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Published: 18 May 2024

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1

Wang, Xi-Cun, Fang Wang, Zheng-Jun Quan, Man-Gang Wang, and Zheng Li. "An efficient and clean synthesis of 1-aroyl-3-aryl-4-substituted imidazole-2-thiones in water." Journal of Chemical Research 2005, no. 11 (November 2005): 689–90. http://dx.doi.org/10.3184/030823405774909423.

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Treatment 1-aryl-3-aroyl/benzofuroyl thioureas with α-bromo substituted carbonyl compounds in water affording 1-aroyl/benzofuroyl-3-aryl-4-substituted imidazole-2-thiones in excellent yields within short time.

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2

Steparuk, Elena V., Dmitrii L. Obydennov, and Vyacheslav Y. Sosnovskikh. "Synthesis of 5-Aroyl-2-aryl-3-hydroxypyridin-4(1H)-ones." Molbank 2023, no. 2 (June 10, 2023): M1668. http://dx.doi.org/10.3390/m1668.

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A two-stage synthesis of 5-aroyl-2-aryl-3-hydroxypyridin-4(1H)-ones (56–66% overall yields) was carried out by refluxing 5-aroyl-3-(benzyloxy)-2-(het)aryl-4H-pyran-4-ones with ammonium acetate in AcOH and subsequent debenzylation. The prepared N-unsubstituted 4-pyridones exist in the pyridone tautomeric form.

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3

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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4

Passananti, Monica, Flavio Cermola, Marina DellaGreca, Maria Rosaria Iesce, Lucio Previtera, Rosalia Sferruzza, and Fabio Temussi. "Photochemical Behaviour of Carbamates Structurally Related to Herbicides in Aqueous Media: Nucleophilic Solvent Trapping versus Radical Reactions." International Journal of Photoenergy 2014 (2014): 1–6. http://dx.doi.org/10.1155/2014/864361.

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Irradiation ofN-arylO-aryl carbamates has been carried out in H2O/CH3CN (1 : 1 v/v) solutions atλ>290 nm. When chlorine is on theN-aryl ring, halogen-substituted products are found. These photoproducts derive from the trapping of the intermediate radical cation by water and, even, by acetonitrile leading to phenols andN-arylacetamides (photo-Ritter products), respectively. UnsubstitutedN-aryl carbamates slowly undergo photo-Fries reaction.

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5

Jugelt, W. "Über Aryl-aroyl-diazomethane." Zeitschrift für Chemie 5, no. 12 (September 2, 2010): 455–56. http://dx.doi.org/10.1002/zfch.19650051206.

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6

Mkrtchyan, Satenik, Michał Jakubczyk, Suneel Lanka, Michael Pittelkow, and Viktor O. Iaroshenko. "Cu-Catalyzed Arylation of Bromo-Difluoro-Acetamides by Aryl Boronic Acids, Aryl Trialkoxysilanes and Dimethyl-Aryl-Sulfonium Salts: New Entries to Aromatic Amides." Molecules 26, no. 10 (May 16, 2021): 2957. http://dx.doi.org/10.3390/molecules26102957.

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We describe a mechanism-guided discovery of a synthetic methodology that enables the preparation of aromatic amides from 2-bromo-2,2-difluoroacetamides utilizing a copper-catalyzed direct arylation. Readily available and structurally simple aryl precursors such as aryl boronic acids, aryl trialkoxysilanes and dimethyl-aryl-sulfonium salts were used as the source for the aryl substituents. The scope of the reactions was tested, and the reactions were insensitive to the electronic nature of the aryl groups, as both electron-rich and electron-deficient aryls were successfully introduced. A wide range of 2-bromo-2,2-difluoroacetamides as either aliphatic or aromatic secondary or tertiary amides were also reactive under the developed conditions. The described synthetic protocols displayed excellent efficiency and were successfully utilized for the expeditious preparation of diverse aromatic amides in good-to-excellent yields. The reactions were scaled up to gram quantities.

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7

Bhaskar Reddy, Dandu, Biradavolu Seenaiah, Adivireddi Padmaja, and Pallela Venkata Ramana Reddy. "Synthesis of Some New Bis[1-(2-aroyl-3-aryl)cyclopropylcarbonyl]benzenes and Pyridines under Phase Transfer Catalysis (PTC) Method." Collection of Czechoslovak Chemical Communications 58, no. 6 (1993): 1437–44. http://dx.doi.org/10.1135/cccc19931437.

