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Journal articles on the topic 'Coupling Benzynes'

Author: Grafiati

Published: 6 September 2023

Last updated: 31 July 2025

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1

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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2

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 (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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3

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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4

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 (2011): 247–50. http://dx.doi.org/10.1002/ejoc.201101251.

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5

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 (2012): no. http://dx.doi.org/10.1002/chin.201222064.

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6

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 (2007): 8163–65. http://dx.doi.org/10.1016/j.tetlet.2007.09.092.

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7

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 (2009): 391–94. http://dx.doi.org/10.1002/anie.200804873.

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8

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 (2009): 397–400. http://dx.doi.org/10.1002/ange.200804873.

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9

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 (2005): 2921–24. http://dx.doi.org/10.1021/ol050859r.

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10

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 (2019): 2697–703. http://dx.doi.org/10.1021/acs.joc.9b02874.

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11

Buchwald, Stephen L., Brett T. Watson, Robert T. Lum, and William A. Nugent. "A general method for the preparation of zirconocene complexes of substituted benzynes: in situ generation, coupling reactions, and use in the synthesis of polyfunctionalized aromatic compounds." Journal of the American Chemical Society 109, no. 23 (1987): 7137–41. http://dx.doi.org/10.1021/ja00257a038.

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12

García-López, José-Antonio, and Michael F. Greaney. "Synthesis of biaryls using aryne intermediates." Chemical Society Reviews 45, no. 24 (2016): 6766–98. http://dx.doi.org/10.1039/c6cs00220j.

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13

Welsh, Erin N., Katherine N. Robertson, and Alexander W. H. Speed. "Short syntheses of 1-substituted dibenzothiophene derivatives." Organic & Biomolecular Chemistry 19, no. 9 (2021): 2000–2007. http://dx.doi.org/10.1039/d0ob01839b.

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14

Xia, Wujiong, Xinxin Zhao, Ming Chen, Binbin Huang, Chao Yang, and Yuan Gao. "Photoinduced Cross-Coupling of Amines with 1,2-Diiodobenzene and Its Application in the Synthesis of Carbazoles." Synthesis 50, no. 15 (2018): 2981–89. http://dx.doi.org/10.1055/s-0037-1609444.

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A facile and efficient process for the preparation of various tertiary aminobenzenes and carbazole derivatives via photoinduced cross-coupling of amines with 1,2-diiodobenzene is reported. Mechanistic investigations indicate that the transformation proceeds via nucleophilic addition of an amine to the benzyne intermediate accompanied with a proton transfer process, followed by an oxidative cyclization of the generated diphenylamine to furnish the corresponding carbazole products.

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15

Henderson, Jaclyn L., Andrew S. Edwards, and Michael F. Greaney. "Three-Component Coupling of Benzyne: Domino Intermolecular Carbopalladation." Journal of the American Chemical Society 128, no. 23 (2006): 7426–27. http://dx.doi.org/10.1021/ja0615526.

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16

Bennett, Martin A. "Aryne Complexes of Zerovalent Metals of the Nickel Triad." Australian Journal of Chemistry 63, no. 7 (2010): 1066. http://dx.doi.org/10.1071/ch10198.

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The chemistry of dihapto-aryne complexes of the zerovalent Group 10 metals of general formula [M(η2-aryne)L2] (M = Ni, Pd, Pt; L = various tertiary phosphines) is reviewed, with emphasis on the highly reactive nickel(0) compounds (aryne = benzyne, C6H4; 4,5-difluorobenzyne, 4,5-C6H2F2; 2,3-naphthalyne, 2,3-C10H6; L2 = 2 PEt3, 2 PiPr3, 2 PCy3, dcpe). These can be generated by alkali metal reduction of the appropriate (2-halogenoaryl)nickel(ii) halide precursors, such as [NiX(2-XC6H4)L2], which in turn are accessible by oxidative addition of the 1,2-dihaloarene to nickel(0) precursors such as [N

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17

McGlinchey, Michael J., and Kirill Nikitin. "Palladium-Catalysed Coupling Reactions En Route to Molecular Machines: Sterically Hindered Indenyl and Ferrocenyl Anthracenes and Triptycenes, and Biindenyls." Molecules 25, no. 8 (2020): 1950. http://dx.doi.org/10.3390/molecules25081950.

