthesis of biologically active compounds: Palladium-catalysed Buchwald–Hartwig-type reactions, copper-mediated Ullmann-type and Chan–Lam-type N-arylation reactions. The discussed examples show that palladium-catalysed reactions are favoured for large-scale applications and tolerate sterically demanding substituents on the coupling partners better than Chan–Lam reactions. Chan–Lam N-arylations are particularly mild and do not require additional ligands, which facilitates the work-up. However, reaction times can be very long. Ullmann- and Buchwald–Hartwig-type methods have been used in intramolecular reactions, giving access to complex ring structures. All three N-arylation methods have specific advantages and disadvantages that should be considered when selecting the reaction conditions for a desired C–N bond formation in the course of a total synthesis or drug synthesis.

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3

Dodonova, Jelena, and Sigitas Tumkevicius. "Fused Pyrrolo[2,3-d]pyrimidines (7-Deazapurines) by Palladium-Catalyzed Direct N–H and C–H Arylation Reactions." Synthesis 49, no. 11 (March 2, 2017): 2523–34. http://dx.doi.org/10.1055/s-0036-1588734.

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Анотація:

Palladium-catalyzed intramolecular direct C–H arylations for the synthesis of hitherto unknown fused hetero systems containing an incorporated pyrrolo[2,3-d]pyrimidine scaffold are described. Pyrimido[5′,4′:4,5]pyrrolo[2,1-a]isoindoles were synthesized from 2,4-diarylpyrrolo[2,3-d]pyrimidines and o-bromobenzyl bromides by using a cascade N-benzylation/C–H arylation reaction sequence. A series of pyrimido[5′,4′:4,5]pyrrolo[1,2-f]phenanthridines were successfully assembled via a domino process involving the palladium-catalyzed direct double C–H arylation reactions of 2,4,7-triarylpyrrolo[2,3-d]pyrimidines with o-bromoiodobenzenes.

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4

Kepski, Konrad, and Wesley James Moran. "An Unexpected Reaction between Diaryliodonium Salts and DMSO." Organics 3, no. 3 (August 31, 2022): 275–80. http://dx.doi.org/10.3390/org3030020.

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Diaryliodonium salts are useful arylating reagents that have been exploited widely. In this Communication, we demonstrate that heating diphenyliodonium triflate in the solvent DMSO leads to an unexpected arylation reaction. It is postulated that arylation of DMSO at oxygen, followed by a thia-Sommelet–Hauser rearrangement, leads to the formation of 2-thiomethylphenols. More substituted diaryliodonium salts and cyclic diaryliodonium salts are shown to be more stable and less likely to react with DMSO. In conclusion, when using iodonium salts dissolved in DMSO, beware of side-reactions.

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5

Jeyachandran, Rajkumar, Harish Kumar Potukuchi, and Lutz Ackermann. "Copper-catalyzed CuAAC/intramolecular C–H arylation sequence: Synthesis of annulated 1,2,3-triazoles." Beilstein Journal of Organic Chemistry 8 (October 16, 2012): 1771–77. http://dx.doi.org/10.3762/bjoc.8.202.

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Анотація:

Step-economical syntheses of annulated 1,2,3-triazoles were accomplished through copper-catalyzed intramolecular direct arylations in sustainable one-pot reactions. Thus, catalyzed cascade reactions involving [3 + 2]-azide–alkyne cycloadditions (CuAAC) and C–H bond functionalizations provided direct access to fully substituted 1,2,3-triazoles with excellent chemo- and regioselectivities. Likewise, the optimized catalytic system proved applicable to the direct preparation of 1,2-diarylated azoles through a one-pot C–H/N–H arylation reaction.

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6

Urgoitia, Garazi, Maria Teresa Herrero, Fátima Churruca, Nerea Conde, and Raul SanMartin. "Direct Arylation in the Presence of Palladium Pincer Complexes." Molecules 26, no. 14 (July 20, 2021): 4385. http://dx.doi.org/10.3390/molecules26144385.

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Анотація:

Direct arylation is an atom-economical alternative to more established procedures such as Stille, Suzuki or Negishi arylation reactions. In comparison with other palladium sources and ligands, the use of palladium pincer complexes as catalysts or pre-catalysts for direct arylation has resulted in improved efficiency, higher reaction yields, and advantageous reaction conditions. In addition to a revision of the literature concerning intra- and intermolecular direct arylation reactions performed in the presence of palladium pincer complexes, the role of these remarkably active catalysts will also be discussed.

