Thematische Bibliographien / Au alkynes hydroarylation

Auswahl der wissenschaftlichen Literatur zum Thema „Au alkynes hydroarylation“

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Veröffentlicht am 25. Mai 2024

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Zeitschriftenartikel zum Thema "Au alkynes hydroarylation"

1

Duan, Chang-Lin, Xing-Yu Liu, Yun-Xuan Tan, Rui Ding, Shiping Yang, Ping Tian und Guo-Qiang Lin. „Acetic Acid-Promoted Rhodium(III)-Catalyzed Hydroarylation of Terminal Alkynes“. Synlett 30, Nr. 08 (26.03.2019): 932–38. http://dx.doi.org/10.1055/s-0037-1611780.

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Rhodium(III)-catalyzed hydroarylation of terminal alkynes has not previously been achieved because of the inevitable oligomerization and other side reactions. Here, we report a novel Cp*Rh(III)-catalyzed hydroarylation of terminal alkynes in acetic acid as solvent to facilitate the C–H bond activation and subsequent transformations. This reaction proceeds under mild conditions, providing an effective approach to the synthesis of alkenylated heterocycles in high to excellent yields (31–99%) with a broad substrate scope (37 examples) and good functional-group compatibility. In this transformation, the loading of the alkyne can be reduced to 1.2 equivalents, which indicates the significant role of HOAc in lowering the reaction temperature and suppressing the oligomerization of the terminal alkyne. Preliminary mechanistic studies are also presented.
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2

Tubaro, Cristina, Marco Baron, Andrea Biffis und Marino Basato. „Alkyne hydroarylation with Au N-heterocyclic carbene catalysts“. Beilstein Journal of Organic Chemistry 9 (05.02.2013): 246–53. http://dx.doi.org/10.3762/bjoc.9.29.

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Mono- and dinuclear gold complexes with N-heterocyclic carbene (NHC) ligands have been employed as catalysts in the intermolecular hydroarylation of alkynes with simple unfunctionalised arenes. Both mono- and dinuclear gold(III) complexes were able to catalyze the reaction; however, the best results were obtained with the mononuclear gold(I) complex IPrAuCl. This complex, activated with one equivalent of silver tetrafluoroborate, exhibited under acidic conditions at room temperature much higher catalytic activity and selectivity compared to more commonly employed palladium(II) catalysts. Moreover, the complex was active, albeit to a minor extent, even under neutral conditions, and exhibited lower activity but higher selectivity compared to the previously published complex AuCl(PPh3). Preliminary results on intramolecular hydroarylations using this catalytic system indicate, however, that alkyne hydration by traces of water may become a serious competing reaction.
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Zhang, Chaofeng, Songkui Lv, Yanru Wang, Jingyi Zhang, Xiao-Na Wang und Junbiao Chang. „Metal-free intramolecular hydroarylation of alkynes“. Organic Chemistry Frontiers 9, Nr. 5 (2022): 1300–1307. http://dx.doi.org/10.1039/d1qo01831k.

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An efficient metal-free intramolecular hydroarylation reaction of alkynes is described here. A series of aryl and N-group attached alkynes generated the intramolecular hydroarylation products in high yields.
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Zhao, JiaKai, Qi Mou, RuiHan Niu, RuYuan Zhao und Bo Sun. „Environmentally Friendly Cp*Co(III)-catalyzed C-H Bond Hydroarylation of Alkynes“. Journal of Physics: Conference Series 2076, Nr. 1 (01.11.2021): 012038. http://dx.doi.org/10.1088/1742-6596/2076/1/012038.

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Abstract A facile synthetic method of Alkenylarene derivatives via cobalt(III)-catalyzed C-H hydroarylation with terminal alkynes has been presented. This helpful protocol provides a way to use terminal alkynes to couple with aryl groups through 1, 2-insertion, with high yield and good selectivity to obtain the corresponding hydroarylation products.
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de Mendoza, Paula, und Antonio M. Echavarren. „Synthesis of arenes and heteroarenes by hydroarylation reactions catalyzed by electrophilic metal complexes“. Pure and Applied Chemistry 82, Nr. 4 (10.03.2010): 801–20. http://dx.doi.org/10.1351/pac-con-09-10-06.

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The hydroarylation of alkynes (also known as arylation of alkynes or alkenylation of arenes) catalyzed by gold or other electrophilic metal salts or complexes is reviewed from synthetic and mechanistic perspectives.
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Thowfik, Salam, C. M. A. Afsina und Gopinathan Anilkumar. „Ruthenium-catalyzed hydroarylation reactions as the strategy towards the synthesis of alkylated arenes and substituted alkenes“. RSC Advances 13, Nr. 9 (2023): 6246–63. http://dx.doi.org/10.1039/d3ra00211j.

