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Journal articles on the topic 'Palladium-catalyzed substitutive coupling'

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Published: 7 September 2024

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1

Collet, Jurriën W., Thomas R. Roose, Bram Weijers, Bert U. W. Maes, Eelco Ruijter, and Romano V. A. Orru. "Recent Advances in Palladium-Catalyzed Isocyanide Insertions." Molecules 25, no. 21 (October 23, 2020): 4906. http://dx.doi.org/10.3390/molecules25214906.

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Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function as a CO-substitute in palladium-catalyzed cross couplings. Over the past decades, isocyanides have emerged as practical and versatile C1 building blocks, whose inherent N-substitution allows for the rapid incorporation of nitrogeneous fragments in a wide variety of products. Recent developments in palladium catalyzed isocyanide insertion reactions have significantly expanded the scope and applicability of these imidoylative cross-couplings. This review highlights the advances made in this field over the past eight years.

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2

Yuasa, Akihiro, Kazunori Nagao, and Hirohisa Ohmiya. "Allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions." Beilstein Journal of Organic Chemistry 16 (February 7, 2020): 185–89. http://dx.doi.org/10.3762/bjoc.16.21.

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The allylic cross-coupling using aromatic aldehydes as α-alkoxyalkyl anions is described. The synergistic palladium/copper-catalyzed reaction of aromatic aldehydes, allylic carbonates, and a silylboronate produces the corresponding homoallylic alcohol derivatives. This process involves the catalytic formation of a nucleophilic α-silyloxybenzylcopper(I) species and the subsequent palladium-catalyzed allylic substitution.

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3

Campbell, Katie, Robert McDonald, and Rik R. Tykwinski. "Porphyrinic assemblies of pyridine-containing macrocycles." Journal of Porphyrins and Phthalocyanines 09, no. 11 (November 2005): 794–802. http://dx.doi.org/10.1142/s1088424605000903.

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Using a combination of palladium-catalyzed cross-coupling and copper-catalyzed homocoupling reactions, two pyridine-containing macrocycles with varying pendant substitution were constructed. Their synthesis and subsequent coordination to a ruthenium porphyrin is described. In addition to synthetic details and characterization, an examination of their electronic properties is provided.

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4

Crawford, Sarah M., Craig A. Wheaton, Vinayak Mishra, and Mark Stradiotto. "Probing the effect of donor-fragment substitution in Mor-DalPhos on palladium-catalyzed C–N and C–C cross-coupling reactivity." Canadian Journal of Chemistry 96, no. 6 (June 2018): 578–86. http://dx.doi.org/10.1139/cjc-2017-0749.

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The competitive catalytic screening of 18 known and newly prepared Mor-DalPhos ligand variants in the palladium-catalyzed cross-coupling of chlorobenzene with aniline, octylamine, morpholine, indole, ammonia, or acetone is presented, including ligands derived from the new secondary phosphine HP(Me2Ad)2 (Me2Ad = 3,5-dimethyladamantyl). Although triarylphosphine ancillary ligand variants performed poorly in these test reactions, ligands featuring either PAd2 or P(Me2Ad)2 donors (Ad = 1-adamantyl) gave rise to superior catalytic performance. Multiple Mor-DalPhos variants proved effective in cross-couplings involving aniline, octylamine, or morpholine; conversely, only a smaller subset of ligands proved useful in related cross-couplings of indole, ammonia, or acetone. In the case of the N-arylation of indole, a Mor-DalPhos ligand variant featuring ortho-disposed PAd2 and dimethylmorpholino donor fragments (L13) proved superior to all other ligands surveyed, including the parent ligand Mor-DalPhos (L5). Conversely, L5 was found to be superior to all other ligands in the palladium-catalyzed monoarylation of ammonia. Ligand L6 (i.e., the P(Me2Ad)2 variant of L5) proved superior to all other ligands in the monoarylation of acetone and, with the exception of indole N-arylation, was the most broadly useful of the Mor-DalPhos ligands surveyed herein.

