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Academic literature on the topic 'Coupling Benzynes'

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Published: 6 September 2023

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Journal articles on the topic "Coupling Benzynes"

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Ikawa, Takashi, Hideki Kaneko, Shigeaki Masuda, Erika Ishitsubo, Hiroaki Tokiwa, and Shuji Akai. "Trifluoromethanesulfonyloxy-group-directed regioselective (3 + 2) cycloadditions of benzynes for the synthesis of functionalized benzo-fused heterocycles." Organic & Biomolecular Chemistry 13, no. 2 (2015): 520–26. http://dx.doi.org/10.1039/c4ob01627k.

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Bao, Zhicheng, Chaoqiang Wu, and Jianbo Wang. "Palladium-Catalyzed Three-Component Coupling of Benzynes, Benzylic/Allylic Bromides and 1,1-Bis[(pinacolato)boryl]methane." Catalysts 13, no. 1 (January 5, 2023): 126. http://dx.doi.org/10.3390/catal13010126.

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We report herein a palladium-catalyzed three-component cross-coupling reaction of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, benzylic/allylic bromides and 1,1-bis[(pinacolato)boryl]methane. The reaction, which affords benzyl boronates as the products, represents the first example of using 1,1-bis[(pinacolato)boryl]methane in a cross-coupling reaction involving benzyne species.
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Lu, Tianhao, Yong Shen, Min Wang, Zibing Zhang, Shijun Li, and Chunsong Xie. "Aerobic Cu-catalyzed oxidative 1 : 2 coupling of benzynes with terminal alkynes." Chemical Communications 56, no. 59 (2020): 8214–17. http://dx.doi.org/10.1039/d0cc03150j.

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Lee, Yi-Hsien, Yen-Chung Chen, and Jen-Chieh Hsieh. "Pyridine-Catalyzed Double C-N Coupling Reaction of an Isocyanate with Two Benzynes." European Journal of Organic Chemistry 2012, no. 2 (November 21, 2011): 247–50. http://dx.doi.org/10.1002/ejoc.201101251.

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Lee, Yi-Hsien, Yen-Chung Chen, and Jen-Chieh Hsieh. "ChemInform Abstract: Pyridine-Catalyzed Double C-N Coupling Reaction of an Isocyanate with Two Benzynes." ChemInform 43, no. 22 (May 3, 2012): no. http://dx.doi.org/10.1002/chin.201222064.

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Yang, Yun-Yun, Wang-Ge Shou, and Yan-Guang Wang. "Tandem coupling reactions of benzynes and 1,3-diones: a novel synthesis of 2,2-diphenyl-1,3-diones." Tetrahedron Letters 48, no. 46 (November 2007): 8163–65. http://dx.doi.org/10.1016/j.tetlet.2007.09.092.

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Jeganmohan, Masilamani, Sivakolundu Bhuvaneswari, and Chien-Hong Cheng. "A Cooperative Copper- and Palladium-Catalyzed Three-Component Coupling of Benzynes, Allylic Epoxides, and Terminal Alkynes." Angewandte Chemie International Edition 48, no. 2 (January 2, 2009): 391–94. http://dx.doi.org/10.1002/anie.200804873.

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Jeganmohan, Masilamani, Sivakolundu Bhuvaneswari, and Chien-Hong Cheng. "A Cooperative Copper- and Palladium-Catalyzed Three-Component Coupling of Benzynes, Allylic Epoxides, and Terminal Alkynes." Angewandte Chemie 121, no. 2 (January 2, 2009): 397–400. http://dx.doi.org/10.1002/ange.200804873.

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Jayanth, Thiruvellore Thatai, Masilamani Jeganmohan, and Chien-Hong Cheng. "Highly Efficient Route too-Allylbiaryls via Palladium-Catalyzed Three-Component Coupling of Benzynes, Allylic Halides, and Aryl Organometallic Reagents." Organic Letters 7, no. 14 (July 2005): 2921–24. http://dx.doi.org/10.1021/ol050859r.

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Das, Eshani, and Amit Basak. "Regioselective Synthesis of Benzo-Fused Tetrahydroisoquinoline-Based Biaryls through a Tandem One-Pot Halogenation of p-Benzynes from Enediynes and Suzuki-Miyaura Coupling." Journal of Organic Chemistry 85, no. 4 (December 27, 2019): 2697–703. http://dx.doi.org/10.1021/acs.joc.9b02874.

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Dissertations / Theses on the topic "Coupling Benzynes"

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Henderson, Jaclyn. "Benzyne in synthesis : a search for palladium catalysed three-component couplings." Thesis, University of Edinburgh, 2008. http://hdl.handle.net/1842/4868.

