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Auteur : Grafiati
Publié le 18 mai 2024

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1

Zhao, Yating, et Wujiong Xia. « Photochemical C–H bond coupling for (hetero)aryl C(sp2)–C(sp3) bond construction ». Organic & ; Biomolecular Chemistry 17, no 20 (2019) : 4951–63. http://dx.doi.org/10.1039/c9ob00244h.

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This review highlights the recent advances in photochemical (hetero)aryl C(sp2)–C(sp3) bond construction via C–H bond coupling such as (hetero)arylation of C(sp3)–H bonds and alkylation of (hetero)aryl C(sp2)–H bonds.
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2

Wei, Kai-Jie, Zheng-jun Quan, Zhang Zhang, Yu-xia Da et Xi-cun Wang. « Direct C–H heteroarylation of azoles with 1,2-di(pyrimidin-2-yl)disulfides through C–S cleavage of disulfides ». RSC Advances 6, no 81 (2016) : 78059–63. http://dx.doi.org/10.1039/c6ra18997k.

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3

Roth-Barton, Jesse, Yit Wooi Goh, Asimo Karnezis et Jonathan M. White. « Structural Studies on α-Pyrone Cycloadducts. Manifestation of the Early Stages of CO2 Extrusion by retro Hetero-Diels - Alder Reaction ». Australian Journal of Chemistry 62, no 5 (2009) : 407. http://dx.doi.org/10.1071/ch09018.

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Structures of the α-pyrone (pyran-2-one) cycloadducts 4–8 show deviations of some bond distances from their normal values, consistent with manifestation of the early stages of the retro hetero-Diels–Alder decarboxylation reaction in the ground state structures. Thus the bridgehead C–O(CO) and C–CO(O) bonds are lengthened and the bridging C–O bond is shortened. The degree of lengthening of the C–O(CO) and C–CO(O) bonds is similar, whereas in the calculated transition state structure there is significant asymmetry in the extent of C–CO(O) and C–O(CO) bond breaking.
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4

Correa, Arkaitz, et Marcos Segundo. « Cross-Dehydrogenative Coupling Reactions for the Functionalization of α-Amino Acid Derivatives and Peptides ». Synthesis 50, no 15 (25 juin 2018) : 2853–66. http://dx.doi.org/10.1055/s-0037-1610073.

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The functionalization of typically unreactive C(sp3)–H bonds holds great promise for reducing the reliance on existing functional groups while improving atom-economy and energy efficiency. As a result, this topic is a matter of genuine concern for scientists in order to achieve greener chemical processes. The site-specific modification of α-amino acid and peptides based upon C(sp3)–H functionalization still represents a great challenge of utmost synthetic importance. This short review summarizes the most recent advances in ‘Cross-Dehydrogenative Couplings’ of α-amino carbonyl compounds and peptide derivatives with a variety of nucleophilic coupling partners.1 Introduction2 C–C Bond-Forming Oxidative Couplings2.1 Reaction with Alkynes2.2 Reaction with Alkenes2.3 Reaction with (Hetero)arenes2.4 Reaction with Alkyl Reagents3 C–Heteroatom Bond-Forming Oxidative Couplings3.1 C–P Bond Formation3.2 C–N Bond Formation3.3 C–O and C–S Bond Formation4 Conclusions
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5

Yang, Tao, Congshan Zhou, Zan Yang, Jiao Li, Jie Hua et Jianmin Yi. « KI/K2S2O8-Mediated α-C–H Sulfenylation of Carbonyl Compounds with (Hetero)Aryl Thiols ». Synlett 28, no 17 (13 juillet 2017) : 2325–29. http://dx.doi.org/10.1055/s-0036-1588483.

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A new and facile KI/K2S2O8-mediated α-C–H sulfenylation of carbonyl compounds with (hetero)aryl thiols was developed for the formation of C–S bond at room temperature. This method provided a simple process for the synthesis of β-keto thioethers in moderate to excellent yields. A variety of carbonyl compounds and (hetero)aryl thiols were tolerated in this reaction.
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6

Zhang, Zuxiao, Leah M. Stateman et David A. Nagib. « δ C–H (hetero)arylationviaCu-catalyzed radical relay ». Chemical Science 10, no 4 (2019) : 1207–11. http://dx.doi.org/10.1039/c8sc04366c.

