Relevant bibliographies by topics / C-H Direct Arylation

Contents

  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters
  4. Conference papers

Academic literature on the topic 'C-H Direct Arylation'

Author: Grafiati
Published: 4 June 2021
Last updated: 6 February 2022

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Journal articles on the topic "C-H Direct Arylation"

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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 (2017): 2523–34. http://dx.doi.org/10.1055/s-0036-1588734.

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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]
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Maiti, Debabrata, Sumon Basak, and Jyoti Prasad Biswas. "Transition-Metal-Catalyzed C–H Arylation Using Organoboron Reagents." Synthesis 53, no. 18 (2021): 3151–79. http://dx.doi.org/10.1055/a-1485-4666.

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AbstractAryl rings are ubiquitous in the core of numerous natural product and industrially important molecules and thus their facile synthesis is of major interest in the scientific community and industry. Although multiple strategies enable access to these skeletons, metal-catalyzed C–H activation is promising due to its remarkable efficiency. Commercially available organoboron reagents, a prominent arylating partner in the cross-coupling domain, have also been utilized for direct arylation. Organoborons are bench-stable, inexpensive, and readily available coupling partners that promise regio
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Wencel-Delord, Joanna, and Françoise Colobert. "Challenging Atroposelective C–H Arylation." SynOpen 04, no. 04 (2020): 107–15. http://dx.doi.org/10.1055/s-0040-1705981.

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AbstractAtropisomeric molecules are privileged scaffolds, not only as ligands for asymmetric synthesis, but also as biologically active products and advanced materials. Although very attractive from a sustainability viewpoint, the direct construction of the stereogenic axis through asymmetric C–H arylation is very challenging and consequently only a few examples have been reported. This short review summarizes these very recent results on the atropo-enantio or diastereo­selective synthesis of atropisomeric (hetero)biaryl molecules; transformations during which the Ar–Ar atropisomeric axis is f
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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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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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Abdelmalek, Fatiha, Fazia Derridj, Safia Djebbar, Jean-François Soulé та Henri Doucet. "Efficient synthesis of π-conjugated molecules incorporating fluorinated phenylene units through palladium-catalyzed iterative C(sp2)–H bond arylations". Beilstein Journal of Organic Chemistry 11 (28 жовтня 2015): 2012–20. http://dx.doi.org/10.3762/bjoc.11.218.

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We report herein a two or three step synthesis of fluorinated π-conjugated oligomers through iterative C–H bond arylations. Palladium-catalyzed desulfitative arylation of heteroarenes allowed in a first step the synthesis of fluoroaryl-heteroarene units in high yields. Then, the next steps involve direct arylation with aryl bromides catalyzed by PdCl(C3H5)(dppb) to afford triad or tetrad heteroaromatic compounds via regioselective activation of C(sp2)–H bonds.
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Patra, Tuhin, Sudip Nandi, Santosh K. Sahoo, and Debabrata Maiti. "Copper mediated decarboxylative direct C–H arylation of heteroarenes with benzoic acids." Chemical Communications 52, no. 7 (2016): 1432–35. http://dx.doi.org/10.1039/c5cc08367b.

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Copper mediated decarboxylative direct C–H arylation of 5-membered heteroarenes with aryl carboxylic acids is developed using the molecular oxygen as sole oxidant. Copper plays the dual role in decarboxylation and C–H arylation.
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Lamblin, Marc, François-Xavier Felpin, Guillaume Naturale, and Jean Dessolin. "Direct C-H Arylation of Quinones with Anilines." Synlett 23, no. 11 (2012): 1621–24. http://dx.doi.org/10.1055/s-0031-1291163.

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Ihanainen, Netta E., Esa T. T. Kumpulainen, and Ari M. P. Koskinen. "Palladium-Catalyzed Direct C-H Arylation of Dicyanobenzenes." European Journal of Organic Chemistry 2015, no. 15 (2015): 3226–29. http://dx.doi.org/10.1002/ejoc.201500288.

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To, Ching Tat, Wu Yang, and Kin Shing Chan. "Porphyrins and Phthalocyanines Catalyzed Direct CH Arylation." Chinese Journal of Chemistry 34, no. 10 (2016): 955–61. http://dx.doi.org/10.1002/cjoc.201600442.