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Pd-catalysed Stille and Suzuki cross-couplings were used to prepare 9-(3-indenyl)-, 6, and 9-(2-indenyl)-anthracene, 7; addition of benzyne led to the 9-Indenyl-triptycenes, 8 and 9. In 6, [4 + 2] addition also occurred to the indenyl substituent. Reaction of 6 through 9 with Cr(CO)6 or Re2(CO)10 gave their M(CO)3 derivatives, where the Cr or Re was complexed to a six- or five-membered ring, respectively. In the 9-(2-indenyl)triptycene complexes, slowed rotation of the paddlewheel on the NMR time-scale was apparent in the η5-Re(CO)3 case and, when the η6-Cr(CO)3 was deprotonated, the resulting

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18

Jones, Elizabeth P., Peter Jones, Andrew J. P. White, and Anthony G. M. Barrett. "Asymmetric synthesis of quaternary aryl amino acid derivatives via a three-component aryne coupling reaction." Beilstein Journal of Organic Chemistry 7 (November 25, 2011): 1570–76. http://dx.doi.org/10.3762/bjoc.7.185.

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A method was developed for the synthesis of α-alkyl, α-aryl-bislactim ethers in good to excellent yields and high diastereoselectivities, consisting of a facile one-pot procedure in which the aryl group is introduced by means of a nucleophilic addition to benzyne and the alkyl group by alkylation of a resultant benzylic anion. Hydrolysis of the sterically less hindered adducts gave the corresponding quaternary amino acids with no racemization, whereas hydrolytic ring opening gave the corresponding valine dipeptides from bulkier bislactims.

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19

García-López, José-Antonio, Meliha Çetin, and Michael F. Greaney. "Double Heteroatom Functionalization of Arenes Using Benzyne Three-Component Coupling." Angewandte Chemie International Edition 54, no. 7 (2015): 2156–59. http://dx.doi.org/10.1002/anie.201410751.

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20

García-López, José-Antonio, Meliha Çetin, and Michael F. Greaney. "Double Heteroatom Functionalization of Arenes Using Benzyne Three-Component Coupling." Angewandte Chemie 127, no. 7 (2015): 2184–87. http://dx.doi.org/10.1002/ange.201410751.

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21

Wei, Yong-Liang, Yue Li, Yun-Qi Chen, et al. "Pd(II)-NHDC-Functionalized UiO-67 Type MOF for Catalyzing Heck Cross-Coupling and Intermolecular Benzyne–Benzyne–Alkene Insertion Reactions." Inorganic Chemistry 57, no. 8 (2018): 4379–86. http://dx.doi.org/10.1021/acs.inorgchem.7b03271.

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22

Larrosa, Igor, Marianne I. Da Silva, Patricio M. Gómez, et al. "Highly Convergent Three Component Benzyne Coupling: The Total Synthesis ofent-Clavilactone B." Journal of the American Chemical Society 128, no. 43 (2006): 14042–43. http://dx.doi.org/10.1021/ja0662671.

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23

Soorukram, Darunee, Tao Qu, and Anthony G. M. Barrett. "Four-Component Benzyne Coupling Reactions: A Concise Total Synthesis of Dehydroaltenuene B." Organic Letters 10, no. 17 (2008): 3833–35. http://dx.doi.org/10.1021/ol8015435.

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24

Garcia-Lopez, Jose-Antonio, Meliha Cetin, and Michael F. Greaney. "ChemInform Abstract: Double Heteroatom Functionalization of Arenes Using Benzyne Three-Component Coupling." ChemInform 46, no. 25 (2015): no. http://dx.doi.org/10.1002/chin.201525067.

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25

Kan, Steven Z., Young C. Xu, Quan Chen, and Ben S. Freiser. "Coupling reactions of Fe(benzyne)+ and Fe(naphthyne)+ in the gas phase." Journal of Mass Spectrometry 32, no. 12 (1997): 1310–16. http://dx.doi.org/10.1002/(sici)1096-9888(199712)32:12<1310::aid-jms591>3.0.co;2-6.