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A radical relay strategy has been developed to enable selective δ C–H arylation. The approach employs a chiral copper catalyst, which serves the dual roles of generating an N-centered radical to promote intramolecular H-atom transfer, and then intercepting a distal C-centered radical for C–C bond formation with (hetero)aryl boronic acids.
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7

Knochel, Paul, Maximilian Hofmayer, Jeffrey Hammann et Gérard Cahiez. « Iron-Catalyzed C(sp2)–C(sp3) Cross-Coupling Reactions of Di(hetero)arylmanganese Reagents and Primary and Secondary Alkyl Halides ». Synlett 29, no 01 (30 août 2017) : 65–70. http://dx.doi.org/10.1055/s-0036-1590891.

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An iron-catalyzed cross-coupling between di(hetero)arylmanganese reagents and primary and secondary alkyl halides is reported. No rearrangement of secondary alkyl halides to unbranched products was observed in these C–C bond-forming reactions.
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8

Irgashev, Roman A., Arseny A. Karmatsky, Gennady L. Rusinov et Valery N. Charushin. « A new and convenient synthetic way to 2-substituted thieno[2,3-b]indoles ». Beilstein Journal of Organic Chemistry 11 (11 juin 2015) : 1000–1007. http://dx.doi.org/10.3762/bjoc.11.112.

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A short and robust approach for the synthesis of 2-(hetero)aryl substituted thieno[2,3-b]indoles from easily available 1-alkylisatins and acetylated (hetero)arenes has been advanced. The two-step procedure includes the “aldol-crotonic” type of condensation of the starting materials, followed by treatment of the intermediate 3-(2-oxo-2-(hetero)arylethylidene)indolin-2-ones with Lawesson’s reagent. The latter process involves two sequential reactions, namely reduction of the C=C ethylidene double bond of the intermediate indolin-2-ones followed by the Paal–Knorr cyclization, thus affording tricyclic thieno[2,3-b]indoles.
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9

Ge, Danhua, et Xue-Qiang Chu. « Multiple-fold C–F bond functionalization for the synthesis of (hetero)cyclic compounds : fluorine as a detachable chemical handle ». Organic Chemistry Frontiers 9, no 7 (2022) : 2013–55. http://dx.doi.org/10.1039/d1qo01749g.

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10

Chupakhin, O. N., A. V. Shchepochkin et V. N. Charushin. « Atom- and step-economical nucleophilic arylation of azaaromatics via electrochemical oxidative cross C–C coupling reactions ». Green Chemistry 19, no 13 (2017) : 2931–35. http://dx.doi.org/10.1039/c7gc00789b.

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A simple and efficient electrochemical method for the synthesis of asymmetrical bi(het)aryls through direct functionalization of the C(sp2)–H bond in azaaromatics with fragments of (hetero)aromatic nucleophiles has been developed.
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11

Albano, Gianluigi, Angela Punzi, Maria Annunziata M. Capozzi et Gianluca M. Farinola. « Sustainable protocols for direct C–H bond arylation of (hetero)arenes ». Green Chemistry 24, no 5 (2022) : 1809–94. http://dx.doi.org/10.1039/d1gc03168f.

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A comprehensive and critical overview of the sustainable strategies for direct C–H bond arylation of (hetero)arenes, based on the use of recoverable catalysts, sustainable solvents and non-conventional energy sources, has been performed.
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12

Hagui, Wided, Néji Besbes, Ezzeddine Srasra, Jean-François Soulé et Henri Doucet. « Direct access to 2-(hetero)arylated pyridines from 6-substituted 2-bromopyridines via phosphine-free palladium-catalyzed C–H bond arylations : the importance of the C6 substituent ». RSC Advances 6, no 21 (2016) : 17110–17. http://dx.doi.org/10.1039/c6ra01861k.

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13

Tabasso, Silvia, Emanuela Calcio Gaudino, Elisa Acciardo, Maela Manzoli, Agnese Giacomino et Giancarlo Cravotto. « Microwave-Assisted Dehydrogenative Cross Coupling Reactions in γ-valerolactone with a Reusable Pd/β-cyclodextrin Crosslinked Catalyst ». Molecules 24, no 2 (14 janvier 2019) : 288. http://dx.doi.org/10.3390/molecules24020288.

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Transition-metal mediated C–H bond activation and functionalization is one of the most straightforward and powerful tools in modern organic synthetic chemistry. Oxidative C–H/C–H coupling reactions between two (hetero)arenes under heterogeneous catalysis may be a valuable means for the production of a plethora of bi(hetero)aryls, and one that adheres to the increasing demand for atom-economic and sustainable chemistry. We have therefore developed a reusable heterogeneous catalytic system, which is based on Pd cross-linked β-cyclodextrin, to perform an efficient microwave-assisted oxidative C–H/C–H cross coupling process between benzothiazoles and methyl thiophene in the presence of green solvents.
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14

Sharma, Ruchi, et M. Ramu Yadav. « Recent developments in decarboxylative C(aryl)–X bond formation from (hetero)aryl carboxylic acids ». Organic & ; Biomolecular Chemistry 19, no 25 (2021) : 5476–500. http://dx.doi.org/10.1039/d1ob00675d.

