Relevant bibliographies by topics / Directed Ortho Metalation

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Academic literature on the topic 'Directed Ortho Metalation'

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Published: 4 June 2021
Last updated: 1 February 2022

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Journal articles on the topic "Directed Ortho Metalation"

1

Slocum, D. W., D. Reed, F. Jackson, and C. Friesen. "Media effects in directed ortho metalation." Journal of Organometallic Chemistry 512, no. 1-2 (April 1996): 265–67. http://dx.doi.org/10.1016/0022-328x(95)05990-7.

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2

Talko, Alicja, Damian Antoniak, and Michał Barbasiewicz. "Directed ortho-Metalation of Arenesulfonyl Fluorides and Aryl Fluorosulfates." Synthesis 51, no. 11 (April 11, 2019): 2278–86. http://dx.doi.org/10.1055/s-0037-1610877.

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Studies on directed ortho-metalation (DoM) of arenesulfonyl fluorides (ArSO2F) with in situ electrophile trapping are presented. Under optimized conditions (LDA, THF, –78 °C), a series of model substrates was mono- and difunctionalized with trimethylsilyl chloride in good yields. The synthetic results reveal powerful directing character of the SO2F group, being ahead of bromine and methoxy substituents. Under the same metalation conditions, aryl fluorosulfates (ArOSO2F) display fragmentation to arynes and migration of the SO2F group to the ortho position (anionic thia-Fries rearrangement).
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3

Snieckus, Victor, and Claude Quesnelle. "The Directed ortho Metalation (DoM)–Cross-Coupling Connection: Synthesis of Polyfunctional Biaryls." Synthesis 50, no. 22 (October 5, 2018): 4413–28. http://dx.doi.org/10.1055/s-0037-1610273.

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A comparative evaluation of the combined directed ortho metalation (DoM)–Suzuki–Miyaura and DoM–Negishi cross-coupling reactions with aryl triflates for the synthesis of substituted biaryls is described. Both ortho-zinc and ortho-boron aryl directed metalation group (DMG = CON(i-Pr)2, OCONEt2, OMOM, NHBoc) substrates were evaluated. The superiority of the DoM–Negishi over the DoM–Suzuki–Miyaura reaction in operational convenience and mild reaction conditions is noted. Orthogonal Negishi and Suzuki–Miyaura with Corriu–Kumada reactions for the synthesis of a teraryl derivative is also reported.
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Laufer, Radoslaw, Ulrich Veith, Nicholas J. Taylor, and Victor Snieckus. "(–)-Sparteine-mediated stereoselective directed ortho metalation of ferrocene diamides." Canadian Journal of Chemistry 84, no. 2 (February 1, 2006): 356–69. http://dx.doi.org/10.1139/v06-008.

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The utility of (–)-sparteine-mediated directed ortho metalation (DoM) has been investigated in stereoselective preparation of planar chiral ferrocenes derived from 1,1′-N,N,N′,N′-tetraisopropylferrocenedicarboxamide (5). In the synthesis of C2-symmetric analogs of 5, the protocol (base, solvent, and two-step DoM) was found to be crucial for obtaining high enantio- and diastereo-selectivities of the products. A variety of highly enantioenriched mono and doubly functionalized derivatives of 5 have been synthesized. The synthetic applications of these compounds as chiral ligands in asymmetric alkylation of aldehydes and asymmetric palladium-catalyzed allylic substitutions have been demonstrated.Key words: directed ortho metalation, stereoselective deprotonation, ferrocene ligands, asymmetric catalysis.
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5

Cai, Xiongwei, Stephen Brown, Peter Hodson, and Victor Snieckus. "Regiospecific synthesis of alkylphenanthrenes using a combined directed ortho and remote metalation – Suzuki–Miyaura cross coupling strategy." Canadian Journal of Chemistry 82, no. 2 (February 1, 2004): 195–205. http://dx.doi.org/10.1139/v03-179.