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5

Butenschön, Holger. "Haloferrocenes: Syntheses and Selected Reactions." Synthesis 50, no. 19 (August 22, 2018): 3787–808. http://dx.doi.org/10.1055/s-0037-1610210.

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Although haloferrocenes constitute important starting materials for many ferrocene-derived products with importance in a variety of fields such as materials science, medicinal chemistry and catalysis, only relatively few haloferrocenes out of the large number of possible examples have been prepared so far. The first part of this review summarizes the syntheses of all the homo- and heterohaloferrocenes known up to date. The second part summarizes typical reactions of haloferrocenes, namely lithiation followed by trapping with an electrophile, copper-mediated halogen substitution, coupling with formation of diferrocenyl derivatives, ortho-lithiation followed by trapping with an electrophile, palladium-catalyzed coupling reactions and finally miscellaneous reactions.1 Introduction2 Homohaloferrocenes2.1 Fluoroferrocenes2.2 Chloroferrocenes2.3 Bromoferrocenes2.4 Iodoferrocenes3 Heterohaloferrocenes4 Selected Reactions of Haloferrocenes4.1 Lithiation Followed by Trapping with an Electrophile4.2 Copper-Mediated Halogen Substitution4.3 Coupling with Formation of Diferrocenyl Derivatives4.4 ortho-Lithiation of Haloferrocenes4.5 Palladium-Catalyzed Reactions of Haloferrocenes4.6 Miscellaneous Reactions of Haloferrocenes5 Conclusions

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6

Blessley, George, Patrick Holden, Matthew Walker, John M. Brown, and Véronique Gouverneur. "Palladium-Catalyzed Substitution and Cross-Coupling of Benzylic Fluorides." Organic Letters 14, no. 11 (May 18, 2012): 2754–57. http://dx.doi.org/10.1021/ol300977f.

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7

Le Bras, Jean, and Jacques Muzart. "Carbonylated Indoles from PdII-Catalyzed Intermolecular Reactions of Indolyl Cores." Synthesis 51, no. 15 (May 2, 2019): 2871–90. http://dx.doi.org/10.1055/s-0037-1611478.

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This review summarizes palladium-catalyzed carbonylation, transmetalation, and cross-coupling reactions that lead to carbonylated indoles from indoles and indolyl compounds. Special attention is drawn to procedures involving the C(sp2)–H substitution of free (NH)-indoles or (N-substituted)-indoles. Proposed mechanisms are described with, in some cases, personal comments.1 Introduction2 Carbonylative Reactions2.1 Indolyl Halides as Starting Substrates2.2 Indolyl Iodides as Intermediates2.3 Indolylborates as Intermediates2.4 C(sp2)–H Reactions2.4.1 Carboxylation2.4.2 Carbonylative Alkoxylation2.4.3 Carbonylative Arylation2.4.4 Carbonylative Alkenylation2.4.5 Carbonylative Alkylation2.4.6 Double Carbonylation3 Cross-Coupling of Stannyl- or Mercurioindoles4 Cross-Coupling of Indoles4.1 Aldehydes4.2 Alcohols4.3 α-Diketones4.4 α-Oxo Esters4.5 α-Oxocarboxylic Acids4.6 Nitriles4.7 Isocyanides4.8 Isothiocyanates and Isocyanates4.9 α-Aminocarbonyl Compounds4.10 Vinyl Ethers or Vinyl Amides4.11 Toluene and Substituted Toluenes4.12 Bromodichloromethane5 Conclusion

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8

Mathias, Fanny, Youssef Kabri, Maxime Crozet, and Patrice Vanelle. "Efficient Access to Original 6-Substituted 5-Nitro-2,3-dihydroimidazo[2,1-b]oxazoles." Synthesis 49, no. 12 (April 4, 2017): 2775–85. http://dx.doi.org/10.1055/s-0036-1588984.