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This review highlights the recent developments in ipso-decarboxylative C–X (X = O/N/halo/S/Se/P/CN) bond formation using (hetero)aryl carboxylic acids, which are economical and environmentally benign starting materials.
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15

Zhou, Ming-Bo, Rui Pi, Fan Teng, Yang Li et Jin-Heng Li. « Ring-opening formal hetero-[5+2] cycloaddition of 1-tosyl-2,3-dihydro-1H-pyrroles with terminal alkynes : entry to 1-tosyl-2,3-dihydro 2,3-dihydro-1H-azepines ». Chemical Communications 55, no 75 (2019) : 11295–98. http://dx.doi.org/10.1039/c9cc05082e.

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16

Li, Mengli, Xing Li, Honghong Chang, Wenchao Gao et Wenlong Wei. « Palladium-catalyzed direct C–H arylation of pyridine N-oxides with potassium aryl- and heteroaryltrifluoroborates ». Organic & ; Biomolecular Chemistry 14, no 8 (2016) : 2421–26. http://dx.doi.org/10.1039/c5ob02409a.

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An efficient ligand-free Pd(OAc)2-catalyzed selective arylation of pyridine N-oxides using potassium (hetero)aryltrifluoroborates as coupling partners via C–H bond activation was achieved in the presence of TBAI.
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17

Cui, Bingcun, Guosheng Huang, Jin Liu, Shaofen Jin, Yingxing Zhou, Dongmei Ni, Tingting Liu, Gang Hu et Xin Yu. « Palladium-Catalyzed ortho-Monoacylation of Arenes with Aldehydes­ via 1,2,4-Benzotriazine-Directed C–H Bond Activation ». Synthesis 52, no 09 (10 février 2020) : 1407–16. http://dx.doi.org/10.1055/s-0039-1691564.

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An efficient palladium-catalyzed C–H bond functionalization/ortho-monoacylation reaction of 3-aryl-1,2,4-benzotriazines with (hetero)aryl or alkyl aldehydes has been developed, which offers a facile and alternative strategy for direct modification and further diversification of 3-aryl-1,2,4-benzotriazines. Bioactive 1,2,4-benzotriazine has been employed as a novel directing group for the palladium-catalyzed regioselective monoacylation of sp2 C–H bond protocol with broad substrate scope and good functional group tolerance.
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18

Welsh, Thomas A., Audrey Laventure, Thomas Baumgartner et Gregory C. Welch. « Dithienophosphole-based molecular electron acceptors constructed using direct (hetero)arylation cross-coupling methods ». Journal of Materials Chemistry C 6, no 8 (2018) : 2148–54. http://dx.doi.org/10.1039/c7tc05631a.

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Herein we report on the first successful coupling of the dithienophosphole (S2PO) functional building block with three types of heteroaryl end caps using direct (hetero)arylation C–H bond functionalization methods.
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19

Punji, Benudhar, et Muniyappa Vijaykumar. « Advances in Transition-Metal-Catalyzed C–H Bond Oxygenation of Amides ». Synthesis 53, no 17 (13 avril 2021) : 2935–46. http://dx.doi.org/10.1055/a-1481-2584.

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AbstractC–O bond formation represents a fundamental chemical transformation in organic synthesis to develop valuably oxygenated (hetero)arenes. Particularly, the direct and regioselective C–H bond oxygenation of privileged amides, using a transition metal catalyst and a mild oxygenating source, is a step-economy and attractive approach. During the last decade, considerable progress has been realized in the direct C–H oxygenation of primary, secondary, and tertiary amides. This Short Review compiles the advances in transition-metal-catalyzed oxygenation of C(sp2)–H and C(sp3)–H bonds on various amides with diverse oxygenation sources. The review is categorized into two different major sections: (i) C(sp2)–H oxygenation and (ii) C(sp3)–H oxygenation. Each section is discussed based on the directing group (monodentate and bidentate) attached to the amide derivatives.1 Introduction2 C(sp2)–H Oxygenation2.1 Monodentate Directed2.2 Bidentate Directed3 C(sp3)–H Oxygenation3.1 Monodentate Directed3.2 Bidentate Directed4 Conclusion and Outlook
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20

Yamada, Tsuyoshi, Jing Jiang, Naoya Ito, Kwihwan Park, Hayato Masuda, Chikara Furugen, Moeka Ishida, Seiya Ōtori et Hironao Sajiki. « Development of Facile and Simple Processes for the Heterogeneous Pd-Catalyzed Ligand-Free Continuous-Flow Suzuki–Miyaura Coupling ». Catalysts 10, no 10 (19 octobre 2020) : 1209. http://dx.doi.org/10.3390/catal10101209.