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Some new bis[1-(2-aroyl-3-aryl)cyclopropylcarbonyl]benzenes and pyridines IV - VI have been prepared by the cycloaddition of dimethylsulfonium phenacylide to 1,1'-(1,3-, 1,4-phenylene, and 2,6-pyridylene)-bis(3-aryl-2-propen-1-ones) I - III by adopting two different methods. The advantages of the PTC method over the other have been discussed. The structures of the compound have been confirmed by spectral data.

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8

Rasheed, O. K., I. R. Hardcastle, J. Raftery, and P. Quayle. "Aryne generation vs. Truce-Smiles and fries rearrangements during the Kobayashi fragmentation reaction: a new bi-aryl synthesis." Organic & Biomolecular Chemistry 13, no. 29 (2015): 8048–52. http://dx.doi.org/10.1039/c5ob01239b.

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9

Glaum, Marcus, Wolfgang Kläaui, Brian W. Skelton, and Allan H. White. "Synthesis, X-Ray Crystal Structure and Reactivity of [(tmeda)(p-tolyl)Pd(μ2-I)AgL], an Unusual Silver Iodide Complex; Reversible CO Insertion into the Pd-C Bond of [Pd(PPh3)(p-tolyl)L] (L - = [(C5H5)Co{P(OR)2O}3] - , R = Me, Pri)." Australian Journal of Chemistry 50, no. 11 (1997): 1047. http://dx.doi.org/10.1071/c97074.

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The palladium complexes [Pd(PPh3)(aryl)LOR] (aryl = Ph, p-tolyl; LOR¯ = [(C5H5)Co{P(OR)2O}3]¯, R = Me, Pri) have been prepared by reaction of [PdI(aryl)(tmeda)] (tmeda = N,N,N′,N′-tetramethyl-ethylenediamine) with the silver salts AgLOR in the presence of PPh3. The complexes [Pd(PPh3)(aryl)LOR] rapidly and reversibly insert carbon monoxide to yield the aroyl palladium complexes [Pd(PPh3)(C(O)- p-tolyl)LOR] (R = Me, Pri ). The palladium iodide complex [PdI(p-tolyl)(tmeda)] and the silver salt AgLOR in the absence of PPh3 form an unusual adduct [(p-tolyl)(tmeda)Pd(µ2-I)AgLOMe] that contains a short silver-iodide bond (Ag-I 2 · 703(1) Å). The silver-palladium bond is bridged by iodine (Pd-Ag 3 · 011(1), Pd{I 2 · 5934(9) Å) and the silver atom is coordinated by the tris-chelating oxygen ligand LOMe.

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10

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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11

Soni, Love Kumar, Tamanna Narsinghani, and Rica Jain. "Synthesis and Antibacterial Screening of Some 1-Aroyl-3-aryl Thiourea Derivatives." ISRN Medicinal Chemistry 2014 (January 29, 2014): 1–6. http://dx.doi.org/10.1155/2014/393102.

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A series of 1-aroyl-3-aryl thioureas derivatives were synthesized and evaluated for antibacterial activity. The results indicated that the compounds possessed higher activity against gram-negative bacteria than gram-positive bacteria. Amongst all these compounds, C18 (89.4%) exhibited the greatest antibacterial activity against gram-negative bacteria while C5 (85.6%) displayed maximum antibacterial activity against gram-positive bacteria. Preliminary study of the structure-activity relationship revealed that an electronic factor on aryl rings had a great effect on the antibacterial activity of these compounds.

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12

Singh, Surjeet, Pratik Yadav, Satya Narayan Sahu, Ismail Althagafi, Abhinav Kumar, Brijesh Kumar, Vishnu Ji Ram, and Ramendra Pratap. "Synthesis of 1-amino-2-aroyl/acetylnaphthalenes through a base mediated one pot inter and intramolecular C–C bond formation strategy." Org. Biomol. Chem. 12, no. 26 (2014): 4730–37. http://dx.doi.org/10.1039/c4ob00432a.

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13

Sathishkannan, Gopal, V. John Tamilarasan, and Kannupal Srinivasan. "Nucleophilic ring-opening reactions of trans-2-aroyl-3-aryl-cyclopropane-1,1-dicarboxylates with hydrazines." Organic & Biomolecular Chemistry 15, no. 6 (2017): 1400–1406. http://dx.doi.org/10.1039/c6ob02552h.