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A one-pot sequential intramolecular cyclization and Suzuki–Miyaura or Sonogashira reaction under microwave irradiation are reported in the 5-nitro-2,3-dihydroimidazo[2,1-b]oxazole series. The intramolecular cyclization of 1-(2,4-dibromo-5-nitro-1H-imidazol-1-yl)propan-2-ol between the hydroxyethyl group and the bromine atom at the 2-position is carried out first, followed by optimization and generalization of the Suzuki–Miyaura and Sonogashira cross-coupling reactions of the bromine atom at the 4-position. The various boronic acids and alkynyl derivatives used to perform these palladium-catalyzed cross-coupling reactions allowed to substitute the 6-position of 5-nitro-2,3-dihydroimidazo[2,1-b]oxazole compounds.

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9

Blessley, George, Patrick Holden, Matthew Walker, John M. Brown, and Veronique Gouverneur. "ChemInform Abstract: Palladium-Catalyzed Substitution and Cross-Coupling of Benzylic Fluorides." ChemInform 43, no. 40 (September 7, 2012): no. http://dx.doi.org/10.1002/chin.201240025.

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10

Kranke, Birgit, and Horst Kunz. "Stereoselective synthesis of chiral piperidine derivatives employing arabinopyranosylamine as the carbohydrate auxiliary." Canadian Journal of Chemistry 84, no. 4 (April 1, 2006): 625–41. http://dx.doi.org/10.1139/v06-060.

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Stereoselective synthesis of 2-substituted dehydropiperidinones and their further transformation to variously disubstituted piperidine derivatives was achieved employing D-arabinopyranosylamine as the stereodifferentiating carbohydrate auxiliary. A domino MannichMichael reaction of 1-methoxy-3-(trimethylsiloxy)butadiene (Danishefsky's diene) with O-pivaloylated arbinosylaldimines furnished N-arabinosyl dehydropiperidinones in high diastereoselectivity. Subsequent conjugate cuprate addition gave 2,6-cis-substituted piperidinones, while enolate alkylation furnished 2,3-trans-substituted dehydropiperidinones. Electrophilic substitution at the enamine structure afforded 5-nitro- and 5-halogen dehydropiperidinones of which the latter were applied in palladium-catalyzed coupling reactions. The absolute configuration of the obtained products was proven by NMR and X-ray structure analysis as well as by syntheses of the alkaloids (+)-coniine and (+)-dihydropinidine.Key words: piperidine alkaloids, carbohydrate auxiliary, domino MannichMichael reaction, conjugate cuprate and hydride addition, electrophilic substitution of enamines.

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11

Beletskaya, Irina, Anton Abel, Alexei Averin, Alexei Buryak, Evgenii Savelyev, Boris Orlinson, and Ivan Novakov. "The Palladium-Catalyzed Heteroarylation of Adamantylalkyl Amines with Dihalogenopyridines: Scope and Limitations." Synthesis 49, no. 22 (August 7, 2017): 5067–80. http://dx.doi.org/10.1055/s-0036-1590860.

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Palladium-catalyzed heteroarylation of adamantylalkyl amines characterized by different steric hindrances at the amino group was carried out using 2,3-, 2,5-, 2,6-, and 3,5-dihalogenopyridines. The dependence of the results of the coupling on the nature of the halogen atoms (bromine, chlorine), their position in the pyridine ring, and on the structure of adamantylalkyl amines was investigated. The application of dichloropyridines or bromochloropyridines was shown to be advantageous over the use dibromopyridines in many cases. Selective substitution of bromine atom in positions 3 and 5 in the presence of chlorine atom in position 2 of the pyridine ring was observed. The possibility of N,N-diheteroarylation of adamantane-containing amines with 2,5-dihalogenopyridines was shown, and diamination of 2,6- and 3,5-dihalogenopyridines was demonstrated.