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The Suzuki–Miyaura coupling reaction is one of the most widely utilized C–C bond forming methods to create (hetero)biaryl scaffolds. The continuous-flow reaction using heterogeneous catalyst-packed cartridges is a practical and efficient synthetic method to replace batch-type reactions. A continuous-flow ligand-free Suzuki–Miyaura coupling reaction of (hetero)aryl iodides, bromides, and chlorides with (hetero)aryl boronic acids was developed using cartridges packed with spherical resin (tertiary amine-based chelate resin: WA30)-supported palladium catalysts (7% Pd/WA30). The void space in the cartridge caused by the spherical catalyst structures enables the smooth flow of a homogeneously dissolved reaction solution that consists of a mixture of organic and aqueous solvents and is delivered by the use of a single syringe pump. Clogging or serious backpressure was not observed.
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21

Frogley, Benjamin J., et Anthony F. Hill. « Metal coordination to bipyridyl carbynes ». Dalton Transactions 49, no 10 (2020) : 3272–83. http://dx.doi.org/10.1039/c9dt04744a.

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A new synthetic approach to hetero-aryl substituted carbyne complexes has allowed the synthesis of bipyridyl functionalised carbynes and bis(carbynes) with three potential sites for metal coordination to either the two pyridyl donors or the WC bond.
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22

Varala, Ravi, Vittal Seema et Narsimhaswamy Dubasi. « Phenyliodine(III)diacetate (PIDA) : Applications in Organic Synthesis ». Organics 4, no 1 (23 décembre 2022) : 1–40. http://dx.doi.org/10.3390/org4010001.

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One of the hypervalent iodines most widely used as an oxidizing agent in organic chemistry is (diacetoxyiodo)benzene (PhI(OAc)2), also known as (DAIB), phenyliodine(III) diacetate (PIDA). In this septennial mini-review, the authors have concisely and systematically presented representative applications of PIDA in organic synthesis involving C-H functionalization, hetero-hetero bond formations, heterocyclic ring construction, rearrangements or migrations and miscellaneous reactions along with their interesting mechanistic aspects starting from the summer of 2015 to the present.
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23

Pacheco-Benichou, Alexandra, Eugénie Ivendengani, Ioannis K. Kostakis, Thierry Besson et Corinne Fruit. « Copper-Catalyzed C–H Arylation of Fused-Pyrimidinone Derivatives Using Diaryliodonium Salts ». Catalysts 11, no 1 (29 décembre 2020) : 28. http://dx.doi.org/10.3390/catal11010028.

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Copper-catalyzed Csp2–Csp2 bond forming reactions through C–H activation are still one of the most useful strategies for the diversification of heterocyclic moieties using various coupling partners. A catalytic protocol for the C–H (hetero)arylation of thiazolo[5,4-f]quinazolin-9(8H)-ones and more generally fused-pyrimidinones using catalyst loading of CuI with diaryliodonium triflates as aryl source under microwave irradiation has been disclosed. The selectivity of the transfer of the aryl group was also disclosed in the case of unsymmetrical diaryliodonium salts. Specific phenylation of valuable fused-pyrimidinones including quinazolinone are provided. This strategy enables a rapid access to an array of various (hetero)arylated N-containing polyheteroaromatics as new potential bioactive compounds.
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24

Le Bras, Jean, et Jacques Muzart. « Pd-Catalyzed Intermolecular Dehydrogenative Heck Reactions of Five-Membered Heteroarenes ». Catalysts 10, no 5 (19 mai 2020) : 571. http://dx.doi.org/10.3390/catal10050571.

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The Pd-mediated cross-coupling of (hetero)arenes with alkenes may be an effective method for the formation of a C–C bond from two C–H bonds. Discovered by Fujiwara and co-workers in 1967, this reaction led to a number of reports that we firstly highlighted in 2011 (review with references till June 2010) and for which, we retained the name “dehydrogenative Heck reaction”. The topic, especially the reactions of five-membered heteroarenes, has been the subject of intensive research over the last ten years. The present review is limited to these dehydrogenative Heck reactions published since 2010, underlining the progress of the procedures.
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25

Lipp, Benjamin, Alexander Lipp, Heiner Detert et Till Opatz. « Light-Induced Alkylation of (Hetero)aromatic Nitriles in a Transition-Metal-Free C–C-Bond Metathesis ». Organic Letters 19, no 8 (7 avril 2017) : 2054–57. http://dx.doi.org/10.1021/acs.orglett.7b00652.