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Using a combined directed ortho metalation (DoM) – Suzuki–Miyaura cross coupling – directed remote metalation (DreM) approach, the alkylphenanthrenes (APs) 1-methyl- (5a), 1,7-dimethyl- (5b), 2,7-dimethyl- (5c), 7-ethyl-1-methyl- (15), and 7-tert-butyl-1-methylphenanthrenes (27) have been synthesized in four to seven steps and 21%–36% overall yields. In contrast to classical protocols, this method, which may be scaled to gram quantities, provides single isomers of APs in high purity of value as analytical standards for environmental studies. Aminocarbonylation of triflates to N,N-diethylbenzamides (9 [Formula: see text] 10) and anionic Fries rearrangement (23 [Formula: see text] 24) provide other potential links to DoM chemistry.Key words: phenanthrene, directed ortho metalation, Suzuki–Miyaura cross coupling, synthesis, polycyclic aromatic hydrocarbon, carbonylation.
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Fu, Jian-min, and Victor Snieckus. "The directed ortho metalation - palladium catalyzed cross coupling connection. A general regiospecific route to 9-phenanthrols and phenanthrenes. Exploratory further metalation." Canadian Journal of Chemistry 78, no. 6 (June 1, 2000): 905–19. http://dx.doi.org/10.1139/v00-055.

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A new general and regiospecific synthesis of 9-phenanthrols (1 +2 [Formula: see text] 3 [Formula: see text] 4, Scheme 1, Table 1) proceeding by a Directed ortho Metalation (DoM), Suzuki-Miyaura cross coupling, and a new LDA-mediated Directed remote Metalation sequence is described. The facile Pd-catalyzed hydrogenolysis of the phenanthrols 4 into the corresponding phenanthrenes 5 via their triflates 18 translates the original DoM regioselectivity also into a general synthesis of phenanthrenes (Table 2). Further DoM (19 [Formula: see text]20, 21; 24 [Formula: see text]25), cross coupling (20c [Formula: see text]23), as well as oxidation - ring contraction (4b, 4f [Formula: see text]28a, 28b) chemistry of phenanthrene derivatives is reported.Key words: 9-phenanthrols, directed ortho metalation, Suzuki cross coupling, synthesis.
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7

Llopart, Carme Cantos, Conchita Ferrer, and John A. Joule. "Lithiation of 1-arylimidazol-2(1H)-ones and 1-aryl-4,5-dihydroimidazol-2(1H)-ones." Canadian Journal of Chemistry 82, no. 11 (November 1, 2004): 1649–61. http://dx.doi.org/10.1139/v04-137.

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1-Arylimidazol-2(1H)-ones are shown to be readily lithiated, using 2 mol equiv. of n-butyllithium, on the benzene ring, ortho to the heterocycle. 1-Aryl-4,5-dihydroimidazol-2(1H)-ones also undergo metalation on the aromatic substitutuent ortho to the heterocycle, but less efficiently. 1-Aryl-3-methylimidazol-2(1H)-ones are lithiated on the heterocyclic ring and then on the benzene ring ortho to the heterocycle. No ortho-directing effect was found for 1-aryl-4,5-dihydro-3-methylimidazol-2(1H)-ones.Key words: ortho-lithation, ureas for directed ortho metalation, 1-arylimidazol-2-ones, 1-arylimidazolidin-2-ones.
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8

Cho, Inhee, Labros Meimetis, Lee Belding, Michael J. Katz, Travis Dudding, and Robert Britton. "Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis." Beilstein Journal of Organic Chemistry 7 (September 22, 2011): 1315–22. http://dx.doi.org/10.3762/bjoc.7.154.