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7

Singh, Keisham. "Recent Advances in C–H Bond Functionalization with Ruthenium-Based Catalysts." Catalysts 9, no. 2 (February 12, 2019): 173. http://dx.doi.org/10.3390/catal9020173.

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Анотація:

The past decades have witnessed rapid development in organic synthesis via catalysis, particularly the reactions through C–H bond functionalization. Transition metals such as Pd, Rh and Ru constitute a crucial catalyst in these C–H bond functionalization reactions. This process is highly attractive not only because it saves reaction time and reduces waste,but also, more importantly, it allows the reaction to be performed in a highly region specific manner. Indeed, several organic compounds could be readily accessed via C–H bond functionalization with transition metals. In the recent past, tremendous progress has been made on C–H bond functionalization via ruthenium catalysis, including less expensive but more stable ruthenium(II) catalysts. The ruthenium-catalysed C–H bond functionalization, viz. arylation, alkenylation, annulation, oxygenation, and halogenation involving C–C, C–O, C–N, and C–X bond forming reactions, has been described and presented in numerous reviews. This review discusses the recent development of C–H bond functionalization with various ruthenium-based catalysts. The first section of the review presents arylation reactions covering arylation directed by N–Heteroaryl groups, oxidative arylation, dehydrative arylation and arylation involving decarboxylative and sp3-C–H bond functionalization. Subsequently, the ruthenium-catalysed alkenylation, alkylation, allylation including oxidative alkenylation and meta-selective C–H bond alkylation has been presented. Finally, the oxidative annulation of various arenes with alkynes involving C–H/O–H or C–H/N–H bond cleavage reactions has been discussed.

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8

Rosadoni, Elisabetta, Federico Banchini, Sara Bellini, Marco Lessi, Luca Pasquinelli, and Fabio Bellina. "Ligandless Palladium-Catalyzed Direct C-5 Arylation of Azoles Promoted by Benzoic Acid in Anisole." Molecules 27, no. 23 (December 2, 2022): 8454. http://dx.doi.org/10.3390/molecules27238454.

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Анотація:

The palladium-catalyzed direct arylation of azoles with (hetero)aryl halides is nowadays one of the most versatile and efficient procedures for the selective synthesis of heterobiaryls. Although this procedure is, due to its characteristics, also of great interest in the industrial field, the wide use of a reaction medium such as DMF or DMA, two polar aprotic solvents coded as dangerous according to environmental, health, safety (EHS) parameters, strongly limits its actual use. In contrast, the use of aromatic solvents as the reaction medium for direct arylations, although some of them show good EHS values, is poorly reported, probably due to their low solvent power against reagents and their potential involvement in undesired side reactions. In this paper we report an unprecedented selective C-5 arylation procedure involving anisole as an EHS green reaction solvent. In addition, the beneficial role of benzoic acid as an additive was also highlighted, a role that had never been previously described.

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9

Tarnowicz-Ligus, Stanisława, and Anna Trzeciak. "Heck Transformations of Biological Compounds Catalyzed by Phosphine-Free Palladium." Molecules 23, no. 9 (September 1, 2018): 2227. http://dx.doi.org/10.3390/molecules23092227.

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The development and optimization of synthetic methods leading to functionalized biologically active compounds is described. Two alternative pathways based on Heck-type reactions, employing iodobenzene or phenylboronic acid, were elaborated for the arylation of eugenol and estragole. Cinnamyl alcohol was efficiently transformed to saturated arylated aldehydes in reaction with iodobenzene using the tandem arylation/isomerization sequential process. The arylation of cinnamyl alcohol with phenylboronic acid mainly gave unsaturated alcohol, while the yield of saturated aldehyde was much lower. Catalytic reactions were carried out using simple, phosphine-free palladium precursors and water as a cosolvent, following green chemistry rules as much as possible.

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10

Bolm, Carsten, Jens P. Hildebrand, Kilian Muñiz, and Nina Hermanns. "Catalyzed Asymmetric Arylation Reactions." Angewandte Chemie International Edition 40, no. 18 (September 17, 2001): 3284–308. http://dx.doi.org/10.1002/1521-3773(20010917)40:18<3284::aid-anie3284>3.0.co;2-u.

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11

Christodoulou, Michael S., Egle M. Beccalli, and Sabrina Giofrè. "Palladium-Catalyzed Benzodiazepines Synthesis." Catalysts 10, no. 6 (June 6, 2020): 634. http://dx.doi.org/10.3390/catal10060634.