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26

Frid, Michael, Dolores Pérez, Andrew J. Peat, and Stephen L. Buchwald. "A Combined Zirconocene Benzyne−Palladium Cross-Coupling Route to Substituted Biphenyls and Terphenyls." Journal of the American Chemical Society 121, no. 40 (1999): 9469–70. http://dx.doi.org/10.1021/ja992345r.

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27

Sun, Ruoshui, and Yicheng Wang. "The total synthesis of Wulfenioidin F." Theoretical and Natural Science 44, no. 1 (2024): 123–26. http://dx.doi.org/10.54254/2753-8818/44/20240956.

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Zika virus, an RNA virus that can cause severe damage to the human body, has long lacked an effective drug. Scientists have discovered recently that Wulfenioidin, a plant distributed in southern China, contains a compound in its root that holds the potential to become an anti-Zika drug. Through extraction, multiple kinds of Wulfenioidin were discovered and their structures were characterized through various spectroscopic methods. However, there isnt a total synthesis pathway for Wulfenioidin. This essay focuses on Wulfenioidin F and provides a full synthesis pathway for the molecule. The route

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28

Retbøll, Mikael, Alison J. Edwards, A. David Rae, Anthony C. Willis, Martin A. Bennett, and Eric Wenger. "Preparation of Benzyne Complexes of Group 10 Metals by Intramolecular Suzuki Coupling ofortho-Metalated Phenylboronic Esters: Molecular Structure of the First Benzyne-Palladium(0) Complex." Journal of the American Chemical Society 124, no. 28 (2002): 8348–60. http://dx.doi.org/10.1021/ja0264091.

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29

Pineschi, Mauro, Francesco Berti, Paolo Crotti, and Giulio Cassano. "Copper-Catalyzed Arylation of Alkenyl Aziridines via Three-Component Coupling Reaction involving Alkynes and Benzyne." Synlett 23, no. 17 (2012): 2463–68. http://dx.doi.org/10.1055/s-0031-1290467.

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30

Buchwald, Stephen L., Ann Sayers, Brett T. Watson, and John C. Dewan. "The zirconocene induced coupling of benzyne with nitriles: Synthesis, structure and reactions of novel azametallacyclopentenes." Tetrahedron Letters 28, no. 28 (1987): 3245–48. http://dx.doi.org/10.1016/s0040-4039(00)95483-2.

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31

Frid, Michael, Dolores Perez, Andrew J. Peat, and Stephen L. Buchwald. "ChemInform Abstract: A Combined Zirconocene Benzyne-Palladium Cross-Coupling Route to Substituted Biphenyls and Terphenyls." ChemInform 31, no. 4 (2010): no. http://dx.doi.org/10.1002/chin.200004104.

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32

Bender, Christopher O., René T. Boeré, Peter W. Dibble, and Ryan T. McKay. "Structures of the 2:1 adducts of benzyne with 2-methylanisole and benzene." Canadian Journal of Chemistry 85, no. 7-8 (2007): 461–65. http://dx.doi.org/10.1139/v07-058.

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The 2:1 adduct of benzyne with 2-methylanisole is shown to have the bisbenzotricyclic structure 6,6a,11,11a-tetrahydro-5-methoxy-6-methyl-5,6,11-metheno-5H-benzo[a]fluorene by a single-crystal X-ray diffraction study (C20H18O: Pca21, a = 15.0497(17), b = 9.87783(11), c = 9.6846(11); Z = 4; 1672 data points, R1 = 0.0325). This structure is compared to an unpublished crystal structure of the parent hydrocarbon 6,6a,11,11a-tetrahydro-5,6,11-metheno-5H-benzo[a]fluorene, C18H14. Both structures have also been computed by DFT methods at the B3LYP/6-311(d,p) level of theory. Bond distances and angles

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33

Kotha, Raghavendhar R., Ravikiran Yerabolu, Duanchen Ding, et al. "Spin–Spin Coupling Between Two meta ‐Benzyne Moieties In a Quinolinium Tetraradical Cation Increases Their Reactivities." Chemistry – A European Journal 25, no. 17 (2019): 4472–77. http://dx.doi.org/10.1002/chem.201806096.