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12

Lassagne, Frédéric, Timothy Langlais, Elsa Caytan, Emmanuelle Limanton, Ludovic Paquin, Manon Boullard, Coline Courtel, et al. "From Quinoxaline, Pyrido[2,3-b]pyrazine and Pyrido[3,4-b]pyrazine to Pyrazino-Fused Carbazoles and Carbolines." Molecules 23, no. 11 (November 13, 2018): 2961. http://dx.doi.org/10.3390/molecules23112961.

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2,3-Diphenylated quinoxaline, pyrido[2,3-b]pyrazine and 8-bromopyrido[3,4-b]pyrazine were halogenated in deprotometalation-trapping reactions using mixed 2,2,6,6-tetramethyl piperidino-based lithium-zinc combinations in tetrahydrofuran. The 2,3-diphenylated 5-iodo- quinoxaline, 8-iodopyrido[2,3-b]pyrazine and 8-bromo-7-iodopyrido[3,4-b]pyrazine thus obtained were subjected to palladium-catalyzed couplings with arylboronic acids or anilines, and possible subsequent cyclizations to afford the corresponding pyrazino[2,3-a]carbazole, pyrazino[2′,3′:5,6] pyrido[4,3-b]indole and pyrazino[2′,3′:4,5]pyrido[2,3-d]indole, respectively. 8-Iodopyrido[2,3-b] pyrazine was subjected either to a copper-catalyzed C-N bond formation with azoles, or to direct substitution to introduce alkylamino, benzylamino, hydrazine and aryloxy groups at the 8 position. The 8-hydrazino product was converted into aryl hydrazones. Most of the compounds were evaluated for their biological properties (antiproliferative activity in A2058 melanoma cells and disease-relevant kinase inhibition).

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13

Tsukada, Naofumi, Tsubasa Abe, and Yoshio Inoue. "Formation ofcine-Substitution Products in theSuzukiMiyauraCross-Coupling Reaction Catalyzed by Dinuclear Palladium Complexes." Helvetica Chimica Acta 96, no. 6 (June 2013): 1093–102. http://dx.doi.org/10.1002/hlca.201200454.

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14

Echavarren, Antonio M., Óscar de Frutos, Nuria Tamayo, Pedro Noheda, and Paloma Calle. "Palladium-Catalyzed Coupling of Naphthoquinone Triflates with Stannanes. Unprecedented Nucleophilic Aromatic Substitution on a Hydroxynaphthoquinone Triflate." Journal of Organic Chemistry 62, no. 13 (June 1997): 4524–27. http://dx.doi.org/10.1021/jo9621027.

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15

MacLean, Mark A., Craig A. Wheaton, and Mark Stradiotto. "Developing backbone-modified Mor-DalPhos ligand variants for use in palladium-catalyzed C–N and C–C cross-coupling." Canadian Journal of Chemistry 96, no. 7 (July 2018): 712–21. http://dx.doi.org/10.1139/cjc-2017-0671.

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The present contribution describes the systematic structural diversification of the κ2-P,N DalPhos ligand family in an effort to improve catalytic efficiency in the monoarylation of ammonia and acetone. The study is focused primarily on modifying the backbone phenylene linker, while retaining the same bite angle and steric bulk as the Mor-DalPhos ligand through the use of P(1-Ad)2 and morpholine donors. Eight new variants of Mor-DalPhos were prepared; two of these feature a pyridine linker (L1, L2), and five others feature either electron-donating (L3, L4) or electron-withdrawing (L5–L7) substituents on the phenylene linker. Additionally, thiomorpholino substitution (L8) was performed to investigate the effects of a possible tridentate coordination mode. Precatalyst complexes of the general formula LPd(cinnamyl)Cl were prepared and characterized in both solution and solid state. Solution studies demonstrated a significant degree of lability in the Pd–N bond, whereby dynamic behavior is seen to be dependent on the nature of the ligand backbone. The utility of these new ligands in the palladium-catalyzed monoarylation of ammonia or acetone was then surveyed. Notably, pyridine-derived ligand variants (L1, L2) were observed to out-perform parent Mor-DalPhos in the latter transformations.