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26

Guchhait, Sankar, Maneesh Kashyap et Shuddham Saraf. « Direct C-H Bond Arylation of (Hetero)arenes with Aryl and Heteroarylboronic Acids ». Synthesis 2010, no 07 (20 janvier 2010) : 1166–70. http://dx.doi.org/10.1055/s-0029-1219234.

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27

Brahim, Mariem, Hamed Ben Ammar, Jean-François Soulé et Henri Doucet. « Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group ». Beilstein Journal of Organic Chemistry 12 (17 octobre 2016) : 2197–203. http://dx.doi.org/10.3762/bjoc.12.210.

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The use of a bromo-substituent as blocking group at the C2-position of 3-substituted thiophenes allows the regioselective introduction of aryl substituents at C5-position via Pd-catalysed direct arylation. With 1 mol % of a phosphine-free Pd catalyst, KOAc as the base and DMA as the solvent and various electron-deficient aryl bromides as aryl sources, C5-(hetero)arylated thiophenes were synthesized in moderate to high yields, without cleavage of the thienyl C–Br bond. Moreover, sequential direct thienyl C5-arylation followed by Pd-catalysed direct arylation or Suzuki coupling at the C2-position allows to prepare 2,5-di(hetero)arylated thiophenes bearing two different (hetero)aryl units in only two steps. This method provides a “green” access to arylated thiophene derivatives as it reduces the number of steps to prepare these compounds and also the formation of wastes.
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28

Kang, Qing-Qing, Wenfeng Wu, Qiang Li et Wen-Ting Wei. « Photochemical strategies for C–N bond formation via metal catalyst-free (hetero) aryl C(sp2)–H functionalization ». Green Chemistry 22, no 10 (2020) : 3060–68. http://dx.doi.org/10.1039/d0gc01088j.

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Mahajan, Bhushan, Dnyaneshwar Aand et Ajay K. Singh. « Silver‐Catalyzed Arylation of (Hetero)arenes via Oxidative Benzylic C−C Bond Cleavage of Benzyl Alcohols/ Benzaldehyde ». ChemistrySelect 3, no 43 (23 novembre 2018) : 12336–40. http://dx.doi.org/10.1002/slct.201803215.

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30

Liu, Kai-Hui, Guang-Qi Hu, Cai-Xia Wang, Fei-Fei Sheng, Jing-Wen Bai, Jian-Guo Gu et Hong-Hai Zhang. « C–H Bond Functionalization of (Hetero)aryl Bromide Enabled Synthesis of Brominated Biaryl Compounds ». Organic Letters 23, no 15 (16 juillet 2021) : 5626–30. http://dx.doi.org/10.1021/acs.orglett.1c01613.

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31

Vogel, Pierre, et José Angel Sordo Gonzalo. « Expeditious Asymmetric Synthesis of Polypropionates Relying on Sulfur Dioxide-Induced C–C Bond Forming Reactions ». Catalysts 11, no 11 (21 octobre 2021) : 1267. http://dx.doi.org/10.3390/catal11111267.

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For a long time, the organic chemistry of sulfur dioxide (SO2) consisted of sulfinates that react with carbon electrophiles to generate sulfones. With alkenes and other unsaturated compounds, SO2 generates polymeric materials such as polysulfones. More recently, H-ene, sila-ene and hetero-Diels–Alder reactions of SO2 have been realized under conditions that avoid polymer formation. Sultines resulting from the hetero-Diels–Alder reactions of conjugated dienes and SO2 are formed more rapidly than the corresponding more stable sulfolenes resulting from the cheletropic additions. In the presence of a protic or Lewis acid catalyst, the sultines derived from 1-alkoxydienes are ionized into zwitterionic intermediates bearing 1-alkoxyallylic cation moieties which react with electro-rich alkenes such as enol silyl ethers and allylsilanes with high stereoselectivity. (C–C-bond formation through Umpolung induced by SO2). This produces silyl sulfinates that react with carbon electrophiles to give sulfones (one-pot four component asymmetric synthesis of sulfones), or with Cl2, generating the corresponding sulfonamides that can be reacted in situ with primary and secondary amines (one-pot four component asymmetric synthesis of sulfonamides). Alternatively, Pd-catalyzed desulfinylation generates enantiomerically pure polypropionate stereotriads in one-pot operations. The chirons so obtained are flanked by an ethyl ketone moiety on one side and by a prop-1-en-1-yl carboxylate group on the other. They are ready for two-directional chain elongations, realizing expeditious synthesis of long-chain polypropionates and polyketides. The stereotriads have also been converted into simpler polypropionates such as the cyclohexanone moiety of baconipyrone A and B, Kishi’s stereoheptad unit of rifamycin S, Nicolaou’s C1–C11-fragment and Koert’s C16–CI fragment of apoptolidin A. This has also permitted the first total synthesis of (-)-dolabriferol.
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32