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trans-2-Aroyl-3-aryl-cyclopropane-1,1-dicarboxylates gave dihydropyrazoles when treated with arylhydrazines in refluxing EtOH, whereas they afforded cyclopropane-fused pyridazinones upon treatment with hydrazines in refluxing AcOH.

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14

Zhang, Tianyou, Jingyi Qiao, He Song, Feng Xu, Xiaochong Liu, Chunzhao Xu, Junjie Ma, Hao Liu, Zhizhong Sun, and Wenyi Chu. "Cu(OAc)2-Mediated benzimidazole-directed C–H cyanation using 2-(4-methylpiperazin-1-yl)acetonitrile as the cyano source." New Journal of Chemistry 43, no. 23 (2019): 9084–89. http://dx.doi.org/10.1039/c9nj00776h.

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15

Koch, Vanessa, and Stefan Bräse. "Pd-mediated cross-coupling of C-17 lithiated androst-16-en-3-ol – access to functionalized arylated steroid derivatives." Organic & Biomolecular Chemistry 15, no. 1 (2017): 92–95. http://dx.doi.org/10.1039/c6ob02496c.

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Herein, we report on Pd-mediated cross-coupling of vinyllithium steroids and aryl bromides to introduce various substituted aryls at C-17 of steroidal frameworks based on the structure of epi-androsterone.

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16

Linnemannstöns, Marvin, Jan Schwabedissen, Beate Neumann, Hans‐Georg Stammler, Raphael J. F. Berger, and Norbert W. Mitzel. "Aryl–Aryl Interactions in (Aryl‐Perhalogenated) 1,2‐Diaryldisilanes." Chemistry – A European Journal 26, no. 10 (January 30, 2020): 2169–73. http://dx.doi.org/10.1002/chem.201905727.

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17

Ying, Jun, Zhengjie Le, and Xiao-Feng Wu. "Palladium-catalyzed double-carbonylative cyclization of propargyl alcohols and aryl triflates to expedite construction of 4-aroyl-furan-2(5H)-ones." Organic Chemistry Frontiers 7, no. 18 (2020): 2757–60. http://dx.doi.org/10.1039/d0qo00874e.

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A palladium-catalyzed double-carbonylative cyclization of propargyl alcohols and aryl triflates has been developed. Various 4-aroyl-furan-2(5H)-one scaffolds were produced in good yields with Cr(CO)₆ as the CO source.

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18

Wang, Lizhong, Zhenjie Su, Siran Qian, Weijian Ye, and Cunde Wang. "Efficient Preparation of 2,3-Disubstituted Cyclopropane-1-Carbonitriles via Selective Decarboxylation of 1-Cyanocyclopropane-1-Carboxylates." Journal of Chemical Research 41, no. 11 (November 2017): 636–40. http://dx.doi.org/10.3184/174751917x15094552081161.

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2,3-Disubstituted cyclopropane-1-carbonitriles were efficiently formed via a selective decarboxylation reaction of substituted 2-aroyl-3-aryl-1-cyano-cyclopropane-1-carboxylates in up to 92% yield. The structures of three typical compounds were confirmed by X-ray crystallography.

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19

Higashino, Takeo, Masumi Takemoto, Akira Miyashita, and Eisaku Hayashi. "Aryl Migration of Heteroaromatics Having Aroyl Group." HETEROCYCLES 23, no. 1 (1985): 209. http://dx.doi.org/10.3987/r-1985-01-0209.

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20

Czarnecka, Anna, Emilia Kowalska, Agnieszka Bodzioch, Joanna Skalik, Marek Koprowski, Krzysztof Owsianik, and Piotr Bałczewski. "A selective removal of the secondary hydroxy group from ortho-dithioacetal-substituted diarylmethanols." Beilstein Journal of Organic Chemistry 14 (May 29, 2018): 1229–37. http://dx.doi.org/10.3762/bjoc.14.105.

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We present a successful deoxygenation reaction of ortho-1,3-dithianylaryl(aryl)methanols which enables a selective removal of the secondary hydroxy group in presence of the 1,3-dithianyl moiety under reductive conditions. This reaction proceeds well with ZnI2/Na(CN)BH3 in dichloroethane or benzene for both unsubstituted and substituted aryls (by electron-rich groups). This is leading to formyl-protected diarylmethanes with potential application in the synthesis of new pharmaceuticals and optoelectronic materials. This synthetic approach gives an access to a wide variety of functionalized ortho-1,3-dithianylaryl(aryl)methanes in 26–95% yields and is recommended for the substrates containing sulfur atoms, for which transition metal-induced reactions fail.