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34

Aseman, Marzieh Dadkhah, Christina A. Roselli, and Michel R. Gagné. "Promoting C–C Bond Coupling of Benzyne and Methyl Ligands in Electron-Deficient (triphos)Pt–CH3+ Complexes." Organometallics 34, no. 12 (2015): 2707–9. http://dx.doi.org/10.1021/acs.organomet.5b00121.

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35

Berti, Francesco, Paolo Crotti, Giulio Cassano, and Mauro Pineschi. "ChemInform Abstract: Copper-Catalyzed Arylation of Alkenyl Aziridines via Three-Component Coupling Reaction Involving Alkynes and Benzyne." ChemInform 44, no. 9 (2013): no. http://dx.doi.org/10.1002/chin.201309062.

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36

Nagaki, Aiichiro, Daisuke Ichinari, and Jun-ichi Yoshida. "Three-Component Coupling Based on Flash Chemistry. Carbolithiation of Benzyne with Functionalized Aryllithiums Followed by Reactions with Electrophiles." Journal of the American Chemical Society 136, no. 35 (2014): 12245–48. http://dx.doi.org/10.1021/ja5071762.

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37

Dupuis, Laurence, Nadine Pirio, Philippe Meunier, Alain Igau, Bruno Donnadieu, and Jean-Pierre Majoral. "Zirconocen–Benzyme-Mediated Intramolecular Coupling of Bis(alkynyl)phosphane: A Way to Mono- and Tricyclic 1,2-Dihydrophosphetes." Angewandte Chemie International Edition in English 36, no. 9 (1997): 987–89. http://dx.doi.org/10.1002/anie.199709871.

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38

Helgaker, Trygve, and Michał Jaszuński. "Density-Functional and Coupled-Cluster Singles-and-Doubles Calculations of the Nuclear Shielding and Indirect Nuclear Spin−Spin Coupling Constants of o-Benzyne." Journal of Chemical Theory and Computation 3, no. 1 (2006): 86–94. http://dx.doi.org/10.1021/ct600234n.

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39

Nettles, Shawn M., and Jeffrey L. Petersen. "Synthesis and structural characterization of [(C5H4)SiMe2(N-t-Bu)]Ti[(o-C6H4)C(Ph)C(Ph)], generated via an alkyne-Ti benzyne coupling reaction." Journal of Organometallic Chemistry 692, no. 21 (2007): 4654–60. http://dx.doi.org/10.1016/j.jorganchem.2007.06.019.

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40

Zhang, Yajuan, Jie Dong, Yu Lei, Lingli Zong, Ke Zhang, and Yimin Hu. "High Regioselectivity Ferrocenyl Cyclohexene/Cyclopentene Ferrocene Isomerization through Benzynes Transfer Coupling." Organic Chemistry Frontiers, 2023. http://dx.doi.org/10.1039/d2qo01836e.

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High regioselectivity Ferrocenyl cyclohexene/cyclopentene isomerization through hexadehydro-Diels-Alder (HDDA) benzyne transfer coupling was developed. The tetraynes result in the formation of an aryne through HDDA reaction which is then in situ...

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41

Dong, Haiyan, Xinran Ding, and Chuan Wang. "Nickel-Catalyzed Cross-Electrophile [2+4] Annulation of Benzynes." Synlett, January 9, 2025. https://doi.org/10.1055/a-2513-8549.

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Cross-electrophile coupling (XEC) reactions have emerged as a powerful tool for C‒C bond formation, while annulation employ-ing arynes provides unique approaches to polycyclic arenes. Herein, we report a nickel-catalyzed cross-electrophile [2+4] annulation using benzyne and 1-bromo-2-(2-chlorovinyl)arenes as a C-2 and a C-4 synthon, respectively. This proof-of-concept study not only provides a new method to synthesize multi-substituted phenanthrenes but also substantiates the feasibility of merging XEC reaction and aryne chemistry.

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42

Jeganmohan, Masilamani, Sivakolundu Bhuvaneswari, and Chien-Hong Cheng. "ChemInform Abstract: A Cooperative Copper- and Palladium-Catalyzed Three-Component Coupling of Benzynes, Allylic Epoxides, and Terminal Alkynes." ChemInform 40, no. 20 (2009). http://dx.doi.org/10.1002/chin.200920062.

