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Journal articles on the topic 'Coupling Benzynes'

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Published: 6 September 2023

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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 (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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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 (November 21, 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 (May 3, 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 (November 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 (January 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 (January 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 (July 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 (December 27, 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 (November 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 (May 8, 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 (June 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 [Ni(1,5-COD)2]. The X-ray structure of [Ni(η2-C6H4)(dcpe)] shows that this compound is a typical 16-electron Ni(0) (3d10) species in which benzyne acts as a 2π-electron donor. Several unusual organonickel compounds derived from [Ni(η2-4,5-C6H2F2)(PEt3)2] have been isolated recently, including [Ni2(μ-η2:η2-4,5-C6H2F2)(PEt3)4], in which a 4π-electron donor 4,5-difluorobenzyne is located at right-angles to a pair of nickel atoms. Free benzyne can be intercepted by both [Ni(η2-C2H4)(dcpe)] and [Pt(η2-C2H4)(PPh3)2], but the resulting benzyne complexes rapidly insert benzyne to give the appropriate η1:η1-2,2′-biphenylyl complexes. [Pt(η2-C6H4)(PPh3)2] also undergoes rapid ortho-metallation to give [PtPh(2-C6H4PPh2)(PPh3)]. However, a trapping reaction has been used to make the first 1,4-benzdiyne complex, [{Ni(dcpe)2}2(μ-η2:η2-1,4-C6H2)] by treatment of the 4-fluorobenzyne complex [Ni(η2-4-FC6H3)(dcpe)] with LiTMP. The use of alkali metals in the preparation of the η2-benzyne complexes is avoided in a more recently developed procedure, which starts from (2-bromophenyl)boronic acid, and is based on Suzuki–Miyaura coupling. This procedure has made accessible for the first time an aryne complex of palladium(0), [Pd(η2-C6H4)(PCy3)2], and the labile nickel(0) complex [Ni(η2-C6H4)(PPh3)2]. The aryne-nickel(0) complexes Ni(η2-aryne)L2 (L2 = 2 PEt3, dcpe) undergo sequential insertions into the aryne-metal bond with unsaturated molecules, such as CO, C2F4, substituted alkynes, substituted diynes, alkynylphosphines, and alkynyl thioethers, often with considerable regioselectivity. After the reductive elimination of two nickel-carbon σ-bonds, a variety of interesting polycyclic compounds can be obtained.

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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 (April 22, 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 haptotropic shift of the metal tripod onto the five-membered ring also blocked paddlewheel rotation, thus functioning as an organometallic molecular brake. Suzuki coupling of ferrocenylboronic acid to mono- or dibromoanthracene yielded the ferrocenyl anthracenes en route to the corresponding triptycenes in which stepwise hindered rotations of the ferrocenyl groups behaved like molecular dials. CuCl2-mediated coupling of methyl- and phenyl-indenes yielded their rac and meso 2,2′-biindenyls; surprisingly, however, the apparently sterically crowded rac 2,2′-Bis(9-triptycyl)biindenyl functioned as a freely rotating set of molecular gears. The predicted high rotation barrier in 9-phenylanthracene was experimentally validated via the Pd-catalysed syntheses of di(3-fluorophenyl)anthracene and 9-(1-naphthyl)-10-phenylanthracene.

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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 (January 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 (January 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, Ying Dong, Jia-Jia Yao, Xin-Yue Han, and Yu-Bin Dong. "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 (April 4, 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, Peter Hannen, Eunjung Ko, Steven R. Lenger, Simon R. Linke, Andrew J. P. White, Donna Wilton, and Anthony G. M. Barrett. "Highly Convergent Three Component Benzyne Coupling: The Total Synthesis ofent-Clavilactone B." Journal of the American Chemical Society 128, no. 43 (November 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 (September 4, 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 (June 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 (December 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 (October 1999): 9469–70. http://dx.doi.org/10.1021/ja992345r.

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27

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 (July 2002): 8348–60. http://dx.doi.org/10.1021/ja0264091.

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28

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 (September 21, 2012): 2463–68. http://dx.doi.org/10.1055/s-0031-1290467.

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29

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 (January 1987): 3245–48. http://dx.doi.org/10.1016/s0040-4039(00)95483-2.

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30

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 (June 11, 2010): no. http://dx.doi.org/10.1002/chin.200004104.

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31

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 (July 1, 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 between the solid-state measurements and gas-phase calculations are found to agree well; average deviations are well below 1%. The 1H NMR spectra show surprisingly small 3JHH couplings in the central tricyclic cage, but can be assigned using 2D spectroscopy.Key words: Hydrocarbon cages, strained rings, cyclopropane, X-ray crystallography, NMR.