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It is over 100 years since scientists first postulated the existence of arynes as reactive intermediates. Their use in organic synthesis is now well-established and investigations into novel methods for their generation and utility in carbon-carbon bond forming reactions continue to this day. In 1983 Kobayashi and co-workers introduced a novel method of generating benzyne under mild conditions, using a fluoride induced decomposition of 2-(trimethylsilyl)phenyl triflate 1. This development has opened the door to employing arynes in a variety of transitionmetal mediated carbon-carbon bond forming processes. Intermolecular carbopalladation, in particular, stands out as a powerful methodology for the construction of diverse 1,2-functionalised arenes through multi-component coupling processes. Initial benzyne carbopalladation with an organopalladium species produces the arylpalladium intermediate 3, which can then undergo a second coupling to any one of the vast numbers of nucleophiles that have been demonstrated to work in palladium cross coupling. Presented herein are investigations towards the realisation of such methodology. Initial efforts focussed on its application to the Heck reaction, using acryates as the nucleophilic component. The chemistry has been developed to incorporate a variety of organo-halides in order to generate a variety of molecular architectures; the resultant 1,2-substituted diaryls being useful in the synthesis of both natural products and medicinal chemistry targets. Following successful development of the Heck reaction, investigations of other palladium catalysed couplings were also undertaken, in particular the Buchwald reaction. Initial mechanistic studies are also discussed.
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Pintori, Didier Gil. "Novel benzyne insertion reactions & medium-ring synthesis by oxidative C-H coupling." Thesis, University of Edinburgh, 2011. http://hdl.handle.net/1842/5669.

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This thesis is divided into two main chapters, which are focused on two separated and uncorrelated research areas. The first part of this thesis is dedicated to the research I carried out in benzyne chemistry and the second part is focused on catalytic C-H bond activation. In the first place, a novel insertion reaction of arynes into the nitrogen-carbonyl σ-bond of amides has been investigated as a rapid and powerful approach for the preparation of valuable ortho-disubstituted arenes. Readily available aromatic amides undergo smooth insertion when treated with O-triflatophenyl silane aryne precursors, producing versatile anthranilic derivatives in good to excellent yields. The process is entirely metal-free and has been expanded to the synthesis of biologically active heterocycles such as acridones and acridines. Secondly, the synthesis of medium-sized ring systems by intramolecular oxidative CH bond coupling has been explored. Despite the abundance of biologically active natural products featuring mediumsized rings, the synthesis of such ring systems using classical synthetic routes faces many challenges and has led to a dearth of medium ring compounds in medicinal chemistry. In contrast to the more facile 5-membered ring synthesis by oxidative C-H coupling, medium ring synthesis has not been previously reported using this approach. The chemistry, which requires zero pre-functionalisation of the substrates, is catalysed by palladium and has been exemplified using heteroaromatic substrates at the core of numerous biologically active molecules. The mechanism of the reaction has also been studied and a catalytic cycle has been proposed.
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Jen-Chieh, Hsieh. "Application of Nickel Complexes on the Coupling Reactions and Annulations involving Benzyne, Isocyanate and 1,2-Diiodobenzene Derivatives." 2006. http://www.cetd.com.tw/ec/thesisdetail.aspx?etdun=U0016-1303200709301533.

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Hsieh, Jen-Chieh, and 謝仁傑. "Application of Nickel Complexes on the Coupling Reactions and Annulations involving Benzyne, Isocyanate and 1,2-Diiodobenzene Derivatives." Thesis, 2006. http://ndltd.ncl.edu.tw/handle/20375115204749616358.