Shokol, Tetyana, Natalia Gorbulenko et Volodymyr Khilya. « Synthesis of chromones, annulated with oxygen-containing heterocycles with two hetero atoms at C(7)-C(8) bond ». French-Ukrainian Journal of Chemistry 7, no 1 (2019) : 121–39. http://dx.doi.org/10.17721/fujcv7i1p121-139.

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The present review represented the advanced synthetic strategies for chromones annulated at the C(7)-C(8) bond with five-membered, six-membered, and seven-membered oxygen-containing heterocycles with two heteroatoms, such as 6H-[1,3]dioxolo[4,5-h]chromen-6-one, 2,3-dihydro-7H-[1,4]dioxino[2,3-h]chromen-7-one, 3,4-dihydro-2H,8H-[1,4]dioxepino[2,3-h]chromen-8-one, 2,3-dihydro-1H,7H-chromeno[7,8-b][1,4]oxazin-7-one, 4H,12H-pyrano[2,3-a]phenoxazine-4-one and 9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one. The biological activity of naturally occurring and modified synthetic fused hetarenochromones has been also highlighted.
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33

Ding, Chengrong, Guofu Zhang, Lidi Xuan et Yiyong Zhao. « Sulfuryl Fluoride Promoted Thiocyanation of Alcohols : A Practical Method for Preparing Thiocyanates ». Synlett 31, no 14 (16 juin 2020) : 1413–17. http://dx.doi.org/10.1055/s-0040-1707151.

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A novel SO2F2-promoted thiocyanation method for the one-step synthesis of thiocyanates through C–O bond cleavage of readily available alcohols with ammonium thiocyanate as the thiocyanating agent was developed. The method avoids the use of additional catalyst, and a variety of (hetero)arene, alkene and aliphatic alcohols reacted with high efficiency in ethyl acetate under mild conditions to afford the corresponding thiocyanates in excellent to quantitative yields with broad functional-group compatibility.
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Mao, Wenbin, et Chen Zhu. « C–C Bond (Hetero)arylation of Ring-Fused Benzocyclobutenols and Application in the Assembly of Polycyclic Aromatic Hydrocarbons ». Journal of Organic Chemistry 82, no 17 (23 août 2017) : 9133–43. http://dx.doi.org/10.1021/acs.joc.7b01727.

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Ma, Changle, Danielle Hagstrom, Soumi Guha Polley et Suresh Subramani. « Redox-regulated Cargo Binding and Release by the Peroxisomal Targeting Signal Receptor, Pex5 ». Journal of Biological Chemistry 288, no 38 (31 juillet 2013) : 27220–31. http://dx.doi.org/10.1074/jbc.m113.492694.

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In its role as a mobile receptor for peroxisomal matrix cargo containing a peroxisomal targeting signal called PTS1, the protein Pex5 shuttles between the cytosol and the peroxisome lumen. Pex5 binds PTS1 proteins in the cytosol via its C-terminal tetratricopeptide domains and delivers them to the peroxisome lumen, where the receptor·cargo complex dissociates. The cargo-free receptor is exported to the cytosol for another round of import. How cargo release and receptor recycling are regulated is poorly understood. We found that Pex5 functions as a dimer/oligomer and that its protein interactions with itself (homo-oligomeric) and with Pex8 (hetero-oligomeric) control the binding and release of cargo proteins. These interactions are controlled by a redox-sensitive amino acid, cysteine 10 of Pex5, which is essential for the formation of disulfide bond-linked Pex5 forms, for high affinity cargo binding, and for receptor recycling. Disulfide bond-linked Pex5 showed the highest affinity for PTS1 cargo. Upon reduction of the disulfide bond by dithiothreitol, Pex5 transitioned to a noncovalent dimer, concomitant with the partial release of PTS1 cargo. Additionally, dissipation of the redox balance between the cytosol and the peroxisome lumen caused an import defect. A hetero-oligomeric interaction between the N-terminal domain (amino acids 1–110) of Pex5 and a conserved motif at the C terminus of Pex8 further facilitates cargo release, but only under reducing conditions. This interaction is also important for the release of PTS1 proteins. We suggest a redox-regulated model for Pex5 function during the peroxisomal matrix protein import cycle.
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Li, Yahui, et Xiao‐Feng Wu. « Direct C−H Bond Borylation of (Hetero)Arenes : Evolution from Noble Metal to Metal Free ». Angewandte Chemie International Edition 59, no 5 (27 janvier 2020) : 1770–74. http://dx.doi.org/10.1002/anie.201914914.

