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Littérature scientifique sur le sujet « Coupling reactions via aryne intermediates »

Auteur : Grafiati
Publié le 19 avril 2025

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Articles de revues sur le sujet "Coupling reactions via aryne intermediates"

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Kobayashi, Tsuneyuki, Takamitsu Hosoya et Suguru Yoshida. « Facile Synthetic Methods for Diverse N-Arylphenylalanine Derivatives via Transformations of Aryne Intermediates and Cross-Coupling Reactions ». Bulletin of the Chemical Society of Japan 94, no 7 (15 juillet 2021) : 1823–32. http://dx.doi.org/10.1246/bcsj.20210149.

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Surina, Anastasia, Karolína Salvadori, Matěj Poupě, Jan Čejka, Ludmila Šimková et Pavel Lhoták. « Upper Rim-Bridged Calix[4]arenes via Cyclization of meta Alkynyl Intermediates with Diphenyl Diselenide ». Molecules 29, no 6 (11 mars 2024) : 1237. http://dx.doi.org/10.3390/molecules29061237.

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A Sonogashira coupling of meta-iodocalix[4]arene with various terminal acetylenes confirmed that the meta position of calixarene is well addressable, and that both thermal and microwave protocols led to good yields of alkynylcalixarenes. Alkynes thus obtained were subjected to the ferric chloride and diphenyl diselenide-promoted electrophilic closure. It turns out that the calix[4]arenes give completely different bridging products than those described for the non-macrocyclic starting compounds. This can be demonstrated not only by the isolation of products with a six-membered ring (6-exo-dig), but mainly by the smooth formation of the 5-endo-dig cyclization, which has never been observed in the aliphatic series. An attempt at electrocyclization led to a high yield of the 1,2-diketone (oxidation of the starting alkyne), again in contrast to the reaction described for the acyclic derivatives. The structures of the unexpected products were unequivocally established by X-ray analysis and clearly demonstrate how the preorganized macrocyclic skeleton favors a completely different regioselectivity of cyclization reactions compared to common aliphatic compounds.
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Chandrasoma, Nalin, Sivadarshini Pathmanathan et Keith R. Buszek. « A practical, multi-gram synthesis of (±)-herbindole A, (±)-herbindole B, and (±)-herbindole C from a common intermediate via 6,7-indole aryne cycloaddition and Pd(0)-catalyzed cross-coupling reactions ». Tetrahedron Letters 56, no 23 (juin 2015) : 3507–10. http://dx.doi.org/10.1016/j.tetlet.2015.02.064.

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Liu, Baohua, Chunyan Mao, Qiong Hu, Liangliang Yao et Yimin Hu. « Direct methylation and carbonylation of in situ generated arynes via HDDA-Wittig coupling ». Organic Chemistry Frontiers 6, no 15 (2019) : 2788–91. http://dx.doi.org/10.1039/c9qo00621d.

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A high-efficiency HDDA-Wittig coupling strategy for synthesis of fully functionalized benzenes is reported. Direct methylation and carbonylation of aryne intermediates reacted with phosphorus ylides to form the carbonylated 2,3-dihydro-1H-indenes.
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Dong, Yuyang, Michael I. Lipschutz et T. Don Tilley. « Regioselective, Transition Metal-Free C–O Coupling Reactions Involving Aryne Intermediates ». Organic Letters 18, no 7 (24 mars 2016) : 1530–33. http://dx.doi.org/10.1021/acs.orglett.6b00183.

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Nhari, Laila M., Elham N. Bifari, Aisha R. Al-Marhabi, Huda A. Al-Ghamdi, Sameera N. Al-Ghamdi, Fatimah A. M. Al-Zahrani, Khalid O. Al-Footy et Reda M. El-Shishtawy. « Synthesis of Novel Key Chromophoric Intermediates via C-C Coupling Reactions ». Catalysts 12, no 10 (21 octobre 2022) : 1292. http://dx.doi.org/10.3390/catal12101292.