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21

Shemyakina, Olesya, Olga Volostnykh, Anton Stepanov, Igor Ushakov, and Tatyana Borodina. "Synthesis of Functionalized 5-Amino-3(2H)-furanones via Base-Catalyzed Ring-Cleavage/Recyclization of 4-Cyano-3(2H)-furanones in the Presence of Water." Synthesis 50, no. 24 (August 15, 2018): 4905–14. http://dx.doi.org/10.1055/s-0037-1609916.

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5-Alkyl/aryl/hetaryl-4-cyano-3(2H)-furanones undergo ring-cleavage/recyclization in the presence of water under mild conditions [MOH (M = Na, K), aqueous ethanol, 20–25 °C] to afford 4-acyl/aroyl/hetaroyl-5-amino-3(2Н)-furanones in 75–99% yields.

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22

Tanari, Yulinda, Darda Efendi, Roedhy Poerwanto, Didy Sopandie, and Ketty Suketi. "Aplikasi Kalsium dan NAA untuk Mengendalikan Getah Kuning Buah Manggis (Garcinia mangostana L.)." Jurnal Hortikultura Indonesia 9, no. 1 (April 2, 2018): 10–18. http://dx.doi.org/10.29244/jhi.9.1.10-18.

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ABSTRACTThe yellow sap is produced naturally in mangosteen organ except in the root. The yellow sap contaminated the aryl and rind if the epithelial cell walls rupture due to deficiency of calcium (Ca). Calcium is one of structural component of cell walls, whereas naphthaleneacetic acid (NAA) has its role in improving cell division and cell elongation. Interaction of Ca and NAA can improve sink strength and capacity because the newly formed cells need Ca to construct wall structure. This experiment aimed at finding out the effect of Ca and NAA applications in reducing the contamination of yellow sap in mangosteen. The experiment was conducted by using factorial random block design consisting of 2 factors and 3 replications. The first factor was Ca dosage (0 and 4.8 kg/tree), and the second factor was NAA concentration (0, 200, 400 and 600 ppm). The results showed that application of 4.8 Ca/tree and 200 ppm NAA as much as 5 ml / fruit effectively improve the content of Ca pectate in pericarp, reduced the percentage of yellow sap contamination on the fruit segment, aryl and rind to 0% and 12.3% respectively compared to control (17.8% on fruit segment, 36.8% on aryl and 56.1% on rind).Key words: aryl, Ca pectate, cell wall, middle lamela.ABSTRAKGetah kuning adalah getah yang dihasilkan secara alami pada setiap organ manggis, kecuali pada akar. Getah kuning akan keluar dan mencemari aril serta kulit jika dinding sel epitel pecah karena kekurangan kalsium (Ca). Kalsium adalah komponen dinding sel, berperan dalam struktur dan permeabilitas membran sedangkan asam naftalenasetat (NAA) berperan penting dalam meningkatkan pembelahan dan pembesaran sel. Interaksi keduanya dapat meningkatkan kapasitas sink buah karena sel yang baru terbentuk membutuhkan Ca dalam menyusun struktur dinding sel. Percobaan bertujuan untuk mengetahui pengaruh aplikasi Ca dan NAA dalam menurunkan cemaran getah kuning manggis. Percobaan menggunakan rancangan acak kelompok faktorial 2 faktor dengan 3 ulangan. Faktor ke-1 yaitu dosis Ca (0 dan 4.8 kg Ca/pohon) dan faktor ke-2 yaitu konsentrasi NAA (0, 200, 400 dan 600 ppm) dengan volume semprot 5 ml perbuah. Hasil percobaan menunjukkan bahwa aplikasi 4.8 kg Ca/pohon dengan NAA 200 ppm sebanyak 5 ml/buah efektif meningkatkan kandungan Ca pektat perikarp dan menurunkan persentase buah tercemar getah kuning menjadi 0% pada juring dan aril serta 12.3% pada kulit dibandingkan dengan perlakuan kontrol (17.8% pada juring, 36.8% pada aril dan 56.1% pada kulit buah).Kata kunci: aril, Ca pektat, dinding sel, lamela tengah

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23

Kramer, Søren. "Homogeneous Gold-Catalyzed Aryl–Aryl Coupling Reactions." Synthesis 52, no. 14 (April 2, 2020): 2017–30. http://dx.doi.org/10.1055/s-0039-1690882.