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A variety of ortho,ortho'-disubstituted hydrobenzoin derivatives are readily accessible through a directed ortho,ortho'-dimetalation strategy in which the alcohol functions in hydrobenzoin are deprotonated by n-BuLi and the resulting lithium benzyl alkoxides serve as directed metalation groups. The optimization and scope of this reaction are discussed, and the utility of this process is demonstrated in the one-pot preparation of a number of chiral diols as well as a short synthesis of the chiral ligand Vivol.
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9

Tsukazaki, Masao, and Victor Snieckus. "Directed ortho metalation – radical-induced cyclization synthetic connections. A route to highly substituted benzofurans." Canadian Journal of Chemistry 70, no. 5 (May 1, 1992): 1486–91. http://dx.doi.org/10.1139/v92-184.

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The synthesis of benzofurans 20a–c, which constitute analogues of 5-lipoxygenase inhibitors 4, is described. The route, representing a potential general method for benzofuran construction, proceeds from phenyl carbamate 11 and involves key directed ortho metalation (11 → 12), anionic ortho-Fries rearrangement (12 → 13a), and radical-induced cyclization (17a–c → 18a–c) steps.
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10

Miah, M. A. Jalil, Mukund P. Sibi, S. Chattopadhyay, Oluwole B. Familoni, and Victor Snieckus. "Directed ortho -Metalation of O -Aryl N ,N -Dialkylcarbamates: Methodology, Anionic ortho -Fries Rearrangement, and Lateral Metalation." European Journal of Organic Chemistry 2018, no. 4 (December 5, 2017): 440–46. http://dx.doi.org/10.1002/ejoc.201701142.

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Dissertations / Theses on the topic "Directed Ortho Metalation"

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Timmons, Michael. "Directed Ortho-Metalation of Dimethylarylamines." TopSCHOLAR®, 2002. http://digitalcommons.wku.edu/theses/641.

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Site-specific product(s) from the reaction of benzene derivatives with various reagents is a need of researchers at numerous laboratories, particularly those in the pharmaceutical industry. Such derivatives can be synthesized directly, i.e., by substitution of a proton, using either of two procedures: electrophilic aromatic substitution (EAS) or directed ortho-metalation (DoM). Directed ortho-metalation (DoM) is an alternative aromatic substitution process initiated by organolithium reagents which provides regiospecific substitution exclusively at the ortho- position (equation). The focus of this study is to find hydrocarbon media that will permit the maximum extent of metalation of several dimethylarylamines. The dimethylamine-containing substituents constitute directing metalation groups (DMG's) for the various aryl systems investigated. Maximization of the extents of ortho-lithiation of dimethylaniline [DMG = - N(CH3)2] and dimethylbenzylamine [DMG = -CH2N(CH3)2] have now been achieved using novel combinations of solvent, temperature and increments of catalyst. Studies of substituted dimethylanilines and dimethylbenzylamines containing a second DMG have yielded mixed results. Both metalation condition parameters as well as certain mechanistic aspects are altered by inclusion of a second DMG into these two parent systems.
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Woosley, Barry. "Directed ortho Metalation in Hydrocarbon Solvents: Opposing Pi-Resonance Effects." TopSCHOLAR®, 2004. http://digitalcommons.wku.edu/theses/539.

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Hydrocarbon solvents are known to be unreactive toward organolithium reagents and do not typically support ortho-metalation reactions without the aid of a promoter. An exception would be an arene substrate having the capability to bidentate complex to the reactive alkyllithium dimer, which enables ortho-metalation to occur in high yields. A second, more limiting exception, would be that the arene substrate possesses localized lone pairs of electrons, as is the case when the directed ortho metalating group (DMG) is located in the benzyl position. The work reported here centers upon developing a third and larger class of arene substrates that are exceptions to the general rule that metalation in hydrocarbon solvents requires the use of added promoter. When an arene is either 1,2- or 1,4- disubstituted with electron donating DMGs, the lone pairs of electrons on each of the DMG groups are more localized than is the case for a monosubstituted arene. The effect of localization allows the arene to complex more efficiently and therefore metalate. This localization effect we term the Opposing Pi Resonance Effect.
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Cai, Xiongwei. "Regiospecific synthesis of alkylphenanthrenes using a combined directed ortho metalation, DoM, (Suzuki-Miyaura cross coupling), directed remote metalation, DreM, methodology." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2001. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp05/MQ63276.pdf.