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16

Chmovzh, Timofey N., Daria A. Alekhina, Timofey A. Kudryashev, Rinat R. Aysin, Alexander A. Korlyukov, and Oleg A. Rakitin. "Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) and Its Bromo Derivatives: Molecular Structure and Reactivity." International Journal of Molecular Sciences 24, no. 10 (May 16, 2023): 8835. http://dx.doi.org/10.3390/ijms24108835.

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Benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) (isoBBT) is a new electron-withdrawing building block that can be used to obtain potentially interesting compounds for the synthesis of OLEDs and organic solar cells components. The electronic structure and delocalization in benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole), 4-bromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole), and 4,8-dibromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) were studied using X-ray diffraction analysis and ab initio calculations by EDDB and GIMIC methods and were compared to the corresponding properties of benzo[1,2-c:4,5-c′]bis[1,2,5]thiadiazole (BBT). Calculations at a high level of theory showed that the electron affinity, which determines electron deficiency, of isoBBT was significantly smaller than that of BBT (1.09 vs. 1.90 eV). Incorporation of bromine atoms improves the electrical deficiency of bromobenzo-bis-thiadiazoles nearly without affecting aromaticity, which increases the reactivity of these compounds in aromatic nucleophilic substitution reactions and, on the other hand, does not reduce the ability to undergo cross-coupling reactions. 4-Bromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) is an attractive object for the synthesis of monosubstituted isoBBT compounds. The goal to find conditions for the selective substitution of hydrogen or bromine atoms at position 4 in order to obtain compounds containing a (het)aryl group in this position and to use the remaining unsubstituted hydrogen or bromine atoms to obtain unsymmetrically substituted isoBBT derivatives, potentially interesting compounds for organic photovoltaic components, was not set before. Nucleophilic aromatic and cross-coupling reactions, along with palladium-catalyzed C-H direct arylation reactions for 4-bromobenzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole), were studied and selective conditions for the synthesis of monoarylated derivatives were found. The observed features of the structure and reactivity of isoBBT derivatives may be useful for building organic semiconductor-based devices.

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17

ECHAVARREN, A. M., O. DE FRUTOS, N. TAMAYO, P. NOHEDA, and P. CALLE. "ChemInform Abstract: Palladium-Catalyzed Coupling of Naphthoquinone Triflates with Stannanes. Unprecedented Nucleophilic Aromatic Substitution on a Hydroxynaphthoquinone Triflate." ChemInform 28, no. 47 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199747112.

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18

Tsukada, Naofumi, Tsubasa Abe, and Yoshio Inoue. "ChemInform Abstract: Formation of cine-Substitution Products in the Suzuki-Miyaura Cross-Coupling Reaction Catalyzed by Dinuclear Palladium Complexes." ChemInform 44, no. 45 (October 14, 2013): no. http://dx.doi.org/10.1002/chin.201345085.

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19

Böttcher, Benjamin, Volker Schmidts, Jevgenij A Raskatov, and Christina M Thiele. "Determination of the Conformation of the Key Intermediate in an Enantioselective Palladium-Catalyzed Allylic Substitution from Residual Dipolar Couplings." Angewandte Chemie International Edition 49, no. 1 (November 26, 2009): 205–9. http://dx.doi.org/10.1002/anie.200903649.

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20

Kim, Byeong-Seon, Mahmud M. Hussain, Nusrah Hussain, and Patrick J. Walsh. "Palladium-Catalyzed Chemoselective Allylic Substitution, Suzuki-Miyaura Cross-Coupling, and Allene Formation of Bifunctional 2-B(pin)-Substituted Allylic Acetate Derivatives." Chemistry - A European Journal 20, no. 37 (July 30, 2014): 11726–39. http://dx.doi.org/10.1002/chem.201402353.