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Анотація:

This review is focused on palladium-catalyzed reactions as efficient strategies aimed at the synthesis of different classes of benzodiazepines. Several reaction typologies are reported including hydroamination, amination, C–H arylation, N-arylation, and the Buchwald–Hartwig reaction, depending on the different substrates identified as halogenated starting materials (activated substrates) or unactivated unsaturated systems, which then exploit Pd(0)- or Pd(II)-catalytic species. In particular, the use of the domino reactions, as intra- or intermolecular processes, are reported as an efficient and eco-compatible tool to obtain differently functionalized benzodiazepines. Different domino reaction typologies are the carboamination, aminoarylation, aminoacethoxylation, aminohalogenation, and aminoazidation.

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12

Mastalir, Ágnes, and Árpád Molnár. "On the Current Status of Ullmann-Type N-Arylation Reactions Promoted by Heterogeneous Catalysts." Inorganics 11, no. 7 (June 27, 2023): 276. http://dx.doi.org/10.3390/inorganics11070276.

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Анотація:

Ullmann-type C–N heterocoupling reactions have been applied for the syntheses of N-arylated amines. In the past decade, transition metal-catalyzed N-arylations have been recognized as particularly efficient procedures for the preparation of nitrogen-containing aromatic systems. These reactions typically carried out under optimized conditions, have also been found to be suitable for the synthesis of complex molecules with other functional groups, including natural products, drugs, or pharmaceuticals. Most importantly, copper-catalyzed N-arylations have been studied and employed in the total synthesis of biologically active compounds. The construction of fused N-heterocyclic compounds also remained the subject of extensive research because of their potential applications in drug discovery and the development of functional materials. The aim of this review is to summarize the recent progress in the synthetic applications of Ullmann-type N-arylation reactions performed in heterogeneous systems. In particular, the utilization of copper and palladium species immobilized on various support materials, modified by surface functionalization, has been discussed and evaluated.

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13

Zhang, Ling, Xiaoyan Lin, Dayun Huang, Xue Liu, and Xiangmei Wu. "Recent Advances in Triarylmethane Synthesis." Synthesis 52, no. 16 (May 14, 2020): 2311–29. http://dx.doi.org/10.1055/s-0040-1707115.

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Анотація:

Triarylmethanes are important molecules in organic chemistry. This review discusses advances in their synthesis summarized in five categories according to the starting materials: (1) benzyl reagents with different leaving groups, such as benzyl alcohols, ethers, esters, phosphates, sulfones, thioethers, sulfonamide, 1,3-dicarbonyls, and ammonium salts; (2) reactions via para- or ortho-quinone methides; (3) arylation of benzyl halides; (4) C–H activation of methylenes; and (5) reactions of aldehydes or N-tosylhydrazones. Triarylmethane derivatives such as 9-arylxanthenones, 9-arylfluorenes, and aryloxepines are also discussed.1 Introduction2 Benzyl Reagents with Leaving Groups3 Quinone Methide Mediated Reactions4 Arylation of Benzyl Halides5 C–H Activation of Methylene6 Reactions of Carbonyl Compounds7 Conclusions

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14

Finet, Jean Pierre. "Arylation reactions with organobismuth reagents." Chemical Reviews 89, no. 7 (November 1989): 1487–501. http://dx.doi.org/10.1021/cr00097a005.

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15

Della Ca’, Nicola. "Palladium-Catalyzed Reactions." Catalysts 11, no. 5 (April 30, 2021): 588. http://dx.doi.org/10.3390/catal11050588.

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Анотація:

Palladium is probably the most versatile and exploited transition metal in catalysis due to its capability to promote a myriad of organic transformations both at laboratory and industrial scales (alkylation, arylation, cyclization, hydrogenation, oxidation, isomerization, cross-coupling, cascade, radical reactions, etc [...]

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16

Gupta, Surabhi, Siddharth Baranwal, Nalluchamy Muniyappan, Shahulhameed Sabiah, and Jeyakumar Kandasamy. "Copper-Catalyzed N-Arylation of Sulfoximines with Arylboronic Acids under Mild Conditions." Synthesis 51, no. 10 (February 19, 2019): 2171–82. http://dx.doi.org/10.1055/s-0037-1612216.

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N-Arylation of sulfoximines with different arylboronic acids, including sterically hindered boronic acids, is achieved using copper(I) iodide and 4-DMAP at room temperature. Moreover, N-arylation of biologically relevant l-methionine sulfoximine is demonstrated for the first time. All these reactions provided the desired products in excellent yields within a short span of time. The optimized reaction conditions are well suited to the task of N-vinylation of sulfoximine with trans-2-phenylvinylboronic acid.