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Sharma, Upendra, Atanu Modak, Soham Maity, Arun Maji, and Debabrata Maiti. "ChemInform Abstract: Direct Arylation via C-H Activation." ChemInform 46, no. 18 (2015): no. http://dx.doi.org/10.1002/chin.201518322.

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Dissertations / Theses on the topic "C-H Direct Arylation"

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Yagoubi, Myriam. "Synthesis of heterocycles via palladium-catalysed direct arylation." Thesis, University of Oxford, 2011. http://ora.ox.ac.uk/objects/uuid:e1206b3a-b9e8-4371-a94c-da3bc04c116e.

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Chapter 1 is a brief review on some of the recents developments in palladium-catalysed C-H functionalisation chemistry. The synthesis and functionalisation of heterocycles using these methodologies was particularly emphasised. Chapter 2 presents our efforts to identify a new catalytic system to promote the intramolecular coupling of vinyl bromides with unfunctionalised aryl C-H bonds for the formation of benzofurans. Dihydrobenzofurans were obtained efficiently under mild conditions in the presence of Pd(OAc)₂, X-Phos and K₂CO₃ in DMA at 80 °C and a subsequent one-pot isomerisation under acidi
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Chen, Lu. "Palladium-catalysed C-C bond construction in virtue of C-H functionalisation : direct arylation of heteroaromatics tolerant to reactive functional groups." Thesis, Rennes 1, 2013. http://www.theses.fr/2013REN1S011.

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Durant ma thèse, j'ai recherché les conditions pour l'activation / fonctionnalisation de liaisons C-H pour la construction de bi(hétéro)aryles tolérant des groupement fonctionnels réactifs tels que des silyles, des alcènes, des esters ou encore des amides. Par rapport aux protocoles de couplage classiques tels que les réactions de Suzuki, Stille ou Negishi, la fonctionalisation de liaisons C-H fournit des procédures moins coûteuses et plus écologiques si elle tolère des groupements utiles en synthèse. D'abord, nous avons observé que les thiophènes substitués par des silyles en C2 peuvent être
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Zhao, Liqin. "Palladium-catalyzed direct arylation via sp² and sp³ C-H activation of hetero(aromatics) and hydrocarbons for C-C bond formation." Thesis, Rennes 1, 2014. http://www.theses.fr/2014REN1S038/document.

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Au cours de cette thèse, nous nous sommes intéressés à l'activation de liaisons sp² et sp³ C-H catalysée par le palladium pour la préparation d'(hétéro)aryl-aryles et de biaryles. Cette méthode est considérée comme attractive pour l'environnement par rapport aux méthodes classiques, tels que Suzuki, Heck, ou Negishi. Tout d'abord, nous avons décrit que la C2-arylation directe de benzothiophènes peut être effectuée par un catalyseur du palladium en l'absence de ligand phosphine avec une grande sélectivité. Nous avons également démontré qu'il est possible d'activer les positions C2 et C5 de pyrr
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Beydoun, Kassem. "Palladium catalyzed direct arylation of heteroaromatics via C-H bond activation : a green access to fine chemicals and materials." Rennes 1, 2012. http://www.theses.fr/2012REN1S174.

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During this thesis, we were interested in the C-H bonds activation catalyzed by palladium catalysts such PdCl(C₃H₅)(dppb) and ligand-free or ligand associated Pd(OAc)₂ for the préparation of biaryls. This method is considered as cost effective and environmentally attractive compared to other types of couplings such as Suzuki, Stille, or Negishi. First we demonstrated that it is possible to apply C-H bond activation method for the direct arylation of formyl or acetyl halothiophene derivatives. The corresponding products could be further functionalized due to the presence of the halo and carbony
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Li, Haoran. "Pd-catalyzed C-H bond functionalizations of (hetero)arenes and alkenes : A one step access to poly(hetero)aromatics and styrene derivatives." Thesis, Rennes, Ecole nationale supérieure de chimie, 2020. http://www.theses.fr/2020ENCR0068.

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Afin d'expliquer le contexte de mon travail de recherche, j'ai résumé dans le premier chapitre des informations mécanistiques générales sur l'arylation des liaisons C-H catalysée par le palladium et j'ai détaillé certains travaux sur l'arylation directe en relation avec mes travaux. Mes objectifs étaient d'étudier la réactivité de nouvelles unités synthétiques permettant l'accès direct à des composés bi-(hétéro)aryls ou à des dérivés du styrène. Ensuite, dans les chapitres 2 à 6, j'ai résumé mes travaux de recherche. J'ai étudié l’arylation directes en C2 du Methoxsalen par des chlorures de be
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Skhiri, Aymen. "Réactivité des chlorures de benzènesulfonyle pour l'accès à des hétéroarènes et alcènes arylés via des réactions pallado-catalysées." Thesis, Rennes 1, 2017. http://www.theses.fr/2017REN1S080.