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Synthesis of biaryl motifs are crucial for the development and synthesis of pharmaceuticals, natural products, and functional materials. During the last decade, gold-catalyzed aryl–aryl coupling reactions have evolved from a curiosity to a well-established research field. This review summarizes the field from early examples up to the latest developments. Facile C–H functionalization and orthogonal reactivity compared to many other types of transition metal catalysis, for example, palladium catalysis, makes gold-catalyzed aryl–aryl coupling reactions highly appealing and valuable.1 Introduction2 Early Examples3 Cross-Coupling with External Oxidants4 Cross-Coupling without External Oxidants5 Conclusions

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24

Nagaki, Aiichiro, and Yosuke Ashikari. "Homogeneous Catalyzed Aryl–Aryl Cross-Couplings in Flow." Synthesis 53, no. 11 (January 18, 2021): 1879–88. http://dx.doi.org/10.1055/a-1360-7798.

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AbstractAryl–aryl cross-coupling reactions are important reactions for the production of various biaryl compounds. This short review covers the various aryl–aryl cross-coupling reactions carried out in flow, focusing on the metal species of the aryl nucleophiles used in the cross-coupling reactions.1 Introduction2 Suzuki–Miyaura Coupling (B)3 Migita–Kosugi–Stille Coupling (Sn)4 Negishi Coupling (Zn)5 Kumada–Tamao–Corriu Coupling (Mg)6 Murahashi Coupling (Li)7 Conclusion

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25

Kim, Yeojin, Kwang Ho Song, and Sunwoo Lee. "Synthesis of S-aryl thioesters via palladium-catalyzed thiocarbonylation of aryl iodides and aryl sulfonyl hydrazides." Organic Chemistry Frontiers 7, no. 19 (2020): 2938–43. http://dx.doi.org/10.1039/d0qo00748j.

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26

Kaminský, Jakub, Hana Dvořáková, Jan Štursa, and Jitka Moravcová. "Problems with a conformation assignment of aryl-substituted resorc[4]arenes." Collection of Czechoslovak Chemical Communications 76, no. 10 (2011): 1199–222. http://dx.doi.org/10.1135/cccc2010104.

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Acid-catalyzed condensation of resorcinol with 3,5-diisopropoxybenzaldehyde and 3,5-dihydroxybenzaldehyde afforded aryl substituted resorc[4]arenes 1a and 1b, respectively. All 16 hydroxyls in 1b were acetylated providing resorc[4]arene 1c. The conformational behaviour of 1a, 1b and 1c was studied by NMR spectroscopy and quantum chemical calculations. It was found that the stabilization of their conformations is an effect of competing π-π and OH-π interactions, hydrogen bonding and steric features, respectively. As a result, C2 symmetrical boat conformations 1a, 1b and 1c with aryls in axial positions were identified in all cases. In case of 1c also the formation of C2 symmetrical conformation with aryls in equatorial positions (boat-eq) was identified. Moreover, compounds 1a and 1b being able to create hydrogen bonds, adopt also symmetrical C4 crown conformations. For 1c(boat-ax), the boat-boat conversion with energy barrier of 80 kJ/mol was observed, while the 1c(boat-eq) was found to be rigid in the whole accessible temperature range. Both conformers of 1c exhibit also second dynamic process – rotation of bridge aryl rings (ΔG‡ = 66 kJ/mol).

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27

Utri, Gerhard, Karl-Eberhard Schwarzhans, and Günter M. Allmaier. "Ferrocenyl-aryl-plumbane / Ferrocenyl-aryl-plumbanes." Zeitschrift für Naturforschung B 45, no. 6 (June 1, 1990): 755–62. http://dx.doi.org/10.1515/znb-1990-0606.

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The first example of a diplumba[1.1]ferrocenophane[cpPb(ø2)cp]2Fe2 has been prepared from ø2PbCl2 and 1,1′-dilithioferrocene 2 TMEDA. The preparation of further four ferrocenyl-phenyl-plumbanes, including the hitherto unknown compounds (ø3Pbcp)2Fe, Fc2Pb2ø2 and [(ø3Pb)cpFecp]FcPbø2 has been achieved by reaction of a mixture of monolithioferrocene · TMEDA and 1,1′-dilithioferrocene 2 TMEDA with ø 2PbCl2 and ø3PbCl, respectively.These compounds have been investigated by 1H, 13C and 207Pb NMR spectroscopy as well as by half-wave potential measurements, EI, FD and PD mass spectrometry.The results were discussed in terms of the possibility of Pb/Fe metal orbital overlap.There is evidence from the VT 1H NMR spectra for conformational flexibility of the diplumba[ 1.1 ]ferrocenophane.