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Guchhait, Sankar K., Maneesh Kashyap et Shuddham Saraf. « ChemInform Abstract : Direct C-H Bond Arylation of (Hetero)arenes with Aryl and Heteroarylboronic Acids ». ChemInform 41, no 31 (9 juillet 2010) : no. http://dx.doi.org/10.1002/chin.201031099.

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Rodrigues, Janh, Sumbal Saba, Antônio C. Joussef, Jamal Rafique et Antonio L. Braga. « KIO3 -Catalyzed C(sp2 )-H Bond Selenylation/Sulfenylation of (Hetero)arenes : Synthesis of Chalcogenated (Hetero)arenes and their Evaluation for Anti-Alzheimer Activity ». Asian Journal of Organic Chemistry 7, no 9 (21 août 2018) : 1819–24. http://dx.doi.org/10.1002/ajoc.201800346.

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Albano, Gianluigi, Gianfranco Decandia, Maria Annunziata M. Capozzi, Nicola Zappimbulso, Angela Punzi et Gianluca M. Farinola. « Infrared Irradiation‐Assisted Solvent‐Free Pd‐Catalyzed (Hetero)aryl‐aryl Coupling via C−H Bond Activation ». ChemSusChem 14, no 16 (22 juillet 2021) : 3391–401. http://dx.doi.org/10.1002/cssc.202101070.

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Ackermann, Lutz. « Metal-catalyzed direct alkylations of (hetero)arenes via C–H bond cleavages with unactivated alkyl halides ». Chemical Communications 46, no 27 (2010) : 4866. http://dx.doi.org/10.1039/c0cc00778a.

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Hagui, Wided, Henri Doucet et Jean-François Soulé. « Application of Palladium-Catalyzed C(sp2)–H Bond Arylation to the Synthesis of Polycyclic (Hetero)Aromatics ». Chem 5, no 8 (août 2019) : 2006–78. http://dx.doi.org/10.1016/j.chempr.2019.06.005.

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Hagui, Wided, Henri Doucet et Jean-François Soulé. « Application of Palladium-Catalyzed C(sp2)–H Bond Arylation to the Synthesis of Polycyclic (Hetero)Aromatics ». Chem 5, no 8 (août 2019) : 2277. http://dx.doi.org/10.1016/j.chempr.2019.07.004.

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Rohokale, Rajendra S., Rupali G. Kalshetti et Chepuri V. Ramana. « Iridium(III)-Catalyzed Alkynylation of 2-(Hetero)arylquinazolin-4-one Scaffolds via C–H Bond Activation ». Journal of Organic Chemistry 84, no 5 (28 janvier 2019) : 2951–61. http://dx.doi.org/10.1021/acs.joc.8b02738.

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Du, Bao-Xin, Zheng-Jun Quan, Yu-Xia Da, Zhang Zhang et Xi-Cun Wang. « ChemInform Abstract : Chemo-Controlled Cross-Coupling of Di(hetero)aryl Disulfides with Grignard Reagents : C-C vs.C-S Bond Formation. » ChemInform 46, no 33 (28 juillet 2015) : no. http://dx.doi.org/10.1002/chin.201533208.

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Satriani, Igor Levi, Rahmawati Munir, Adrianus Inu Natalisanto et Dadan Hamdani. « Analysis of ITO/a-Si:H(p)/a-Si:H(i)/c-Si(n)/Al HIT (Heterostructure with Intrinsic Thin Layer) solar cell performances. » ELKHA 15, no 1 (18 avril 2023) : 11. http://dx.doi.org/10.26418/elkha.v15i1.61351.