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Au cours de cette thèse, nous nous sommes intéressés à la synthèse d’hétérocycles arylés via l’activation de liaisons sp2 C-H d’hétéroaromatiques et à la synthèse d’alcènes arylés halo-substitués catalysée par le palladium. Les produits obtenus sont considérés comme des briques moléculaires, intéressantes pour les biochimistes, ainsi que pour la préparation de matériaux. Le système catalytique Pd(MeCN)2Cl2/Li2CO3/dioxane permet l’accès direct à une grande variété de molécules arylées à partir d’hétéroarènes ou d’alcènes et de chlorures de benzènesulfonyle. Nous avons mis au point une méthode p
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Zhu, Yingjun. "Sustainable Strategies for Site-Selective C–H Functionalizations of N-Heterocycles." Doctoral thesis, Niedersächsische Staats- und Universitätsbibliothek Göttingen, 2015. http://hdl.handle.net/11858/00-1735-0000-0022-5DDA-D.

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Schipper, Derek. "Part 1: Transition Metal Catalyzed Functionalization of Aromatic C-H Bonds / Part 2: New Methods in Enantioselective Synthesis." Thèse, Université d'Ottawa / University of Ottawa, 2011. http://hdl.handle.net/10393/20121.

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Part 1: Transition-metal-catalyzed direct transformations of aromatic C-H bonds are emerging as valuable tools in organic synthesis. These reactions are attractive because of they allow for inherently efficient construction of organic building blocks by minimizing the pre-activation of substrates. Of these processes, direct arylation has recently received much attention due to the importance of the biaryl core in medicinal and materials chemistry. Also, alkyne hydroarylation has garnered interest because it allows for the atom-economical synthesis of functionalized alkenes directly from si
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Naturale, Guillaume. "Approches radicalaires pour la fonctionnalisation directe de quinones à visée anticancereuse." Thesis, Bordeaux 1, 2012. http://www.theses.fr/2012BOR14635/document.

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Dans le cadre d’un programme de recherche dédié à la découverte de petites molécules à visée anticancéreuse, nous avons envisagé de concevoir des composés originaux dérivés de quinones. Notre premier objectif a été d’élaborer des mimes non-peptidiques de la protéine Smac, susceptibles de participer à relancer le phénomène d’apoptose, dont la structure est rigidifiée par des contraintes conformationnelles. Par ailleurs, les kinases et les phosphatases, jouant des rôles complémentaires de phosphorylation / déphosphorylation dans le cadre du contrôle du cycle cellulaire notamment, apparaissent au
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Eichhorst, Christoph. "Untersuchungen zur Synthese fluoreszenzaktiver aromatischer Polyzyklen durch Palladium-katalysierte Domino-C‒H-Aktivierungen." Doctoral thesis, Niedersächsische Staats- und Universitätsbibliothek Göttingen, 2014. http://hdl.handle.net/11858/00-1735-0000-0023-993C-7.

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Book chapters on the topic "C-H Direct Arylation"

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Fagnou, Keith. "Mechanistic Considerations in the Development and Use of Azine, Diazine and Azole N-Oxides in Palladium-Catalyzed Direct Arylation." In C-H Activation. Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/128_2009_14.

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Morin, Jean-Francois, Maxime Daigle, and Maude Desroches. "Photochemical and Direct CH Arylation Routes toward Carbon Nanomaterials." In Synthetic Methods for Conjugated Polymers and Carbon Materials. Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527695959.ch7.

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Miura, Masahiro, and Masakatsu Nomura. "Direct Arylation via Cleavage of Activated and Unactivated C-H Bonds." In Topics in Current Chemistry. Springer Berlin Heidelberg, 2002. http://dx.doi.org/10.1007/3-540-45313-x_6.

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Ackermann, Lutz, and Rubén Vicente. "Ruthenium-Catalyzed Direct Arylations Through C–H Bond Cleavages." In C-H Activation. Springer Berlin Heidelberg, 2009. http://dx.doi.org/10.1007/128_2009_9.