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28

Sapountzis, Ioannis, Wenwei Lin, Christiane C. Kofink, Christina Despotopoulou, and Paul Knochel. "Eisenkatalysierte Aryl-Aryl-Kreuzkupplungen mit Kupferreagentien." Angewandte Chemie 117, no. 11 (March 4, 2005): 1682–85. http://dx.doi.org/10.1002/ange.200462013.

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29

Wencel-Delord, Joanna, Corinna Nimphius, Frederic W. Patureau, and Frank Glorius. "[RhIIICp*]-katalysierte dehydrierende Aryl-Aryl-Bindungsknüpfung." Angewandte Chemie 124, no. 9 (January 27, 2012): 2290–94. http://dx.doi.org/10.1002/ange.201107842.

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30

Singh, Sonia, Mohammad H. Mosslemin, and Alireza Hassanabadi. "Synthesis of 5-Aryl-1,3-Dimethyl-7-Selenoxopyrimidino[4,5-d]Pyrimidine-2,4(1H,3H)-Dione." Journal of Chemical Research 42, no. 5 (May 1, 2018): 264–66. http://dx.doi.org/10.3184/174751918x15265512038216.

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A one-pot method for the synthesis of six novel 5-aryl-1,3-dimethyl-7-selenoxopyrimidino[4,5- d]pyrimidine-2,4(1 H,3 H)-diones in excellent yields at room temperature has been achieved via reaction between potassium selenocyanate and an aroyl chloride followed by the addition of 6-amino- N,N′-dimethyluracil.

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31

Cheng, Jiang, Rui Yang, Xiaopeng Wu, Song Sun, and Jin-Tao Yu. "Rhodium-Catalyzed Annulation of 2-Arylimidazoles and α-Aroyl Sulfoxonium Ylides toward 5-Arylimidazo[2,1-a]isoquinolines." Synthesis 50, no. 17 (June 28, 2018): 3487–92. http://dx.doi.org/10.1055/s-0037-1610124.

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A Rh-catalyzed annulation between 2-aryl-1H-benzo[d]imidazoles and α-aroyl sulfoxonium ylides was developed, affording a series of benzimidazo[2,1-a]isoquinolines in moderate to excellent yields. This procedure proceeded with the sequential ortho-C–H functionalization and cyclization, representing a facile and straightforward pathway to access such frameworks.

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32

Ribas, Xavi, Raül Xifra, and Xavier Fontrodona. "Bis-Phenoxo-CuII2 Complexes: Formal Aromatic Hydroxylation via Aryl-CuIII Intermediate Species." Molecules 25, no. 20 (October 9, 2020): 4595. http://dx.doi.org/10.3390/molecules25204595.

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Ullmann-type copper-mediated arylC-O bond formation has attracted the attention of the catalysis and organometallic communities, although the mechanism of these copper-catalyzed coupling reactions remains a subject of debate. We have designed well-defined triazamacrocyclic-based aryl-CuIII complexes as an ideal platform to study the C-heteroatom reductive elimination step with all kinds of nucleophiles, and in this work we focus our efforts on the straightforward synthesis of phenols by using H2O as nucleophile. Seven well-defined aryl-CuIII complexes featuring different ring size and different electronic properties have been reacted with water in basic conditions to produce final bis-phenoxo-CuII2 complexes, all of which are characterized by XRD. Mechanistic investigations indicate that the reaction takes place by an initial deprotonation of the NH group coordinated to CuIII center, subsequent reductive elimination with H2O as nucleophile to form phenoxo products, and finally air oxidation of the CuI produced to form the final bis-phenoxo-CuII2 complexes, whose enhanced stability acts as a thermodynamic sink and pushes the reaction forward. Furthermore, the corresponding triazamacrocyclic-CuI complexes react with O2 to undergo 1e− oxidation to CuII and subsequent C-H activation to form aryl-CuIII species, which follow the same fate towards bis-phenoxo-CuII2 complexes. This work further highlights the ability of the triazamacrocyclic-CuIII platform to undergo aryl-OH formation by reductive elimination with basic water, and also shows the facile formation of rare bis-phenoxo-CuII2 complexes.