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Metal catalyzed hydroarylation reactions achieve C–C or C-heteroatom bonds in an atom economical and step economical manner. Here we cover the literature from 2016 to 2022 to summarize the recent advancements in Ru-catalyzed hydroarylation reactions of alkenes and alkynes.
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Panda, Niranjan, Irshad Mattan, Subhadra Ojha und Chandra Shekhar Purohit. „Synthesis of medium-sized (6–7–6) ring compounds by iron-catalyzed dehydrogenative C–H activation/annulation“. Organic & Biomolecular Chemistry 16, Nr. 42 (2018): 7861–70. http://dx.doi.org/10.1039/c8ob01496e.

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Luo, Cuicui, Hongwei Yang, Rongfang Mao, Chunxu Lu und Guangbin Cheng. „An efficient Au(i) catalyst for double hydroarylation of alkynes with heteroarenes“. New Journal of Chemistry 39, Nr. 5 (2015): 3417–23. http://dx.doi.org/10.1039/c4nj02170c.

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9

Yamamoto, Y., E. Ohkubo und M. Shibuya. „Selective synthesis of trisubstituted (trifluoromethyl)alkenes via ligand-free Cu-catalyzed syn hydroarylation, hydroalkenylation and hydroallylation of (trifluoromethyl)alkynes“. Green Chemistry 18, Nr. 17 (2016): 4628–32. http://dx.doi.org/10.1039/c6gc01782g.

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Chen, Bin, Yan Jiang, Jiang Cheng und Jin-Tao Yu. „Rhodium-catalyzed hydroarylation of alkynes via tetrazole-directed C–H activation“. Organic & Biomolecular Chemistry 13, Nr. 10 (2015): 2901–4. http://dx.doi.org/10.1039/c5ob00064e.

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Dissertationen zum Thema "Au alkynes hydroarylation"

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Kanyiva, Kyalo Stephen. „Studies on Nickel-catalyzed Hydroarylation and Hydrocarbamoylation of Alkynes“. 京都大学 (Kyoto University), 2010. http://hdl.handle.net/2433/120819.

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2

Despalle, Alexis. „Développement de nouveaux outils et de nouvelles approches synthétiques pour le contrôle des chiralités centrale, axiale et hélicoïdale“. Electronic Thesis or Diss., Aix-Marseille, 2022. http://www.theses.fr/2022AIXM0130.

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Depuis les travaux pionniers d’Akiyama et Terada en 2004 sur l’utilisation d’organocatalyseurs acides phosphoriques chiraux, de nombreux efforts ont été déployés pour le développement de catalyseurs C2-symétriques à chiralité axiale avec, toutefois, un accès synthétique fastidieux. La synthèse de catalyseurs acides thiophosphi(o)niques originaux P-stéréogènes facilement accessibles et configurationnellement stables a été réalisée et leur réactivité a ensuite été évaluée dans une réaction de Pictet-Spengler énantiosélective avec des résultats préliminaires encourageants. Dans un second projet, nous avons d’abord tenté de développer une nouvelle réaction d’arylation organocatalysée énantiosélective afin d’obtenir des nouveaux atropisomères coumarine-aryle avec des résultats préliminaires prometteurs. Nous avons aussi souhaité développer une méthode de synthèse stéréosélective de furanes possédant deux axes stéréogènes par conversion de chiralité. Ainsi, nous avons d’abord réalisé la synthèse énantiosélective de dihydrofuranes par hétéroannulation avec deux types de nucléophiles et modes d'activation différents. La synthèse de (hétéro) [4]hélicènes configurationnellement stables constitue un défi synthétique car ces molécules racémisent rapidement à température ambiante. Deux hétéro [4]pseudo-hélicènes stables configurationnellement ont été obtenus par hydroarylation intramoléculaire d’alcynes catalysée à l’or. Nous avons également tenté la synthèse de composés [4]hélicéniques par double réaction de Friedel-Crafts organocatalysée par un acide de Brønsted mais les produits souhaités n’ont jamais pu être isolés
Since the pioneering work of Akiyama and Terada in 2004 on the use of chiral phosphoric acid as organocatalysts, a huge amount of efforts has been devoted to the development of C2-axially chiral catalysts. Despite being successful in many transformations, the potential industrial development of this family of catalysts is hampered by a tedious multisteps synthetic access. In this context, the synthesis of easily accessible, configurationally stable P-stereogenic and original thiophosphi(o)nic acid catalysts was achieved and, as a preliminary experiment, they were engaged in an enantioselctive Pictet-Spengler reaction showing very encouraging results. In a second project, we tried to develop a new organocatalyzed enantioselective arylation reaction to obtain new coumarin-aryl atropisomers with promising results. Then, we aimed at developing a new method for the stereoselective synthesis of furans displaying two atropisomericaxis by chirality conversion strategy. We first performed the enantioselective synthesis of dihydrofurans by a heteroannulation. Very promising results were obtained with two types of arylacetyl nucleophiles activated by a bifonctionnal organocatalyst or by a catalytic complex of Ni(II) and chiral diamine.The synthesis of configurationnally stable (hetero) [4]helicenes constitutes a synthetic challenge since these molecules rapidly racemizeat room temperature. Two configurationnally stable hetero [4]pseudo-helicenes were obtained by Au-promoted alkynes intramolecular hydroarylation. We also tried to synthesize [4]helicenic compounds by Brønsted acid organocatalized double Friedel-Crafts reaction. However, the desired products could not be isolated
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Wei, Li-Mei, und 魏麗梅. „Palladium-catalyzed Cross Coupling, Hydroarylation and Ring-expansion Reactions of Aryl Iodides with Alkynes“. Thesis, 2003. http://ndltd.ncl.edu.tw/handle/3ukgx3.