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17

Keske, Eric C., Brandon D. Moore, Olena V. Zenkina, Ruiyao Wang, Gabriele Schatte, and Cathleen M. Crudden. "Highly selective directed arylation reactions via back-to-back dehydrogenative C–H borylation/arylation reactions." Chem. Commun. 50, no. 69 (2014): 9883–86. http://dx.doi.org/10.1039/c4cc02499k.

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18

Terai, Seiya, Yuki Sato, Takuya Kochi, and Fumitoshi Kakiuchi. "Efficient synthesis of 3,6,13,16-tetrasubstituted-tetrabenzo[a,d,j,m]coronenes by selective C–H/C–O arylations of anthraquinone derivatives." Beilstein Journal of Organic Chemistry 16 (March 31, 2020): 544–50. http://dx.doi.org/10.3762/bjoc.16.51.

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An efficient synthesis of tetrabenzo[a,d,j,m]coronene derivatives having alkyl and alkoxy substituents at the 3, 6, 13, and 16-positions was achieved based on the ruthenium-catalyzed coupling reactions of anthraquinone derivatives with arylboronates via C–H and C–O bond cleavage. The reaction sequence involving the arylation, carbonyl methylenation, and oxidative cyclization effectively provided various tetrabenzo[a,d,j,m]coronenes in short steps from readily available starting materials. Tetrabenzo[a,d,j,m]coronenes possessing two different types of substituents were obtained selectively by sequential chemoselective C–O arylation and C–H arylation. The 1H NMR spectra of the tetrabenzo[a,d,j,m]coronene product indicated its self-assembling behavior in CDCl3.

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19

Wang, Xiaochen, Yuechen Li, Jianfeng Li, Yuan Zhang, Jinjun Shao, and Yongfang Li. "Direct Arylation Synthesis of Small Molecular Acceptors for Organic Solar Cells." Molecules 28, no. 8 (April 16, 2023): 3515. http://dx.doi.org/10.3390/molecules28083515.

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Анотація:

In recent years, small molecular acceptors (SMAs) have extensively promoted the progress of organic solar cells (OSCs). The facile tuning of chemical structures affords SMAs excellent tunability of their absorption and energy levels, and it gives SMA-based OSCs slight energy loss, enabling OSCs to achieve high power conversion efficiencies (e.g., >18%). However, SMAs always suffer complicated chemical structures requiring multiple-step synthesis and cumbersome purification, which is unfavorable to the large-scale production of SMAs and OSC devices for industrialization. Direct arylation coupling reaction via aromatic C-H bonds activation allows for the synthesis of SMAs under mild conditions, and it simultaneously reduces synthetic steps, synthetic difficulty, and toxic by-products. This review provides an overview of the progress of SMA synthesis through direct arylation and summarizes the typical reaction conditions to highlight the field’s challenges. Significantly, the impacts of direct arylation conditions on reaction activity and reaction yield of the different reactants’ structures are discussed and highlighted. This review gives a comprehensive view of preparing SMAs by direct arylation reactions to cause attention to the facile and low-cost synthesis of photovoltaic materials for OSCs.

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20

Kozyrod, RP, and JT Pinhey. "The Chemistry of Aryllead(IV) Tricarboxylates. The C-Arylation of Nitroalkanes and Nitronate Salts with Aryllead Triacetates." Australian Journal of Chemistry 38, no. 5 (1985): 713. http://dx.doi.org/10.1071/ch9850713.

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2-Nitropropane reacts with phenyllead triacetate in dimethyl sulfoxide to give 2-nitro-2-phenylpropane in good yield. This arylation of nitroalkanes has been examined with a variety of substrates and a number of aryllead triacetates, and in those cases where there was no steric hindrance the reaction was found to be quit general. Reactions of nitroethane and methyl nitroacetate, compounds with two α- hydrogens, were readily controlled to give either the mono- or di-arylated products. The corresponding nitronate salts were also examined and found to undergo the arylation reaction in similar yield but at a very much faster rate.

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21

Bolm, Carsten, Jens P. Hildebrand, Kilian Muniz, and Nina Hermanns. "ChemInform Abstract: Catalyzed Asymmetric Arylation Reactions." ChemInform 32, no. 50 (May 23, 2010): no. http://dx.doi.org/10.1002/chin.200150236.