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博士
國立清華大學
化學系
94
The thesis describes dipolar and nickel-catalyzed organic synthesis leading to coupling and cyclization of heterocyclic compounds. It is subdivided into four topics in four chapters. The first chapter describes nickel-catalyzed cyclization of aryne precursors with allene and diyne derivatives resulting in the formation of 9,10-dihydrophenanthrene and naphthalene derivatives in moderate to excellent yields. The second chapter extends the aryne precursors to precede 1,3-dipolar cycloaddition and coupling reaction with azide and isocyanate derivatives to form benzotriazole and diphenylamine derivatives in good to excellent yields. The third chapter deals with reaction of isocyanates with β-iodobenzoate and halobenzene derivatives to form imides and amides. The fourth chapter consists of cycloaddition of 1,2-dihalidearenes with alkynes and diynes to form 1,2,3,4-tetrasubstituted naphthalene derivatives. The first chapter describes the nickel-catalyzed cycloaddition of arynes with allenes and diynes. The arynes could be proceeded cycloaddition with allenes and diynes in the presence of Ni(dppe)Br2, zinc powder and cesium fluoride in acetonitrile at 80 oC to afford the corresponding phenanthrene and naphthalene derivatives in moderate to excellent yields. The phenanthrene derivatives give high regio-, stereo- and chemo selectivity; in contract the naphthalene derivatives afford excellent functional group and fused ring size tolerance. The mechanism of these two reactions is through the intermediate of nickelacyclopentadiene by Ni(0) complex with two molecules of triple bonds, followed by insertion of another one and reductive elimination to form the corresponding products. The second chapter describes the coupling reaction of arynes with azides and isocyanates. The arynes undergo the 1,3-dipolar cycloaddition with azides to form the 1H-benzo[d][1,2,3]triazole derivatives in good to excellent yields with high functional groups tolerance. The arynes could also precede the very unique fluoride promoted coupling reaction with isocyanates in moderate to good yields. The third chapter describes the nickel-catalyzed cycloaddition and coupling reaction of isocyanates with β-iodiesters and arylhalide. In the presence of NiBr2(dppe), additional dppe and zinc powder in acetonitrile at 80 oC, the coupling reaction of isocyanates with β-iodiesters and arylhalide could be succeed to proceed and afford the corresponding imide and amide derivatives in moderate to excellent yields. The reaction of forming imides shows the excellent functional group tolerance, however, the reaction of forming amides reveals the lower yields with limited cases. The fourth chapter describes the nickel-catalyzed cycloaddition of 1,2-dihaloarenes with alkynes and diynes. The 1,2-dihaloarenes undergo cycloaddition with alkynes and diynes in the presence of Ni(dppe)Br2, additional dppe and zinc powder in acetonitrile at 100 oC to afford the corresponding 1,2,3,4-tetra substituted naphthalene products in moderate to excellent yields. Variou alkynes and diynes react with 1,2-dihaloarene derivatives to give good functional group tolerance. The mechanism is proposed by the oxidative addition first, then insertion of a triple bond and coupling with another carbon-halide bond to form the intermediate of nickelacyclobenzopentene. Finally, another triple inserts to the nickel complex and proceeds reductive elimination to afford the corresponding naphthalene products.
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Book chapters on the topic "Coupling Benzynes"

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Taber, Douglass. "Synthesis of Substituted Benzenes: The Carter Synthesis of Siamenol." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0062.

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Tosylates are among the least expensive, but also among the least reactive toward Pd(0) oxidative addition, of aryl sulfonates. Jie Wu of Fudan University has now devised conditions (J. Org. Chem. 2007, 72, 9346) for the Pd-catalyzed coupling of aryl tosylates such as 1 with arene trifluoroborates. Kei Manabe of RIKEN has found (Organic Lett. 2007, 9, 5593) that an ortho OH activates an adjacent Cl for Pd-mediated coupling, allowing the conversion of 4 to 6 . Philippe Uriac and Pierre van de Weghe of the Université de Rennes I have developed (Organic Lett. 2007, 9, 3623) conditions for the catalytic acylation of aryl halides with alkenyl acetates such as 8. Multi-component coupling lends itself well to diversity-oriented synthesis. As illustrated by the combination of 10 with 11 and 12 to give 13 reported (Organic Lett. 2007, 9, 5589) by Michael F. Greaney of the University of Edinburgh, benzynes can do double addition with high regiocontrol. For other recent references to unsymmetrical double additions to arynes, see Angew.Chem. Int. Ed. 2007, 46, 5921; Chem. Commun. 2007, 2405; and J. Am. Chem. Soc. 2006, 128, 14042. C-H functionalization of arenes is of increasing importance. John F. Hartwig of the University of Illinois has described (Organic Lett. 2007, 9, 757; 761) improved conditions for Ir-catalyzed meta borylation, and conditions for further coupling of the initial borate 16 to give amines such as 17. Lei Liu and Qing-Xiang Guo of the University of Science and Technology, Hefei have found (Tetrahedron Lett. 2007, 48, 5449) that oxygen can be used as the stoichiometric oxidant in the Pd-catalyzed functionalization of H’s ortho to anilides. Two other research groups (J. Am. Chem. Soc. 2007, 129, 6066; Angew. Chem. Int. Ed. 2007, 46, 5554; J. Org. Chem. 2007, 72, 7720) reported advances in this area. In a close competition, Jin-Quan Yu, now at Scripps/La Jolla (J. Am. Chem. Soc. 2007, 129, 3510) and Olafs Daugulis of the University of Houston (J. Am. Chem. Soc. 2007, 129, 9879) both reported that a carboxyl group can activate an ortho H for direct functionalization.
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Taber, Douglass F. "Substituted Benzenes: The Kirsch Synthesis of Cybrodol." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0063.