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4

Friesen, Carl. "Directed Ortho-Metalation of the Three Methyl Anisoles in Various Media." TopSCHOLAR®, 1996. http://digitalcommons.wku.edu/theses/870.

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Directed ortho-metalation (DoM) is a very useful alternative to electrophillic aromatic substitution (EAS) for the synthesis of substituted aromatic compounds. DoM is highly regiospecific providing metalation chiefly in the ortho-position. However, lateral (a-) metalation of an alkyl side-chain and ortho-metalation of a second ortho-position can compete. Investigation of the three methylanisoles was therefore undertaken to determine the interplay between these factors and to discover metalation conditions to achieve selectivity. This goal was uniquely achieved for p-methylanisole where conditions were discovered which allowed > 85% ortho-metalation as determined by GC analysis with virturally no competing lateral metalation. Three derivitives of this ortho-lithio intermediate were prepared, each in > 75% yield. Metalation conditions were found that permitted significant descrimination between 2- and 6- position metalation of m-methylanisole. Metalation conditions were also found that permitted regiospecific a-metalation of o-methylanisole.
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Macklin, Todd Kristopher. "The development of sulfamates as latent directed metalation groups. Total synthesis of schumanniophytine. Divergent synthesis of substituted chromone 3- and 8-carboxamides." Thesis, Kingston, Ont. : [s.n.], 2007. http://hdl.handle.net/1974/925.

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Milburn, Claire Louise Maud Jackson. "The directed ortho metalation reaction of aryl O-carbamates on solid support." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2001. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp05/MQ63340.pdf.

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Kendall, Christopher Nicholas Owen. "The directed ortho metalation - Suzuki-Miyaura cross-coupling connection, towards the total synthesis of dehydrorabelomycin." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2000. http://www.collectionscanada.ca/obj/s4/f2/dsk1/tape3/PQDD_0020/MQ54462.pdf.

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8

Lai, Ping-Shan. "Directed ortho metalation-boronation Suzuki-Miyaura cross coupling leading to synthesis of azafluorenol core liquid crystals." Thesis, Kingston, Ont. : [s.n.], 2007. http://hdl.handle.net/1974/511.

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9

Chauder, Brian Andrew. "Combined directed ortho metalation-transition metal catalyzed coupling reactions for the synthesis of chromenes, ergot alkaloids, and biaryl macrocycles." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2001. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp04/NQ63410.pdf.

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10

Onuska, Nicholas Paul Ralph. "Studies Towards the Synthesis of 2,5-Disubstituted-3-Fluorothiophenes Using a Directed Ortho-Metalation/Nickel-Catalyzed Cross-Coupling Approach." Kent State University Honors College / OhioLINK, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=ksuhonors1460652408.

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Book chapters on the topic "Directed Ortho Metalation"

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Taber, Douglass F. "The Kuwahara Synthesis of Paspalinine." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0102.