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22

Lazzaroni, Simone, Daniele Dondi, Maurizio Fagnoni, and Angelo Albini. "Photochemical Arylation Reactions by 4-Chlorothioanisole." European Journal of Organic Chemistry 2007, no. 26 (September 2007): 4360–65. http://dx.doi.org/10.1002/ejoc.200700290.

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23

Kobiki, Yohsuke, Shin-ichi Kawaguchi, Takashi Ohe, and Akiya Ogawa. "Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides." Beilstein Journal of Organic Chemistry 9 (June 13, 2013): 1141–47. http://dx.doi.org/10.3762/bjoc.9.127.

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A novel method of photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides has been developed. Although the arylation reactions with triarylbismuthines are usually catalyzed by transition-metal complexes, the present arylation of diaryl diselenides with triarylbismuthines proceeds upon photoirradiation in the absence of transition-metal catalysts. A variety of unsymmetrical diaryl selenides can be conveniently prepared by using this arylation method.

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24

Escalante, Carlos H., Eder I. Martínez-Mora, Carlos Espinoza-Hicks, Alejandro A. Camacho-Dávila, Fernando R. Ramos-Morales, Francisco Delgado, and Joaquín Tamariz. "Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole." Beilstein Journal of Organic Chemistry 16 (June 17, 2020): 1320–34. http://dx.doi.org/10.3762/bjoc.16.113.

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Анотація:

A highly regio-, chemo- and stereoselective divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles is herein described, starting from 2-formylpyrrole and employing Diels–Alder and Heck arylation reactions. 3-(N-Benzyl-2-pyrrolyl)acrylates and 4-(pyrrol-2-yl)butenones underwent a highly endo-Diels–Alder cycloaddition with maleimides to furnish octahydropyrrolo[3,4-e]indoles, which served as precursors in the regioselective synthesis of aza-polycyclic skeletons via an intramolecular Heck arylation reaction. Through the latter reaction, the 3-(N-benzyl-2-pyrrolyl)acrylates give rise to 3-(pyrrolo[2,1-a]isoindol-3-yl)acrylates. A further oxidative aromatization of the polycyclic intermediates provides the corresponding polycyclic pyrrolo-isoindoles and isoindolo-pyrrolo-indoles. A theoretical study on the stereoselective Diels–Alder reactions, carried out by calculating the endo/exo transition states, revealed the assistance of non-covalent interactions in governing the endo stereocontrol.

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25

Raina, Gaurav, Prakash Kannaboina, Nagaraju Mupparapu, Sushil Raina, Qazi Naveed Ahmed, and Parthasarathi Das. "Programmed synthesis of triarylnitroimidazoles via sequential cross-coupling reactions." Organic & Biomolecular Chemistry 17, no. 8 (2019): 2134–47. http://dx.doi.org/10.1039/c9ob00144a.

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26

de Salas, Cristina, and Markus R. Heinrich. "Fixation and recycling of nitrogen monoxide through carbonitrosation reactions." Green Chem. 16, no. 6 (2014): 2982–87. http://dx.doi.org/10.1039/c3gc42432d.

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27

Keske, Eric C., Brandon D. Moore, Olena V. Zenkina, Ruiyao Wang, Gabriele Schatte, and Cathleen M. Crudden. "ChemInform Abstract: Highly Selective Directed Arylation Reactions via Back-to-Back Dehydrogenative C-H Borylation/Arylation Reactions." ChemInform 46, no. 4 (January 2015): no. http://dx.doi.org/10.1002/chin.201504198.

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28

Li, Yang, and Zhenyang Lin. "Understanding the reaction mechanisms of Pd-catalysed oxidation of alcohols and domino oxidation–arylation reactions using phenyl chloride as an oxidant." Org. Chem. Front. 1, no. 10 (2014): 1188–96. http://dx.doi.org/10.1039/c4qo00214h.

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29

Zhu, Shangrong, Xuechen Lu, Qiuneng Xu, Jian Li, and Shenghu Yan. "Cu-Catalyzed Cascade Reaction of Isoxazoles with Diaryliodonium Salts for the Synthesis of Acridines." Letters in Organic Chemistry 17, no. 12 (December 8, 2020): 944–50. http://dx.doi.org/10.2174/1570178617666200225125427.

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Анотація:

A straightforward and efficient synthesis of acridine derivatives via a copper-catalyzed cascade reaction among isoxazoles and diaryliodonium salts is achieved. Various mono-, multi-substituted and 9-substituted acridine derivatives could be obtained in moderate to good yields. The process has gone through tandem double arylation and Friedel-Crafts reactions.