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21

Arcadi, Antonio, Marco Chiarini, Fabio Marinelli, Zoltan Berente, and Laszlo Kollar. "ChemInform Abstract: Palladium-Catalyzed Vinylic Substitution of Aryl/Vinyl Iodides and Triflates with α-Methylene-γ-butyrolactone - An Application to the Synthesis of 3-Alkyl-γ-butyrolactones Through Combined Palladium-Catalyzed Coupling/Hydrogenation Re." ChemInform 33, no. 13 (May 22, 2010): no. http://dx.doi.org/10.1002/chin.200213119.

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22

Kim, Byeong-Seon, Mahmud M. Hussain, Nusrah Hussain, and Patrick J. Walsh. "ChemInform Abstract: Palladium-Catalyzed Chemoselective Allylic Substitution, Suzuki-Miyaura Cross-Coupling, and Allene Formation of Bifunctional 2-B(pin)-Substituted Allylic Acetate Derivatives." ChemInform 46, no. 10 (February 19, 2015): no. http://dx.doi.org/10.1002/chin.201510054.

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23

Verbitskiy, Egor V., Ekaterina M. Cheprakova, Ekaterina F. Zhilina, Mikhail I. Kodess, Marina A. Ezhikova, Marina G. Pervova, Pavel A. Slepukhin, et al. "Microwave-assisted palladium-catalyzed C–C coupling versus nucleophilic aromatic substitution of hydrogen (S N H ) in 5-bromopyrimidine by action of bithiophene and its analogues." Tetrahedron 69, no. 25 (June 2013): 5164–72. http://dx.doi.org/10.1016/j.tet.2013.04.062.

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24

Ma, Shengming, and Shimin Zhao. "ChemInform Abstract: Reverse of Regioselectivity in Intramolecular Nucleophilic Substitution of π-Allyl Palladium Species. Highly Selective Formation of Vinylic Cyclopropanes via the Pd(0)-Catalyzed Coupling-Cyclization Reaction of Organic Iodides with 2-." ChemInform 31, no. 45 (November 7, 2000): no. http://dx.doi.org/10.1002/chin.200045084.

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25

Ma, Shengming, and Shimin Zhao. "Reverse of Regioselectivity in Intramolecular Nucleophilic Substitution of π-Allyl Palladium Species. Highly Selective Formation of Vinylic Cyclopropanes via the Pd(0)-Catalyzed Coupling−Cyclization Reaction of Organic Iodides with 2-(2‘,3‘-Dienyl)malonates." Organic Letters 2, no. 16 (August 2000): 2495–97. http://dx.doi.org/10.1021/ol006165u.

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26

Wade Wolfe, Michael M., Shuo Guo, Lucy S. Yu, Trenton R. Vogel, Joseph W. Tucker, and Nathaniel K. Szymczak. "Nucleophilic strategies to construct –CF₂– linkages using borazine-CF₂Ar reagents." Chemical Communications, 2022. http://dx.doi.org/10.1039/d2cc01938h.

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Using nucleophilic, boron-based –CF2Ar reagents, we demonstrate three methods to form C–CF bonds: (1) nucleophilic aromatic substitution, (2) palladium catalyzed cross-coupling, and (3) nucleophilic substitution.

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27

Negishi, Ei-ichi, and Yves Dumond. "Palladium-Catalyzed Cross-Coupling Substitution." ChemInform 34, no. 33 (August 19, 2003). http://dx.doi.org/10.1002/chin.200333280.

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28

Zhu, Yulei, Yaxin Zeng, Zhong Tao Jiang, and Ying Xia. "Recent Advances on Transition-Metal Catalyzed Cross-Coupling Reactions of Gem-Difluorinated Cyclopropanes." Synlett, July 28, 2022. http://dx.doi.org/10.1055/a-1912-3059.