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The hexacyclic indole diterpenoid paspalinine 3, produced by the ergot Claviceps paspali, induces tremors in domestic animals that graze on pasture grass infected by that fungus. Shigefumi Kuwahara of Tohoku University envisioned (Angew. Chem. Int. Ed. 2012, 51, 12833) assembly of the tetracyclic nucleus of 3 by the oxidative cyclization of 1 to 2. The challenge, then, was the assembly of the angularly substituted trans–anti-trans-6-6-5 alicyclic nucleus of 1. The synthesis began with the Wieland-Miescher ketone 4, which is available commercially in enantiomerically pure form. Exposure to ethylene glycol under acidic conditions converted 4 to the known monoketal 5. The alkylation with 6 followed by selective hydrolysis gave 7 as an inconsequential mixture of diastereomers. Exposure to base effected both equilibration to the more stable equatorial diastereomer and cyclization to give the enone 8. There was still the problem of the introduction of the axial angular methyl group. This was solved by selective reduction of 8 to the endo alcohol. Hydroxyl-directed Simmons-Smith cyclopropanation followed by oxidation gave 9. The enolate resulting from the dissolving metal reduction of 9 was trapped with Comins reagent to generate the enol triflate 10. Acetanilide 11 was converted to the stannane 12 by ortho metalation following the literature protocol. Pd-mediated coupling of 12 with 10 proceeded efficiently to give 1. Oxidation with stoichiometric Pd trifluoroacetate then induced Type 5 indole formation (Tetrahedron 2011, 67, 7195). Hydrolysis and conjugation completed the synthesis of 2. To introduce the sidechain, the enone was converted to the allyl enol carbonate. Pd-mediated rearrangement converted that to the α-allyl enone, which participated in Ru-catalyzed metathesis with 14 to give 15. Asymmetric dihydroxylation proceeded with only modest diastereoselectivity, but only the desired diastereomer cyclized onto the ketone to give 16. The ketone 16 was an intermediate in Smith’s earlier synthesis. Professor Kuwahara devised an alternate end game, selenylation followed by oxidation and sigmatropic rearrangement, to install the axial OH and complete the synthesis of paspalinine 3.
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2

Taber, Douglass F. "Preparation of Substituted Benzenes: The Beaudry Synthesis of Arundamine." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0064.

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Stephen G. DiMagno of the University of Nebraska developed (Chem. Eur. J. 2015, 21, 6394) a protocol for the clean monoiodination of 1 to 2. The bromomethylation (or chloromethylation, with HCl) of a benzene derivative is straightforward with formal­dehyde and HBr. Naofumi Tsukada of Shizuoka University designed (Organometallics 2015, 34, 1191) a Cu catalyst that mediated the coupling of an alkyne with the benzyl bromide so produced, effecting net propargylation of 3 with 4 to give 5. Triazenes such as 7, versatile intermediates for organic synthesis, are usually prepared by diazotization of the corresponding aniline. Kay Severin of the Ecole Polytechnique Fédérale de Lausanne established (Angew. Chem. Int. Ed. 2015, 54, 302) an alternative route from the aryl Grignard reagent 6. Ping Lu and Yanguang Wang of Zhejiang University showed (Chem. Commun. 2015, 51, 2840) that dimethylformamide could serve as the carbon source for the conversion of 8 to the nitrile 9. Junha Jeon of the University of Texas at Arlington effected (J. Org. Chem. 2015, 80, 4661; Chem. Commun. 2015, 51, 3778) the reductive ortho silylation of 10 to give 11. Vladimir Gevorgyan of the University of Illinois at Chicago found (Angew. Chem. Int. Ed. 2015, 54, 2255) that the phenol derivative 12 could be ortho carboxylated, leading to 13. Lutz Ackermann of the Georg-August-Universität Göttingen, starting (Chem. Eur. J. 2015, 21, 8812) with the designed amide 14, effected ortho metala­tion followed by coupling, to give the methylated product 15. Tetsuya Satoh and Masahiro Miura of Osaka University used (Org. Lett. 2015, 17, 704) the dithiane of 16 to direct ortho metalation. Coupling with acrylate followed by reductive desulfu­rization led to the ester 17. Jin-Quan Yu of Scripps/La Jolla designed (Angew. Chem. Int. Ed. 2015, 54, 888) the phenylacetamide 18 to direct selective meta metalation, leading to the unsat­urated aldehyde 19. In an extension of the Catellani protocol, Guangbin Dong of the University of Texas prepared (J. Am. Chem. Soc. 2015, 137, 5887) the biphenyl 21 by net meta metalation of the benzylamine 20. Several methods for the de novo assembly of benzene derivatives have recently been put forward. Rajeev S. Menon of the Indian Institute of Chemical Technology condensed (Org. Lett. 2015, 17, 1449) the unsaturated aldehyde 22 with the sulfonyl ester 23 to give 24.
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