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30

Liu, Yi, Puying Luo, Yang Fu, Tianxin Hao, Xuan Liu, Qiuping Ding, and Yiyuan Peng. "Recent advances in the tandem annulation of 1,3-enynes to functionalized pyridine and pyrrole derivatives." Beilstein Journal of Organic Chemistry 17 (September 22, 2021): 2462–76. http://dx.doi.org/10.3762/bjoc.17.163.

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Great progress has been made in the tandem annulation of enynes in the past few years. This review only presents the corresponding reactions of 1,3-enyne structural motifs to provide the functionalized pyridine and pyrrole derivatives. The functionalization reactions cover iodination, bromination, trifluoromethylation, azidation, carbonylation, arylation, alkylation, selenylation, sulfenylation, amidation, esterification, and hydroxylation. We also briefly introduce the applications of the products and the reaction mechanisms for the synthesis of corresponding N-heterocycles.

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31

Besson, Thierry, and Corinne Fruit. "Recent Advances in Transition-Metal-Free Late-Stage C-H and N-H Arylation of Heteroarenes Using Diaryliodonium Salts." Pharmaceuticals 14, no. 7 (July 11, 2021): 661. http://dx.doi.org/10.3390/ph14070661.

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Transition-metal-free direct arylation of C-H or N-H bonds is one of the key emerging methodologies that is currently attracting tremendous attention. Diaryliodonium salts serve as a stepping stone on the way to alternative environmentally friendly and straightforward pathways for the construction of C-C and C-heteroatom bonds. In this review, we emphasize the recent synthetic advances of late-stage C(sp2)-N and C(sp2)-C(sp2) bond-forming reactions under metal-free conditions using diaryliodonium salts as arylating reagent and its applications to the synthesis of new arylated bioactive heterocyclic compounds.

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32

Biehl, Edward R., and Subhash P. Khanapure. "Synthesis of polycyclics via aryne arylation reactions." Accounts of Chemical Research 22, no. 8 (August 1989): 275–81. http://dx.doi.org/10.1021/ar00164a003.

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33

Moiseev, Dmitry V., Vera A. Morugova, Alexey V. Gushchin, and Victor A. Dodonov. "Use of triarylstibines in C -arylation reactions." Tetrahedron Letters 44, no. 15 (April 2003): 3155–57. http://dx.doi.org/10.1016/s0040-4039(03)00511-2.

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34

Yasukawa, Tomohiro, Hiroyuki Miyamura, and Shu̅ Kobayashi. "Chiral Rhodium Nanoparticle-Catalyzed Asymmetric Arylation Reactions." Accounts of Chemical Research 53, no. 12 (December 1, 2020): 2950–63. http://dx.doi.org/10.1021/acs.accounts.0c00587.

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35

Ghosh, Indrajit, Leyre Marzo, Amrita Das, Rizwan Shaikh, and Burkhard König. "Visible Light Mediated Photoredox Catalytic Arylation Reactions." Accounts of Chemical Research 49, no. 8 (August 2, 2016): 1566–77. http://dx.doi.org/10.1021/acs.accounts.6b00229.

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36

Panda, Niranjan, Ashis Kumar Jena, and Sasmita Mohapatra. "Heterogeneous magnetic catalyst for S-arylation reactions." Applied Catalysis A: General 433-434 (August 2012): 258–64. http://dx.doi.org/10.1016/j.apcata.2012.05.026.

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37

Penkett, Clive S., Rupert O. Sims, Richard French, Lauriane Dray, Stephen J. Roome, and Peter B. Hitchcock. "Palladium catalyzed arylation reactions of meta photocycloadducts." Chemical Communications, no. 17 (2004): 1932. http://dx.doi.org/10.1039/b404816d.

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38

Livendahl, Madeleine, and Antonio M. Echavarren. "Palladium-Catalyzed Arylation Reactions: A Mechanistic Perspective." Israel Journal of Chemistry 50, no. 5-6 (December 2010): 630–51. http://dx.doi.org/10.1002/ijch.201000040.

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39

Protti, Stefano, Daniele Dondi, Maurizio Fagnoni, and Angelo Albini. "Photochemistry in synthesis: Where, when, and why." Pure and Applied Chemistry 79, no. 11 (January 1, 2007): 1929–38. http://dx.doi.org/10.1351/pac200779111929.