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Numerical simulation on HIT (Heterostructure with Intrinsic Thin Layer) solar cell using hetero-structure ITO/(p+)a-Si:H/(i)a-Si:H/(n)c-Si/Al solar cell has been done using AFORS-HET (Automate For Simulation of Heterostructure) software. The purpose of this study is to provide validation as well optimization model of solar cell enhanced performances. Data analysis shows a significant increase on solar power generation. An intrinsic thin layer given between the hetero-interface to reduce defect properties on solar cell structure. The optimization using an optimal value of acceptor-donor doping, dangling-bond defects ( ), thin conductive oxide work function ( ), and other input shows a reducing recombination-rates, as a validation Figure of Merits (FOMs) data reach a maximum efficiency value at 23,67% ( = 634,2 mV; = 51,2 mA/cm2; = 72,91%, this result achieved on peak data such = 5,2 eV, Na (doping) = 5.0 x 1019 cm-3, = 1.0 x 1018 cm-3, (interface defect) = 1.0 x 1010 cm-3. The results obtained from this simulation produce a number of optimum parameters that can be followed up experimentally to obtain better solar cell performances.
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Garcias-Morales, Cesar, David Ortegón-Reyna et Armando Ariza-Castolo. « Investigation of the role of stereoelectronic effects in the conformation of piperidones by NMR spectroscopy and X-ray diffraction ». Beilstein Journal of Organic Chemistry 11 (22 octobre 2015) : 1973–84. http://dx.doi.org/10.3762/bjoc.11.213.

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This paper reports the synthesis of a series of piperidones 1–8 by the Mannich reaction and analysis of their structures and conformations in solution by NMR and mass spectrometry. The six-membered rings in 2,4,6,8-tetraphenyl-3,7-diazabicyclo[3.3.1]nonan-9-ones, compounds 1 and 2, adopt a chair–boat conformation, while those in 2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-ones, compounds 3–8, adopt a chair–chair conformation because of stereoelectronic effects. These stereoelectronic effects were analyzed by the 1 J C–H coupling constants, which were measured in the 13C satellites of the 1H NMR spectra obtained with the hetero-dqf pulse sequence. In the solid state, these stereoelectronic effects were investigated by measurement of X-ray diffraction data, the molecular geometry (torsional bond angles and bond distances), and inter- and intramolecular interactions, and by natural bond orbital analysis, which was performed using density functional theory at the ωB97XD/6311++G(d,p) level. We found that one of the main factors influencing the conformational stability of 3–8 is the interaction between the lone-pair electrons of nitrogen and the antibonding sigma orbital of C(7)–Heq (nN→σ*C–H(7)eq), a type of hyperconjugative interaction.
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Walia, Preet Kamal, Manoj Kumar et Vandana Bhalla. « Tailoring of Hetero-oligophenylene Stabilized Nanohybrid Materials : Potential Tandem Photo-Promoted Systems for C-C and C-X Bond Formation Reactions via C-H Activation ». ChemistrySelect 2, no 13 (2 mai 2017) : 3758–68. http://dx.doi.org/10.1002/slct.201700101.

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Majee, Suman, Devalina Ray et Bimal KrishnaBanik. « Samarium-Mediated Asymmetric Synthesis ». Catalysts 13, no 1 (24 décembre 2022) : 24. http://dx.doi.org/10.3390/catal13010024.

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Samarium is an efficient reducing agent, a radical generator in cyclization and a cascade addition reaction. Interestingly, samarium metal has crucial impact on numerous C-C and C-X (X = hetero atom) bond forming transformations. It has been established as an exceptional chemo-selective and stereoselective reagent. The reactivity of the samarium catalyst/reagent is remarkably enhanced in the presence of various additives, ligands and solvents through effective coordination and an increase in reduction potential. It has inherent character to act as electron donor for a wide range of transformations including the asymmetric version of various reactions. This review accentuates the developments in samarium-mediated/catalyzed asymmetric organic synthesis over the past 12 years, where the chirality has been induced from ligand, a nearby asymmetric center within the substrate or through coordination directed stereospecific reactions.
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Mal, Sourav, Manoranjan Jana et Satinath Sarkar. « Recent Update on Transition Metal‐Free C(sp 2 )−H Bond Halogenation in (Hetero) Arenes ». ChemistrySelect 6, no 41 (2 novembre 2021) : 11299–330. http://dx.doi.org/10.1002/slct.202102956.

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Lu, Ming-Zhu, Ping Lu, Yun-He Xu et Teck-Peng Loh. « Mild Rh(III)-Catalyzed Direct C–H Bond Arylation of (Hetero)Arenes with Arylsilanes in Aqueous Media ». Organic Letters 16, no 10 (30 avril 2014) : 2614–17. http://dx.doi.org/10.1021/ol500754h.

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