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As a special class of cyclopropanes, gem-difluorinated cyclopropanes have many fascinating properties due to the gem-difluoro substitution, and thus their reactions have received much attention from the synthetic community. Recently, gem-difluorinated cyclopropanes have gradually emerged as a type of novel and unique fluorinated allylic synthon in cross-coupling reactions for the synthesis of monofluoroalkenes. Here, we briefly summarize recent advances on transition-metal catalyzed reactions of gem-difluorinated cyclopropanes. 1. Introduction 2. Palladium catalyzed reactions with linear selectivity 3. Palladium catalyzed reactions with branched selectivity 4. Other metal catalyzed reactions 5. Conclusions

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29

Peschtrich, Sebastian, Roland Schoch, Dirk Kuckling, and Jan Henry Hakan Paradies. "A Comparative Kinetic and Computational Investigation of the Carbon‐Sulfur Cross Coupling of Potassium Thioacetate and 2‐Bromo Thiophene Using Palladium/Bisphosphine Complexes." European Journal of Organic Chemistry, January 25, 2024. http://dx.doi.org/10.1002/ejoc.202301207.

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We conducted an investigation into the palladium‐catalyzed carbon‐sulfur cross‐coupling reaction involving a 2‐bromothiophene derivative and potassium thioacetate as a substitute for hydrogen sulfide. This investigation utilized kinetic and computational methods. We synthesized two palladium complexes supported by the bisphosphane ligands bis(diphenylphosphino)ferrocene (DPPF) and bis(diisopropylphosphino)ferrocene (DiPPF), as well as their tentative intermediates in the catalytic cycle. Reaction rates were measured and then compared to computational predictions.

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30

Kaur, Parmjeet, and Vikas Tyagi. "Design and preparation of novel bifunctional nanobiohybrid catalyst by combining palladium and α‐amylase enzyme: Application in the one‐pot chemoenzymatic catalysis." ChemNanoMat, October 25, 2023. http://dx.doi.org/10.1002/cnma.202300441.

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Chemoenzymatic approach which combines chemical and bio‐catalyst has proven very useful in synthetic chemistry, however, mutual deactivation of chemical and bio‐catalyst when employed in the same pot is still a challenge. In this context, the development of nanobiohybrid catalysts has played an important role and overcome the issue of mutual deactivation between catalysts to a certain extent. Herein, we design and synthesized a novel heterogeneous nanobiohybrid catalyst comprising palladium nanoparticles and α‐amylase from Aspergillus oryzae immobilized onto halloysite nanotubes as a solid heterogeneous support. Further, the wider applicability of the developed nanobiohybrid catalyst is revealed in the one‐pot chemoenzymatic synthesis of functionalized biphenyls and bis(indolyl)methanes which consist of Pd‐catalyzed Suzuki‐Miyaura coupling and α‐amylase mediated aza‐Michael addition or electrophilic substitution reactions respectively. Further, the robustness and generality of the developed one‐pot chemoenzymatic synthesis are demonstrated by incorporating different substitutions at the starting materials and obtaining the corresponding products in moderate to good yields.

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31

Paoli-Lombardo, Romain, Nicolas Primas, Sandra Bourgeade-Delmas, Alix Sournia-Saquet, Caroline Castera-Ducros, Inès Jacquet, Pierre Verhaeghe, Pascal Rathelot, and Patrice Vanelle. "Synthesis of new 5- or 7-substituted 3-nitroimidazo[1,2-a]pyridine derivatives using SNAr and palladium-catalyzed reactions to explore antiparasitic structure-activity relationships." Synthesis, December 19, 2023. http://dx.doi.org/10.1055/a-2232-8113.