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Bellina, Fabio. "Recent Developments in Pd-Catalyzed Direct Arylations of Heteroarenes with Aryl Halides." In C-H Bond Activation and Catalytic Functionalization I. Springer International Publishing, 2015. http://dx.doi.org/10.1007/3418_2015_121.

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Satoh, Tetsuya, and Masahiro Miura. "Catalytic Arylation and Vinylation Reactions Directed by Anionic Oxygen Functions via Cleavage of C – H and C – C Bonds." In Topics in Organometallic Chemistry. Springer Berlin Heidelberg, 2007. http://dx.doi.org/10.1007/3418_2007_066.

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Taber, Douglass F. "Selective Functionalization of C–H Bonds." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0019.

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Jianhui Huang and Kang Zhao of Tianjin University devised (Chem. Commun. 2013, 49, 1211) a protocol for the oxidation of a terminal alkene 1 to the valuable four-carbon synthon 2. M. Christina White of the University of Illinois effected (J. Am. Chem. Soc. 2013, 135, 7831) the oxidation of the terminal alkene 3 to the enone 4. Miquel Costas of the Universitat de Girona developed (J. Org. Chem. 2013, 78, 1421; Chem. Eur. J. 2013, 19, 1908) a family of Fe catalysts for the oxidation of methylenes to ketones. Depending on the catalyst, any of the three ketones from the oxidation of 5, including 6, could be made the dominant product. Yumei Xiao and Zhaohai Qin of China Agricultural University optimized (Synthesis 2013, 45, 615) the Co-catalyzed oxidation of the methyl group of 7 to give the aldehyde 8. Thanh Binh Nguyen of CNRS Gif-sur-Yvette established (J. Am. Chem. Soc. 2013, 135, 118) a protocol (not illustrated) for the oxidation of methyl groups on heteroaromatics. Shunsuke Chiba of Nanyang Technological University cyclized (Org. Lett. 2013, 15, 212, 3214) the amidine 9 to 10, and the hydrazone 11 to 12. These cyclizations proceeded by sequential C–H abstraction followed by recombination, and so were racemizing. In contrast, the conversion of 13 to 14, developed (Science 2013, 340, 591) by Theodore A. Betley of Harvard University, proceeded with substantial reten­tion of absolute configuration. Tsutomu Katsuki of Kyushu University designed (Angew. Chem. Int. Ed. 2013, 52, 1739) a Ru catalyst that was selective for the allylic position of the E-alkene 15 to give 16. Amination was highly regioselective, and proceeded with excellent ee. Ilhyong Ryu of Osaka Prefecture University and Maurizio Fagnoni of the University of Pavia reported (Org. Lett. 2013, 15, 2554) the direct carbonylation of 17 to the amide 18. David W. C. MacMillan of Princeton University devised (Science 2013, 339, 1593) a protocol for the β- arylation of an aldehyde 19 to give 20. Directed palladation of distal C–H bonds continues to be developed. Srinivasarao Arulananda Babu of the Indian Institute of Science Education and Research effected (Org. Lett. 2013, 15, 3238) diastereoselective arylation of the cyclopropane 21 with 22 to give 23.
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Taber, Douglass. "Substituted Benzenes: The Alvarez-Manzaneda Synthesis of (-)-Taiwaniquinone G." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0065.