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The fundamentals of Pd-catalyzed Csp2−Csp2 Miyaura borylation, Suzuki cross-coupling, and Stille cross-coupling reactions for a variety of borylated precursors based on phenothiazine (PTZ), phenoxazine (POZ), carbazole (Cz), and quinoxaline (QX) units have been explored. Three palladium-based catalysts were chosen for this study: Pd(PPh3)4, Pd(PPh3)2Cl2, and Pd(dppf)Cl2, applying different reaction conditions. Around 16 desired chromophores were successfully designed and synthesized using C-C cross-coupling reactions in moderate to excellent yields, including PTZ, POZ, and Cz units coupled with QX, indolinium iodide, thienyl, phenyl, or triphenylamine moieties. Additionally, PTZ, POZ, and Cz have been employed in synthesizing various pinacol boronate ester derivatives in good to moderate yields. Interestingly, Pd(dppf)Cl2 was found to be the best catalyst for borylation, and C-C cross-coupling reactions occurred in as little as 30 min, with an excellent yield exceeding 98%. Pd(PPh3)4 and Pd(PPh3)2Cl2 catalyzed the reaction to obtain the desired products in moderate to good yields after a long time (20–24 h). On the other hand, the Suzuki-Miyaura cross-coupling between N-(2-methyl)hexyl carbazole pinacol boronate ester derivative 10c and three halogenated quinoxaline derivatives—4-(3-(5-bromothiophen-2-yl)quinoxalin-2-yl)benzaldehyde (27), 4-(5-(3-(5-bromothiophen-2-yl)quinoxalin-2-yl)thiophen-2-yl)benzaldehyde (30), and 4-(3-chloroquinoxalin-2-yl)benzaldehyde (25) catalyzed by Pd(PPh3)4—afforded three carbazole-quinoxaline chromophores (28, 30, and 31, respectively) in 2–3 h, with good to excellent yields reaching 86%. The electron-deficient QX couplers proved to be coupled efficiently using the Stille coupling reaction, which involves the coupling between electron-rich orgaostannane and electron-deficient halide. The synthesized precursors and desired chromophores were characterized by FTIR, 1H-NMR, 13C-NMR, and HRMS.
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Burt, Liam K., Richard L. Cordiner, Anthony F. Hill, Richard A. Manzano et Jörg Wagler. « The significance of phosphoniocarbynes in halocarbyne cross-coupling reactions ». Chemical Communications 56, no 42 (2020) : 5673–76. http://dx.doi.org/10.1039/d0cc02070b.

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Competent intermediates as well as productive and non-productive tangents have been identified in the catalytic cycle for palladium(0)–copper(i) mediated synthesis of propargylidynes via cross coupling reactions of bromocarbyne complexes with alkynes.
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Tang, Jianting, Leiyang Lv, Xi-Jie Dai, Chen-Chen Li, Lu Li et Chao-Jun Li. « Nickel-catalyzed cross-coupling of aldehydes with aryl halides via hydrazone intermediates ». Chemical Communications 54, no 14 (2018) : 1750–53. http://dx.doi.org/10.1039/c7cc09290c.

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A novel nickel-catalyzed cross-coupling reaction between aldehydes and aryl halides via hydrazone intermediates has been developed. It merges the Wolff–Kishner reduction and classical cross-coupling reactions, thus opening up new routes in designing chemical synthesis.
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Friese, Florian W., et Armido Studer. « New avenues for C–B bond formation via radical intermediates ». Chemical Science 10, no 37 (2019) : 8503–18. http://dx.doi.org/10.1039/c9sc03765a.

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Efficient radical routes to important alkyl and aryl boronic esters have been developed over the past few years. Such reactions are complementary to existing transition-metal catalysed cross coupling processes.
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Zhao, Yin-Na, Yong-Chun Luo, Zhu-Yin Wang et Peng-Fei Xu. « A new approach to access difluoroalkylated diarylmethanes via visible-light photocatalytic cross-coupling reactions ». Chemical Communications 54, no 32 (2018) : 3993–96. http://dx.doi.org/10.1039/c8cc01486h.

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Thèses sur le sujet "Coupling reactions via aryne intermediates"

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Truong, Tan Sang. « Bromanes/Chloranes (cycliques) lambda3-biaryliques : composes hypervalents rares pour la synthese rapide de molecules complexes ». Electronic Thesis or Diss., Strasbourg, 2025. http://www.theses.fr/2025STRAF006.