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To study the antikinetoplastid structure-activity relationships in 3-nitroimidazo[1,2-a]pyridine series, we explored the substitution of positions 5 and 7 of the scaffold, developing nucleophilic aromatic substitution reactions and pallado-catalyzed Suzuki-Miyaura, Sonogashira and Buchwald-Hartwig cross-coupling reactions which had never been reported at these positions in this series. Thirty-three original compounds were obtained in 4 steps from 2-amino-bromopyridines, allowing a better definition of the antiparasitic pharmacophore.

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32

Pekbelgin Karaoğlu, Hande. "Effect of Direct Alkyne Substitution on the Photophysical Properties of Two Novel Octasubstituted Zinc Phthalocyanines." ChemistryOpen, January 26, 2024. http://dx.doi.org/10.1002/open.202300295.

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AbstractThe synthesis of two novel phthalonitrile derivatives (3–4) bearing ethynylcyclohex‐1‐ene and ethynylcyclohexane groups and two peripherally octa substituted zinc (II) phthalocyanines (5–6) were prepared. The synthesis of phthalonitrile derivatives was performed with Sonagashira coupling reaction by using palladium‐catalyzed. The newly synthesized compounds were characterized by using FT‐IR, NMR, mass, and UV‐Vis absorption spectroscopy techniques. Aggregation studies of 5 and 6 were performed in various organic solvents and different concentrations in tetrahydrofuran (THF). The photophysical studies of the Pcs were performed in THF to determine the effect of the alkyne groups on the fluorescence of the Pc ring. Substances showing fluorescence properties can be used in practical applications such as to create an image in microscopy. Fluorescence quantum yield (ΦF) and fluorescence lifetime (τF) of 5–6 were calculated. The fluorescence quenching studies of 5–6 were performed by adding the different concentrations of 1,4‐benzoquinone (BQ) to a constant concentration of the Pcs in THF and it was found that benzoquinone was an effective quencher. The values of the Stern‐Volmer constant (Ksv) and quenching constant (kq) of zinc phthalocyanines (5–6) were examined. All obtained results were compared with each other and with unsubstituted zinc Pc compound used as a reference.

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33

Negishi, Ei-ichi. "Palladium-Catalyzed Cross-Coupling Involving β-hetero-Substituted Compounds. Palladium-Catalyzed α-Substitution Reactions of Enolates and Related Derivatives Other than the Tsuji—Trost Allylation Reaction." ChemInform 34, no. 33 (August 19, 2003). http://dx.doi.org/10.1002/chin.200333282.

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34

Willis, Michael C., Jay Chauhan, and William G. Whittingham. "A New Reactivity Pattern for Vinyl Bromides: cine-Substitution via Palladium-Catalyzed C—N Coupling/Michael Addition Reactions." ChemInform 37, no. 2 (January 10, 2006). http://dx.doi.org/10.1002/chin.200602084.

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Chang, Yu-Hsiang, Weijia Shen, Jonathan Z. Shezaf, Eliezer Ortiz, and Michael J. Krische. "Palladium(I)-Iodide-Catalyzed Deoxygenative Heck Reaction of Vinyl Triflates: A Formate-Mediated Cross-Electrophile Reductive Coupling with cine-Substitution." Journal of the American Chemical Society, October 16, 2023. http://dx.doi.org/10.1021/jacs.3c09876.

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36

Shcherbakov, Konstantin V., Mariya A. Panova, Yanina V. Burgart, Ekaterina O. Sinegubova, Iana R. Orshanskaya, Vladimir V. Zarubaev, Natalia A. Gerasimova, Natalia P. Evstigneeva, and Victor I. Saloutin. "Alternative Functionalization of 2‐(3,4‐Dihalophenyl)‐4 H ‐chromen‐4‐ones via Metal‐Free Nucleophilic Aromatic Fluorine Substitution and Palladium‐Catalyzed Cross‐Coupling Reactions." ChemistrySelect 7, no. 33 (September 2, 2022). http://dx.doi.org/10.1002/slct.202201775.

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