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博士
高雄醫學大學
藥學研究所
91
The chemistry of palladium has been developed in recent years as a powerful method to promote the formation of carbon-carbon bond. In this thesis, we describe the palladium-catalyzed cross-coupling, hydroarylation and ring expansion-addition reactions of aryl iodides with alkynes. Firstly, the reaction of aryl iodides with 2-alkynylbenzonitriles in the presence of Pd(PPh3)4 and NaOCH3 in methanol provided 3-diarylmethylideneisoindoles and 3,4-disubstituted isoquinolines via the cross-coupling and cyclization reaction. Reaction of 2-ethynylbenzonitrile with 2.5 equiv. of iodobenzene gave 3-diphenylmethylideneisoindole in 45% yield along with the minor monocoupled adduct 3-phenylmethylideneisoindole in 6% yield. Secondly, treatment of aryl iodides with disubstituted alkynes in the presence of Pd(OAc)2 and sodium methoxide in methanol afforded trisubstituted ethylenes. The hydrogenolysis of the organopalladium is proposed through β-hydride elimination of the palladium methanolate intermediate. Finally, the one-step synthesis of 2-diarylmethylidenecyclopentanone derivatives was achieved by the palladium-catalyzed tandem rearrangement and addition of 1-ethynylcyclobutanols with aryl iodides. When the catalyst (Pd(OAc))2 was replaced by Pd(dba)2, Pd(OCOCF3)2 or Pd(CH3CN)2Cl2 under the same reaction conditions, 2-diarylmethylidenecyclopentanones were obtained in modest yields. Triethyl amine (Et3N) was the best base, and other bases, such as K2CO3、Na2CO3 and NaOAc, were less effective.
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Buchteile zum Thema "Au alkynes hydroarylation"

1

de Mendoza, Paula, und Antonio M. Echavarren. „Intramolecular Hydroarylation of Alkynes“. In Modern Gold Catalyzed Synthesis, 135–52. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2012. http://dx.doi.org/10.1002/9783527646869.ch5.

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2

Kitamura, Tsugio. „Intramolecular Hydroarylation of Alkynes, Alkenes, and Allenes“. In Transition-Metal-Mediated Aromatic Ring Construction, 455–84. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2013. http://dx.doi.org/10.1002/9781118629871.ch18.

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3

Kirillova, Mariia S., Fedor M. Miloserdov und Antonio M. Echavarren. „Hydroarylation of Alkynes using Cu, Ag, and Au Catalysts“. In Catalytic Hydroarylation of Carbon-Carbon Multiple Bonds, 217–303. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527697649.ch7.

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4

Yoshikai, Naohiko. „Hydroarylation of Alkynes and Alkenes using Group 7-9 First-Row Transition Metal Catalysts“. In Catalytic Hydroarylation of Carbon-Carbon Multiple Bonds, 193–216. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527697649.ch6.

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5

Yamamoto, Yoshihiko. „Catalytic Alkyne Hydroarylation Using Arylboron Reagents, Aryl Halides, and Congeners“. In Catalytic Hydroarylation of Carbon-Carbon Multiple Bonds, 305–59. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2017. http://dx.doi.org/10.1002/9783527697649.ch8.

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6

Malleron, J. L., J. C. Fiaud und J. Y. Legros. „Hydroarylation and Hydrovinylation of Alkenes and Alkynes“. In Handbook of Palladium-Catalyzed Organic Reactions, 102–5. Elsevier, 1997. http://dx.doi.org/10.1016/b978-012466615-3/50017-3.

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7

Periasamy, M., M. Seenivasaperumal und S. Sivakumar. „Rhodium-Catalyzed Hydroarylation of Alkenes and Alkynes by Triarylboroxins“. In Boron Compounds, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-006-00270.

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