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A series of photochemical reactions are assessed under the environmental aspect by using Eissen and Metzger's EATOS (environmental assessment tool for organic syntheses) method and are compared with strictly analogous thermal processes. These include C-C bond-forming reactions (arylation and alkylation) and selective oxidation and reduction reactions. In most cases, the photochemical method is experimentally simpler and less expensive than the thermal alternative. A disadvantage is that photochemical reactions are carried out in rather dilute solution, and this factor gives by far the main contribution to the assessment. However, if the solvent is recovered, the photochemical reaction is more environment-friendly.

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40

Lu, Ju-You. "Copper-catalyzed synthesis of 2-aminopyridylbenzoxazolesviadomino reactions of intermolecularN-arylation and intramolecularO-arylation." RSC Advances 9, no. 24 (2019): 13414–17. http://dx.doi.org/10.1039/c9ra01908a.

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A simple and general approach to nitrogen-containing heterocyclesviacopper-catalyzed domino reaction has been developed, the corresponding 2-aminopyridylbenzoxazole derivatives were obtained in good to excellent yields using the readily available starting materials.

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41

Zheng, Peng-Fei, Yang An, Zuo-Yi Jiao, Zhou-Bao Shi та Fu-Min Zhang. "Comprehension of the α-Arylation of Nitroalkanes". Current Organic Chemistry 23, № 14 (16 жовтня 2019): 1560–80. http://dx.doi.org/10.2174/1385272823666190820113718.

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Background: α-Aryl substituted nitroalkanes are important synthetic intermediates for the preparation of pharmaceutical molecules, natural products, and functional materials. Due to their scare existence in Nature, synthesis of these compounds has attracted the attention of synthetic and medicinal chemists, rendering α-arylation of nitroalkanes of an important research topic. This article summarizes the important advances of α- arylation of nitroalkanes since 1963. Results: After a brief introduction of the synthetic application and the reactions of nitroalkanes, this article reviewed the synthetic methods for the α-arylated aliphatic nitro compound. The amount of research on α-arylation of nitroalkanes using various arylation reagents and the discovery of elegant synthetic approaches towards such skeleton have been discussed. This review described these advances in two sections. One is the arylation of non-activated nitroalkanes, with an emphasis on the application of diverse arylation reagents; the other focuses on the arylation of activated nitroalkanes, including dinitroalkanes, trinitroalkanes, α-nitrosulfones, α-nitroesters, α-nitrotoluenes, and α-nitroketones. The synthetic application of these methods has also been presented in some cases. Conclusion: In this review, we described the progress of α-arylation of nitroalkanes. Although the immense amount of research on α-arylation of aliphatic nitro compounds has been achieved, many potential issues still need to be addressed, especially the asymmetric transformation and its wide application in organic synthesis.

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42

Wang, Xiaochen, Kai Wang, and Mingfeng Wang. "Synthesis of conjugated polymers via an exclusive direct-arylation coupling reaction: a facile and straightforward way to synthesize thiophene-flanked benzothiadiazole derivatives and their copolymers." Polymer Chemistry 6, no. 10 (2015): 1846–55. http://dx.doi.org/10.1039/c4py01627k.

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43

Mateos-Gil, Jaime, Laura Rodríguez-Pérez, María Moreno Oliva, Georgios Katsukis, Carlos Romero-Nieto, Ma Ángeles Herranz, Dirk M. Guldi, and Nazario Martín. "Electroactive carbon nanoforms: a comparative study via sequential arylation and click chemistry reactions." Nanoscale 7, no. 3 (2015): 1193–200. http://dx.doi.org/10.1039/c4nr04365k.

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44

Wagner, Patrick, Maud Bollenbach, Christelle Doebelin, Frédéric Bihel, Jean-Jacques Bourguignon, Christophe Salomé, and Martine Schmitt. "t-BuXPhos: a highly efficient ligand for Buchwald–Hartwig coupling in water." Green Chem. 16, no. 9 (2014): 4170–78. http://dx.doi.org/10.1039/c4gc00853g.

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45

Kampmann, Sven S., Nikki Y. T. Man, Allan J. McKinley, George A. Koutsantonis, and Scott G. Stewart. "Exploring the Catalytic Reactivity of Nickel Phosphine–Phosphite Complexes." Australian Journal of Chemistry 68, no. 12 (2015): 1842. http://dx.doi.org/10.1071/ch15459.

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In this study, we present an investigation into various nickel phosphite and phosphite–phosphine complexes for use in the Mizoroki–Heck and Suzuki–Miyaura cross-coupling reactions and the ammonia arylation reaction. In these coupling reactions, it was discovered that the Ni[P(OEt)3]4, (dppf)Ni[P(OPh)3]2, and (binap)Ni[P(OPh)3]2 catalysts were the most effective. In addition, an optimisation process for these catalytic systems as well as functional group compatibility are discussed.