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43

Yang, Yun-Yun, Wang-Ge Shou, and Yan-Guang Wang. "ChemInform Abstract: Tandem Coupling Reactions of Benzynes and 1,3-Diones: A Novel Synthesis of 2,2-Diphenyl-1,3-diones." ChemInform 39, no. 9 (2008). http://dx.doi.org/10.1002/chin.200809108.

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44

Jayanth, Thiruvellore Thatai, Masilamani Jeganmohan, and Chien-Hong Cheng. "Highly Efficient Route to o-Allylbiaryls via Palladium-Catalyzed Three-Component Coupling of Benzynes, Allylic Halides, and Aryl Organometallic Reagents." ChemInform 36, no. 45 (2005). http://dx.doi.org/10.1002/chin.200545110.

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45

BUCHWALD, S. L., B. T. WATSON, R. T. LUM, and W. A. NUGENT. "ChemInform Abstract: A General Method for the Preparation of Zirconocene Complexes of Substituted Benzynes: in situ Generation, Coupling Reactions, and Use in the Synthesis of Polyfunctionalized Aromatic Compounds." ChemInform 19, no. 10 (1988). http://dx.doi.org/10.1002/chin.198810300.

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46

Sureshbabu, Popuri, and Priyanka Chaudhary. "Synthesis of Indazole Scaffolds from Arynes and Suitable Coupling Partners - A Brief Review." Mini-Reviews in Organic Chemistry 21 (July 31, 2024). http://dx.doi.org/10.2174/0118756298321262240719103850.

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Transition metal-free annulation/cascade reactions have been embraced as a powerful synthetic tool to access carbo/heterocyclic molecules. Among them, benzyne chemistry gained significant interest due to the formation of diverse functionalized arenes via unusual carboncarbon (C-C) or carbon-heteroatom (C-O, C-N, C-S) bond-formation under different reaction conditions. In this review, few dynamic methods have been documented to construct the synthetically and pharmaceutically valuable indazole scaffolds using benzyne precursor and various other coupling partners. In this mini-review, we have de

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47

Welsh, Erin N., Katherine N. Robertson, and Alexander W. H. Speed. "Gram-Scale Synthesis of the N-Phenyl Phenothiazine Photocatalyst by Benzyne Addition." Canadian Journal of Chemistry, August 3, 2022. http://dx.doi.org/10.1139/cjc-2022-0139.

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N-phenyl phenothiazine is one of the most reducing photoredox catalysts. Its synthesis commonly requires transition metal catalyzed cross-coupling reactions. Here we show the syntheses of four aryl phenothiazines via a benzyne route, including a multi-gram scale synthesis of N-phenyl phenothiazine. While yields are modest, the simplicity, low cost, and lack of requirement for cross-coupling catalysts in this synthesis will be attractive to users of this photocatalyst.

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48

Henderson, Jaclyn L., Andrew S. Edwards, and Michael F. Greaney. "Three-Component Coupling of Benzyne: Domino Intermolecular Carbopalladation." ChemInform 37, no. 43 (2006). http://dx.doi.org/10.1002/chin.200643107.

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49

Larrosa, Igor, Marianne I. Da Silva, Patricio M. Gomez, et al. "Highly Convergent Three-Component Benzyne Coupling: The Total Synthesis of ent-Clavilactone B." ChemInform 38, no. 11 (2007). http://dx.doi.org/10.1002/chin.200711207.

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50

Arndtsen, Bruce A., Karina S. Wong та Mohammad Ghanbari. "Design of a Modular, Palladium-Catalyzed Carbonylative Synthesis of Pyrido[2,1-α]isoindoles via Benzyne 1,3-Dipolar Cycloaddition". Chemical Communications, 2025. https://doi.org/10.1039/d4cc06483f.

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We report a palladium catalyzed, multicomponent synthesis of pyrido[2,1-α]isoindoles via carbonylative coupling of imines and 2-bromopyridines to form mesoionic dipoles, followed by cycloaddition with in situ generated arynes. This one-pot...

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