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Continuing efforts toward the direct functionalization of aromatic C-H bonds, Nobutaka Fujii and Hiroaki Ohno of Kyoto University described (Chem. Commun. 2009, 3413) a Pd-mediated protocol for the ortho hydroxylation of aryl tetrahydropyrimidines such as 1. To use a boronic acid as an activating/directing group, Michinori Suginome, also of Kyoto University, devised (J. Am. Chem. Soc. 2009, 131, 7502) the pyrazolylpyridyl derivative 3. The product 4 could be returned to the boronic acid or carried on to the borate ester, in each case with recovery of the directing group. Eiichi Nakamura of the University of Tokyo established (Angew. Chem. Int. Ed. 2009, 49, 2925) that ortho arylation of 5 could be accomplished even in the presence of a reactive aryl halide. In a complementary approach, Matthew J. Gaunt of the University of Cambridge developed (Science 2009, 323, 1593) a procedure for C-H arylation of anilides such as 7 that showed good meta selectivity. Mamoru Tobisu and Naoto Chatani of Osaka University have found (Chem. Lett. 2009, 38, 710) for the conversion of aryl ethers such as 9 to the tertiary amine. Masahito Ochiai of the University of Tokushima observed (J. Am. Chem. Soc. 2009, 131, 8392) the remarkable inversion of an arene sulfonamide such as 11 to the protected aniline 12. Matthias Beller of the Universität Rostock established (Angew. Chem. Int. Ed. 2009, 49, 918) a Pd-mediated procedure for the conversion of even a congested aryl halide 13 to the phenol 14. The first C-C bond formations with phenols used very reactive, but expensive, leaving groups such as triflates. With improving ligand design, conditions have been found that work well even with inexpensive mesylates. Now, Zhang-Jie Shi of Peking University (J. Am. Chem. Soc. 2008, 130, 14468) and Neil K. Garg of UCLA (J. Am. Chem. Soc. 2008, 130, 14422), working independently, developed similar procedures for the Ni-mediated arylation of esters such as 15. Both groups found that pivalates worked particularly well. For some highly-substituted benzene derivatives, construction of the aromatic ring can be an economical approach.
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Taber, Douglass F. "C–H Functionalization: The Snyder Synthesis of (+)-Scholarisine A." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0020.

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Thomas R. Hoye of the University of Minnesota devised (Nature 2013, 501, 531) the reagent 2, that cyclized to a benzyne that in turn dehydrogenated the alkane 1 to the alkene 3, and 4. Abigail G. Doyle of Princeton University developed (J. Am. Chem. Soc. 2013, 135, 12990) a reagent combination for the allylic fluorination of a terminal alkene 5 to the branched product 6. Yan Zhang and Jianbo Wang of Peking University oxidized (Angew. Chem. Int. Ed. 2013, 52, 10573) the methyl group of 7 to give the nitrile 8. Hanmin Huang of the Lanzhou Institute of Chemical Physics found (Org. Lett. 2013, 15, 3370) conditions for the carbonylation of the benzylic site of 9, leading to coupling with 10 to form the amide 11. Yu Rao of Tsinghua University effected (Angew. Chem. Int. Ed. 2013, 52, 13606) the direct methoxylation of 12, to give 13. Pd-mediated methoxylation had previously been described (Chem. Sci. 2013, 4, 4187) by Bing-Feng Shi of Zhejiang University. M. Christina White of the University of Illinois, Urbana found (J. Am. Chem. Soc. 2013, 135, 14052) that with variant ligands on the Fe catalyst, the oxidation of 14 could be directed selectively to either 15 or 16. C–H bonds can also be converted to C–N bonds. Sukbok Chang of KAIST oxi­dized (J. Am. Chem. Soc. 2013, 135, 12861) the unsaturated ester 17 with 18 to form the enamide 18. Gong Chen of Pennsylvania State University cyclized (Angew. Chem. Int. Ed. 2013, 52, 11124) the amide 20 to the γ-lactam 21. Professor Shi reported (Angew. Chem. Int. Ed. 2013, 52, 13588) a related approach to β-lactams. Ethers are easily oxidized. Taking advantage of this, Yun Liang of Hunan Normal University coupled (Synthesis 2013, 45, 3137) the bromoalkyne 23 with tetrahydro­furan 22 to give 24. Guangbin Dong of the University of Texas, Austin devised (J. Am. Chem. Soc. 2013, 135, 17747) a protocol for the β-arylation of ketones, includ­ing the preparation of 27 by the coupling of 25 with 26.
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Liu, Bin, Ye-Qiang Han, Fang Hu, and Bing-Feng Shi. "Palladium-Catalyzed Directed Arylation of Unactivated C(sp 3 ) H Bonds." In Strategies for Palladium-Catalyzed Non-Directed and Directed C-H Bond Functionalization. Elsevier, 2017. http://dx.doi.org/10.1016/b978-0-12-805254-9.00004-9.

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Conference papers on the topic "C-H Direct Arylation"

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Čerňa, Igor, and Michal Hocek. "Direct C–H arylation of purines and purine nucleosides." In XIVth Symposium on Chemistry of Nucleic Acid Components. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2008. http://dx.doi.org/10.1135/css200810327.

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Čerňová, Miroslava, and Michal Hocek. "Dichotomy in regioselectivity of Pd-catalyzed direct C–H arylation of protected uracils." In XVth Symposium on Chemistry of Nucleic Acid Components. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2011. http://dx.doi.org/10.1135/css201112314.

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