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Stephen L. Buchwald of MIT established (J. Am. Chem. Soc. 2010, 132, 14076) a Pd-catalyzed protocol for conversion of an aryl triflate 1 to the halide 2. Jie Wu of Fudan University prepared (Tetrahedron Lett. 2010, 51, 6646) aromatic halides from the corresponding carboxylic acids. Yong-Chua Teo of Nanyang Technological University described (Tetrahedron Lett . 2010, 51, 3910) the Mn-mediated conversion of 3 to 5, suggesting a benzyne intermediate. Takanori Shibata of Waseda University effected (Synlett 2010, 2601) the direct Ru-mediated coupling of aryl halides with amines, and Paul Helquist of the University of Notre Dame prepared (J. Org. Chem. 2010, 75, 4887) anilines by coupling aryl halides with NaN3 . Chao-Jun Li of McGill University devised (Tetrahedron Lett. 2010, 51, 5486) the Pd-catalyzed decarbonylative Heck coupling of 6 with 7 to give 8. Mats Larhed of Uppsala University showed (Angew. Chem. Int. Ed. 2010, 49, 7733) that Pd could also catalyze the decarboxylative coupling of an aromatic acid 9 with a nitrile to give the ketone 10. Dennis G. Hall of the University of Alberta found (Tetrahedron Lett. 2010, 51, 4256) that an areneboronic acid could promote the Zr-catalyzed ortho condensation of a phenol 11 with an aldehyde, leading to 12, which could then be carried on to a range of other products. Professor Hall also showed (Angew. Chem. Int. Ed. 2010, 49, 2883) that areneboronic acids are stable to many standard organic transformations, and that the product boronic acids can be readily purified by extraction into sorbitol/Na2CO3. Professor Buchwald reported (J. Am. Chem. Soc. 2010, 132, 14073) an optimized source of Pd for the Suzuki-Miyaura coupling, allowing the room-temperature participation even of unstable boronic acids such as 13. Wing-Yiu Yu of the Hong Kong Polytechnic University observed (J. Am. Chem. Soc. 2010, 132, 12862) that 17 was an effective donor for the Pd-catalyzed ortho C-H amination of 16. Nicholas C. O. Tomkinson of Cardiff University uncovered (Synlett 2010, 2471) the facile rearrangement of 19 to 20. Professor Buchwald described (J. Am. Chem. Soc. 2010, 132, 9990) the coupling of 21, prepared from the aryl halide, with 22 to give the benzofuran 23.
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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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Taber, Douglass F. "Developments in Flow Chemistry." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0017.

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Klavs S. Jensen of MIT showed (Angew. Chem. Int. Ed. 2014, 53, 470) that “batch” kinetics could be developed in flow by online IR analysis and continuous control. Professor Jensen also demonstrated (Org. Process Res. Dev. 2014, 18, 402) the contin­uous flow production of an active pharmaceutical product, the direct renin inhibitor aliskiren, over two steps and two crystallizations, starting from two advanced interme­diates. Michael Werner and Rainer E. Martin of Hoffmann-La Roche AG Basel com­bined (Angew. Chem. Int. Ed. 2014, 53, 1704) flow synthesis with a flow-based bioassay to develop structure–activity relationships for a series of β-secretase inhibitors. Carlos Mateos of Lilly S. A. and C. Oliver Kappe of the University of Graz used (J. Org. Chem. 2014, 79, 223) flow photolysis to promote the bromination of 1 to 2. Alessandro Palmieri of the University of Camerino and Stefano Protti of the University of Pavia added (Adv. Synth. Catal. 2014, 356, 753) the aldehyde 3 to the acceptor 4 to give, after in-flow reduction, the lactone 5. Peter H. Seeberger of the Max Planck Institute Mühlenberg showed (Org. Lett. 2014, 16, 1794) that the tum­bling action of flow photolysis made the production of 7 by the unlinking of 6 from the polymer bead particularly efficient. Enzymes can also be used under flow conditions. Jörg Pietruszka of the Heinrich-Heine-Universität Düsseldorf employed (Adv. Synth. Catal. 2014, 356, 1007) com­mercial laccase to prepare 10 by coupling 8 with 9. Gas–liquid mixing under flow conditions can also be effective. Núria López of ICIQ Catalonia and Javier Pérez-Ramírez of ETH Zurich developed (Chem. Eur J. 2014, 20, 5926) conditions for the selective hydrogenation of an alkyne 11 to the cis alkene 12. Jun-ichi Yoshida of Kyoto University trapped (Chem. Eur J. 2014, 20, 7931) the inter­mediate organolithium from 13 with CO₂ to give a carboxylate that was carried on to the purifiable O-Su ester 14, ready for further coupling. Timothy F. Jamison, also of MIT, prepared (Angew. Chem. Int. Ed. 2014, 53, 3353) the amino phenol 17 by add­ing the chloromagnesium amide from 16 to the intermediate benzyne from 15, then oxidizing the product with air.
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