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Contrairement aux λ3-iodanes diaryliques bien étudiés, la chimie des dérivés λ3-bromane et λ3-chlorane a été rarement explorée en raison de leur synthèse complexe, occultant ainsi les applications potentielles. Nous nous sommes concentrés sur le développement de méthodes de synthèse efficaces pour les λ3-bromanes/chloranes (cyliques) diaryliques, ainsi que sur l'exploration de leur potentiel unique en tant que précurseurs d'arynes novateurs et leur réactivité en tant que réactifs efficace d’arylation. Les intermédiaires aryne, générés à partir de λ3-bromanes/chloranes, ont servi de plateformes synthétiques puissantes et durables pour la construction efficace de structures moléculaires complexes. De plus, l’insertion d'arynes dans les liaisons σ N–Si d’aminosilanes avec des réactifs λ3-bromanes/chloranes (cyliques) diaryliques a permis un accès direct à des dérivés 3-amino-2-silylbiaryls. Des investigations expérimentales mécanistiques, combinées à des calculs DFT, ont été menées pour élucider la réactivité distincte et améliorée des réactifs (cyliques) diaryliques de brome(III) et de chlore(III) dans transformations chimiques
In contrast to well-studied diaryl λ3-iodanes, the chemistry of λ3-bromane and λ3-chlorane congeners has been scarcely explored due to their challenging synthesis, shadowing their potential applications. For this purpose, we focused on developing the practical and efficient synthetic methods for (cyclic) diaryl λ3-bromanes/chloranes, as well as exploring their unique as novel aryne precursors and superior reactivity as enhanced arylating reagents. The aryne intermediates, generated from (cyclic) diaryl λ3-bromanes/chloranes, served as a potent and sustainable synthetic platforms for a straightforward and efficient construction of complex molecular frameworks. In addition, aryne insertion into N–Si σ-bonds of aminosilanes with cyclic diaryl λ3-bromane/chlorane reagents enabled a direct access to 3-amino-2-silylbiaryl derivatives. Experimental mechanistic investigations, combined with DFT calculations, were further conducted to elucidate the distinct and enhanced reactivity of the rarely explored (cyclic) diaryl hypervalent bromine(III) and chlorine(III) reagents in diverse and versatile chemical transformations
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Chapitres de livres sur le sujet "Coupling reactions via aryne intermediates"

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Bayer, Anton, et Uli Kazmaier. « Cross-Coupling Reactions via sπ-Allylmetal Intermediates ». Dans Metal-Catalyzed Cross-Coupling Reactions and More, 925–94. Weinheim, Germany : Wiley-VCH Verlag GmbH & Co. KGaA, 2013. http://dx.doi.org/10.1002/9783527655588.ch12.

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Lambert, Tristan H. « Construction of Alkylated Stereocenters : The Deng Synthesis of (–)-Isoacanthodoral ». Dans Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0042.

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Matthew S. Sigm an at the University of Utah developed (Science 2012, 338, 1455) a redox-relay strategy that allowed for the enantioselective Heck arylation of alcohol 1 with diazo salt 2 to produce γ-arylated aldehyde 4 with high ee. Stephen P. Fletcher at the University of Oxford reported (Nature Chem. 2012, 4, 649) a procedure that utilized alkenes as alkylmetal equivalents for asymmetric conjugate additions, such as in the conversion of cyclohexenone 5 to ketone 7. A catalytic method for the regioselective and highly enantioselective 1,6-addition of alkynes to α, β, γ, δ-unsaturated carbonyls (e.g., 8 to 9) was reported (J. Am. Chem. Soc. 2012, 134, 18936) by Takahiro Nishimura at Kyoto University and Tamio Hayashi at the IMRE in Singapore. Scott E. Schaus at Boston University found (J. Am. Chem. Soc. 2012, 134, 19965) that BINOL 12 catalyzed the enantioselective addition of aryl or vinyl boronates to o-quinone methides, such as that generated from 10 to furnish 13. Elizabeth R. Jarvo at the University of California at Irvine discovered (Angew. Chem. Int. Ed. 2012, 51, 7790) that triarylmethanes such as 15 could be prepared by enantiospecific cross-coupling of diarylmethane ethers, as long as the ether was capable of chelation (e.g., 14). Alternatively, Mary P. Watson at the University of Delaware found (J. Am. Chem. Soc. 2013, 135, 3307) that benzylic pivalates could be enantiospecifically cross-coupled with arylboroxines, as in the conversion of 16 to 17. Yoann Coquerel and Jean Rodriguez at the University of Aix-Marseille found (Org. Lett. 2012, 14, 4686) that β-ketoamides could be directly arylated by reaction with in situ-generated aryne intermediates, such as in the conversion of 18 to 20. A unique approach to the asymmetric formation of acyclic quaternary stereocenters via a carbometalation-oxidation-aldol cascade of alkyne 21 to produce 22 was reported (Nature 2012, 490, 522) by Ilan Marek at the Technion-Israel Institute of Technology. Keiji Maruoka at Kyoto University reported (J. Am. Chem. Soc. 2012, 134, 16068) the first organocatalytic conjugate addition of aldehydes to acrylate esters by making use of amine catalyst 25 and the highly electrophilic fluorinated acrylate 23.
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