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33

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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34

Yahav-Levi, Anette, Israel Goldberg, and Arkadi Vigalok. "Aryl-Halide versus Aryl−Aryl Reductive Elimination in Pt(IV)−Phosphine Complexes." Journal of the American Chemical Society 128, no. 27 (July 2006): 8710–11. http://dx.doi.org/10.1021/ja062166r.

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35

Ghosh, Manoj Kumar, and Nilendri Rout. "Aryl‐Aryl Cross‐Coupling with Hypervalent Iodine Reagents: Aryl Group Transfer Reactions." ChemistrySelect 5, no. 43 (November 18, 2020): 13644–55. http://dx.doi.org/10.1002/slct.202003396.

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36

Soleiman-Beigi, M., and Z. Arzehgar. "A Novel Method for the Direct Synthesis of Symmetrical and Unsymmetrical Sulfides and Disulfides from Aryl Halides and Ethyl Potassium Xanthogenate." Synlett 29, no. 07 (January 31, 2018): 986–92. http://dx.doi.org/10.1055/s-0037-1609081.

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An efficient and new method for the synthesis of disulfides and sulfides via the reaction of aryl halides with ethyl potassium xanthogenate in the presence of MOF-199 is described. O-Ethyl-S-aryl carbonodithioate has a key role as an intermediate in this procedure; it was converted into symmetrical diaryl disulfides in DMF. Additionally, this could be applied to the synthesis of unsymmetrical aryl alkyl(aryl′) disulfides by the reaction with S-alkyl(aryl) sulfurothioates (Bunte salts) as well as unsymmetrical aryl alkyl(aryl′) sulfides in DMSO.

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37

Porwal, Digvijay, and Martin Oestreich. "B(C6F5)3-Catalyzed Reduction of Sulfoxides and Sulfones to Sulfides with Hydrosilanes." Synthesis 49, no. 20 (July 5, 2017): 4698–702. http://dx.doi.org/10.1055/s-0036-1588476.

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B(C6F5)3 is shown to catalyze the deoxygenation of sulfoxides and sulfones to the corresponding sulfides with Et3SiH as the stoichiometric hydride source. While the method is limited in terms of functional group tolerance, it is applicable to the reduction of alkyl/aryl-, aryl/aryl-, and alkyl/alkyl-substituted sulfoxides, including the benzyl/benzyl-substituted derivative. The same protocol converts alkyl/aryl- but not aryl/aryl-substituted sulfones into sulfides.

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38

Cui, Mingyu, Dingkai Wang, Yanjun Li, Wei Zhao, Chong Liang, Xutang Liu, Shuiyuan Fu, Luyao Wang, and Xianyong Wei. "Preparation of magnetic silica supported Brønsted acidic ionic liquids for the depolymerization of lignin to aromatic monomers." New Journal of Chemistry 46, no. 9 (2022): 4167–78. http://dx.doi.org/10.1039/d1nj04777a.

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39

Leng, Yuting, Yangjie Wu, Shanshan Zhang, Chuang Liu, Xiaojun Wu, Wen Li, He Li, and Shiwei Wang. "Synthesis of 1,3,4-Oxadiazoles by Iodine-Mediated Oxidative Cyclization of Methyl Ketones with 4-Phenylsemicarbazide." Synlett 33, no. 03 (November 25, 2021): 269–72. http://dx.doi.org/10.1055/a-1707-0965.

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AbstractAn efficient one-pot method has been developed to access 5-amino-2-(het)aroyl-1,3,4-oxadiazoles through I2/DMSO-promoted oxidative cyclization of 4-phenylsemicarbazide with (het)aryl methyl ketones under mild conditions. This reaction proceeds smoothly with a wide range of methyl ketones containing various functional groups to give the corresponding products in moderate yields under mild conditions.

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40

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

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41

Castelani, Priscila, Silas Luque, and João V. Comasseto. "Dilithium aryl cyanocuprates from butyl aryl tellurides." Tetrahedron Letters 45, no. 23 (May 2004): 4473–75. http://dx.doi.org/10.1016/j.tetlet.2004.04.062.

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42

Wencel-Delord, Joanna, Corinna Nimphius, Frederic W. Patureau, and Frank Glorius. "[RhIIICp*]-Catalyzed Dehydrogenative ArylAryl Bond Formation." Angewandte Chemie International Edition 51, no. 9 (January 27, 2012): 2247–51. http://dx.doi.org/10.1002/anie.201107842.