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46

Catellani, Marta, Elena Motti, Fiorenza Faccini, and Raffaella Ferraccioli. "New catalytic methods for the synthesis of selectively substituted aromatics through palladacycles." Pure and Applied Chemistry 77, no. 7 (January 1, 2005): 1243–48. http://dx.doi.org/10.1351/pac200577071243.

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Joint palladium and norbornene catalysis for selective aromatic functionalization via palladacycles is reported. Both alkylation and arylation of aromatics are considered after a brief outlook on the mechanism. These are multistep reactions that proceed in ordered sequences and are chemio-, regio-, and stereoselective. The study of the single steps with isolation of the organometallic species involved has allowed us to detect subtle steric and electronic effects which have been exploited to achieve catalytic reactions. Recent developments of aromatic alkylation and arylation are reported, in particular, condensed heterocyclic ring formation involving dialkylated arylpalladium complexes or both symmetrically and unsymmetrically substituted biphenylylpalladium complexes.

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47

Faradhiyani, Alanna, Qiao Zhang, Keisuke Maruyama, Junpei Kuwabara, Takeshi Yasuda, and Takaki Kanbara. "Synthesis of bithiazole-based semiconducting polymers via Cu-catalysed aerobic oxidative coupling." Materials Chemistry Frontiers 2, no. 7 (2018): 1306–9. http://dx.doi.org/10.1039/c7qm00584a.

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48

Snieckus, Victor, Livia da Frota, Cédric Schneider, Mauro de Amorim, and Alcides da Silva. "Chemoselective Ruthenium-Catalyzed C–O Bond Activation: Orthogonality of Nickel- and Palladium-Catalyzed Reactions for the Synthesis of Polyaryl Fluorenones." Synlett 28, no. 19 (November 14, 2017): 2587–93. http://dx.doi.org/10.1055/s-0036-1590985.

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Ruthenium-catalyzed C–O bond activation/arylation of methoxy and O-carbamoyl-substituted fluorenones is reported. Established are new reactions of compound 1 (X = H) to aryl (2) and 1,8-diaryl (3) fluorenones. Orthogonal ruthenium-, palladium- and nickel-catalyzed reactions with Suzuki–Miyaura reactions to afford 1,4-diaryl (4) and 1,4,8-triaryl fluorenones (5) are also described. The ready availability of starting methoxy fluorenones by directed ortho and remote metalation tactics confers facility to the presented reactions which may find application in material science areas. DFT calculations have been performed to rationalize the lack of C–H bond reactivity in the ruthenium-catalyzed reaction.

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49

Liu, Kun, Dirk Leifert, and Armido Studer. "Cooperative triple catalysis enables regioirregular formal Mizoroki–Heck reactions." Nature Synthesis 1, no. 7 (July 2022): 565–75. http://dx.doi.org/10.1038/s44160-022-00101-9.

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AbstractThe Mizoroki–Heck reaction between alkenes and aryl halides represents one of the most important methods for C−C bond formation in synthetic chemistry. Governed by their electronic and steric nature, alkenes are generally arylated with high regioselectivity, which conversely hampers diversity, in particular, if the regioirregular isomer is targeted. Usually, electron-poor alkenes selectively afford the corresponding β-coupled products, and achieving the opposite regioselectivity to obtain their α-arylated congeners is highly challenging. It would be desirable to access the irregular α-regioisomer by simple variation of the reaction conditions, keeping the standard substrates, thereby significantly enlarging the product space. Herein, we describe an intermolecular α-arylation of electron-poor alkenes through cooperative nickel, photoredox and sulfinate catalysis. This triple catalysis system operates under mild conditions and features excellent functional group tolerance. The orchestration of radical, transition metal and ionic bond-forming and -cleaving reactions in a single process is highly challenging, but certainly opens valuable doors in terms of reactivity. Moreover, the intermolecular α-arylation, α-alkenylation and α-alkynylation of styrenes could also be achieved through a one-pot process.

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50

Ngo, Thang Ngoc, Peter Ehlers, Tuan Thanh Dang, Alexander Villinger, and Peter Langer. "Synthesis of indolo[1,2-f]phenanthridines by Pd-catalyzed domino C–N coupling/hydroamination/C–H arylation reactions." Organic & Biomolecular Chemistry 13, no. 11 (2015): 3321–30. http://dx.doi.org/10.1039/c5ob00013k.

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