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32

Kotha, Raghavendhar R., Ravikiran Yerabolu, Duanchen Ding, Lucas Szalwinski, Xin Ma, Ashley Wittrig, John Kong, John J. Nash, and Hilkka I. Kenttämaa. "Spin–Spin Coupling Between Two meta ‐Benzyne Moieties In a Quinolinium Tetraradical Cation Increases Their Reactivities." Chemistry – A European Journal 25, no. 17 (February 25, 2019): 4472–77. http://dx.doi.org/10.1002/chem.201806096.

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33

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 (June 2, 2015): 2707–9. http://dx.doi.org/10.1021/acs.organomet.5b00121.

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34

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 (February 26, 2013): no. http://dx.doi.org/10.1002/chin.201309062.

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35

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 (August 25, 2014): 12245–48. http://dx.doi.org/10.1021/ja5071762.

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36

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 (May 16, 1997): 987–89. http://dx.doi.org/10.1002/anie.199709871.

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37

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 (November 22, 2006): 86–94. http://dx.doi.org/10.1021/ct600234n.

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38

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 (October 2007): 4654–60. http://dx.doi.org/10.1016/j.jorganchem.2007.06.019.

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39

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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40

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 (May 19, 2009). http://dx.doi.org/10.1002/chin.200920062.

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41

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 (February 26, 2008). http://dx.doi.org/10.1002/chin.200809108.

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42

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 (November 8, 2005). http://dx.doi.org/10.1002/chin.200545110.

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43

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 (March 8, 1988). http://dx.doi.org/10.1002/chin.198810300.

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44

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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45

Henderson, Jaclyn L., Andrew S. Edwards, and Michael F. Greaney. "Three-Component Coupling of Benzyne: Domino Intermolecular Carbopalladation." ChemInform 37, no. 43 (October 24, 2006). http://dx.doi.org/10.1002/chin.200643107.

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46

Larrosa, Igor, Marianne I. Da Silva, Patricio M. Gomez, Peter Hannen, Eunjung Ko, Steven R. Lenger, Simon R. Linke, Andrew J. P. White, Donna Wilton, and Anthony G. M. Barrett. "Highly Convergent Three-Component Benzyne Coupling: The Total Synthesis of ent-Clavilactone B." ChemInform 38, no. 11 (March 13, 2007). http://dx.doi.org/10.1002/chin.200711207.

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47

Soorukram, Darunee, Tao Qu, and Anthony G. M. Barrett. "ChemInform Abstract: Four-Component Benzyne Coupling Reactions: A Concise Total Synthesis of Dehydroaltenuene B." ChemInform 40, no. 2 (January 13, 2009). http://dx.doi.org/10.1002/chin.200902205.

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48

BUCHWALD, S. L., A. SAYERS, B. T. WATSON, and J. C. DEWAN. "ChemInform Abstract: The Zirconocene Induced Coupling of Benzyne with Nitriles: Synthesis, Structure, and Reactions of Novel Azametallacyclopentenes." ChemInform 18, no. 51 (December 22, 1987). http://dx.doi.org/10.1002/chin.198751160.

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49

Black, Joshua Alexander, Alexander Waigum, Robert G. Adam, K. R. Shamasundar, and Andreas Köhn. "Towards an efficient implementation of internally contracted coupled-cluster methods." Journal of Chemical Physics, March 10, 2023. http://dx.doi.org/10.1063/5.0143214.

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Abstract:

A new implementation of the internally contracted multireference coupled-cluster with singles and doubles (icMRCCSD) method is presented. The new code employs an efficient tensor contraction kernel and can also avoid full four-external integral transformations, which significantly extends the scope of the applicability of icMRCCSD. The new implementation is currently restricted to the simple case of two active electrons in two orbitals and also supports the computation of spin-adapted doublet and triplet coupled-cluster wavefunctions. This contribution describes the basic approach for the automated derivation of the working equations and benchmarks the current code against efficient implementations of standard methods such as single-reference coupled-cluster singles and doubles (CCSD) and internally contracted multireference configuration interaction (icMRCI). The run times for linearized variants of icMRCCSD are only twice as long as comparable CCSD runs and similar to those of the icMRCI implementation, while the non-linear terms of more complete variants of icMRCCSD lead to an order of magnitude longer computation times. Nevertheless the new code allows for computations at larger scales than it was possible previously, with less demands on memory and disk-space resources. This is exemplified by numerical structure optimizations and harmonic force field determinations of NC2H5 isomers and the singlet and triplet state of m-benzyne. In addition, the exchange coupling of a dinuclear copper complex is determined. This work also defines a new commutator approximation for icMRCCSD which includes all terms that are also present in the single-reference CCSD method, thus yielding a consistent pair of single-reference and multireference coupled-cluster methods.

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