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43

Chotana, Ghayoor A., Jose R. Montero Bastidas, Susanne L. Miller, Milton R. Smith, and Robert E. Maleczka. "One-Pot Iridium Catalyzed C–H Borylation/Sonogashira Cross-Coupling: Access to Borylated Aryl Alkynes." Molecules 25, no. 7 (April 10, 2020): 1754. http://dx.doi.org/10.3390/molecules25071754.

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Borylated aryl alkynes have been synthesized via one-pot iridium catalyzed C–H borylation (CHB)/Sonogashira cross-coupling of aryl bromides. Direct borylation of aryl alkynes encountered problems related to the reactivity of the alkyne under CHB conditions. However, tolerance of aryl bromides to CHB made possible a subsequent Sonogashira cross-coupling to access the desired borylated aryl alkynes.

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44

Himmelstrup, Jonas, Mikkel B. Buendia, Xing-Wen Sun, and Søren Kramer. "Enantioselective aryl–aryl coupling facilitated by chiral binuclear gold complexes." Chemical Communications 55, no. 86 (2019): 12988–91. http://dx.doi.org/10.1039/c9cc07175j.

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45

Chen, Xue, Yuan Liang, Wen-Wen Wang, Chengping Miao, Xue-Qiang Chu, Weidong Rao, Hao Xu, Xiaocong Zhou, and Zhi-Liang Shen. "Palladium-Catalyzed Esterification of Aryl Fluorosulfates with Aryl Formates." Molecules 29, no. 9 (April 26, 2024): 1991. http://dx.doi.org/10.3390/molecules29091991.

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An efficient palladium-catalyzed carbonylation of aryl fluorosulfates with aryl formates for the facile synthesis of esters was developed. The cross-coupling reactions proceeded effectively in the presence of a palladium catalyst, phosphine ligand, and triethylamine in DMF to produce the corresponding esters in moderate to good yields. Of note, functionalities or substituents, such as nitro, cyano, methoxycarbonyl, trifluoromethyl, methylsulfonyl, trifluoromethoxy, fluoro, chloro, bromo, methyl, methoxy, N,N-dimethyl, and [1,3]dioxolyl, were well-tolerated in the reactions, which could be kept for late-stage modification. The reactions employing readily available and relatively robust aryl fluorosulfates as coupling electrophiles could potentially serve as an attractive alternative to traditional cross-couplings with the use of aryl halides and pseudohalides as substrates.

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46

Wu, Xiao-Feng. "Palladium-catalyzed carbonylative transformation of aryl chlorides and aryl tosylates." RSC Advances 6, no. 87 (2016): 83831–37. http://dx.doi.org/10.1039/c6ra18388c.

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47

Agrawal, Toolika, and Silas P. Cook. "Iron-Catalyzed Coupling of Aryl Sulfamates and Aryl/Vinyl Tosylates with Aryl Grignards." Organic Letters 16, no. 19 (September 17, 2014): 5080–83. http://dx.doi.org/10.1021/ol5024344.

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48

Godt, Adelheid, Ömer Ünsal, and Mark Roos. "Synthesis of 3,5-Disubstituted 4-Hydroxybenzoates by Aryl−Aryl and Alkynyl−Aryl Coupling." Journal of Organic Chemistry 65, no. 9 (May 2000): 2837–42. http://dx.doi.org/10.1021/jo991907m.

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49

Wu, Xiongyu, Jenny K. Ekegren, and Mats Larhed. "Microwave-Promoted Aminocarbonylation of Aryl Iodides, Aryl Bromides, and Aryl Chlorides in Water." Organometallics 25, no. 6 (March 2006): 1434–39. http://dx.doi.org/10.1021/om051044p.

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50

Basu, Souradeep, Alexander H. Sandtorv, and David R. Stuart. "Imide arylation with aryl(TMP)iodonium tosylates." Beilstein Journal of Organic Chemistry 14 (May 11, 2018): 1034–38. http://dx.doi.org/10.3762/bjoc.14.90.

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Herein, we describe the synthesis of N-aryl phthalimides by metal-free coupling of potassium phthalimide with unsymmetrical aryl(TMP)iodonium tosylate salts. The aryl transfer from the iodonium moiety occurs under electronic control with the electron-rich trimethoxyphenyl group acting as a competent dummy ligand. The yields of N-aryl phthalimides are moderate to high and the coupling reaction is compatible with electron-deficient and sterically encumbered aryl groups.

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