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Journal articles on the topic 'Cycloaddition [2+2+2]'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 May 2024

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1

Grygorenko, Oleksandr O., Viktoriia S. Moskvina, Oleksandr V. Hryshchuk, and Andriy V. Tymtsunik. "Cycloadditions of Alkenylboronic Derivatives." Synthesis 52, no. 19 (2020): 2761–80. http://dx.doi.org/10.1055/s-0040-1707159.

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The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addres

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2

Kotha, Sambasivarao, Kakali Lahiri, and Gaddamedi Sreevani. "Design and Synthesis of Aromatics through [2+2+2] Cyclotrimerization." Synlett 29, no. 18 (2018): 2342–61. http://dx.doi.org/10.1055/s-0037-1609584.

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The [2+2+2] cycloaddition reaction is a useful tool to realize unusual chemical transformations which are not achievable by traditional methods. Here, we report our work during the past two decades that involve utilization of transition-metal complexes in a [2+2+2] cyclotrimerization reaction. Several key “building blocks” were assembled by a [2+2+2] cycloaddition approach and they have been further expanded by other synthetic transformations to design unusual amino acids and peptides, diphenylalkanes, bis- and trisaryl benzene derivatives, annulated benzocycloalkanes, spirocycles, and spiroox

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3

Ahmad, Dalla Tiezza, and Orian. "In Silico Acetylene [2+2+2] Cycloadditions Catalyzed by Rh/Cr Indenyl Fragments." Catalysts 9, no. 8 (2019): 679. http://dx.doi.org/10.3390/catal9080679.

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Metal-catalyzed alkyne [2+2+2] cycloadditions provide a variety of substantial aromatic compounds of interest in the chemical and pharmaceutical industries. Herein, the mechanistic aspects of the acetylene [2+2+2] cycloaddition mediated by bimetallic half-sandwich catalysts [Cr(CO)3IndRh] (Ind = (C9H7)−, indenyl anion) are investigated. A detailed exploration of the potential energy surfaces (PESs) was carried out to identify the intermediates and transition states, using a relativistic density functional theory (DFT) approach. For comparison, monometallic parent systems, i.e., CpRh (Cp = (C5H

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4

Kanematsu, Ken, Noboru Sugimoto, Masayo Kawaoka, Sinkoo Yeo, and Motoo Shiro. "Competitive intramolecular [4+2] cycloaddition and [2+2] cycloaddition of sulfonylallene." Tetrahedron Letters 32, no. 10 (1991): 1351–54. http://dx.doi.org/10.1016/s0040-4039(00)79665-1.

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5

Tanaka, K., K. Masutomi, N. Sakiyama, and K. Noguchi. "Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition." Synfacts 9, no. 05 (2013): 0575. http://dx.doi.org/10.1055/s-0033-1338458.

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6

Rovis, T., and D. Dalton. "Rhodium-Catalyzed Enantioselective [2+2+2] Cycloaddition." Synfacts 9, no. 09 (2013): 1030. http://dx.doi.org/10.1055/s-0033-1339688.

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7

Meyer, Vera J., Christoph Ascheberg, and Meike Niggemann. "Calcium-Catalyzed Formal [2+2+2] Cycloaddition." Chemistry - A European Journal 21, no. 17 (2015): 6371–74. http://dx.doi.org/10.1002/chem.201500181.

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8

Fleming, Steven A., and Susan C. Ward. "Stereocontrolled photochemical [2 + 2] cycloaddition." Tetrahedron Letters 33, no. 8 (1992): 1013–16. http://dx.doi.org/10.1016/s0040-4039(00)91847-1.

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9

Treutwein, Jonas, and Gerhard Hilt. "Cobalt-Catalyzed [2+2] Cycloaddition." Angewandte Chemie International Edition 47, no. 36 (2008): 6811–13. http://dx.doi.org/10.1002/anie.200801778.

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10

Treutwein, Jonas, and Gerhard Hilt. "Cobalt-katalysierte [2+2]-Cycloaddition." Angewandte Chemie 120, no. 36 (2008): 6916–19. http://dx.doi.org/10.1002/ange.200801778.

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11

Feltenberger, John B., Ryuji Hayashi, Yu Tang, Eric S. C. Babiash, and Richard P. Hsung. "Enamide-Benzyne-[2 + 2] Cycloaddition: Stereoselective Tandem [2 + 2]−Pericyclic Ring-Opening−IntramolecularN-Tethered [4 + 2] Cycloadditions." Organic Letters 11, no. 16 (2009): 3666–69. http://dx.doi.org/10.1021/ol901434g.

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12

Peng, Shiyong, Danqing Ji, and Jiangtao Sun. "Gold-catalyzed [2+2+2+2]-annulation of 1,3,5-hexahydro-1,3,5-triazines with alkoxyallenes." Chemical Communications 53, no. 95 (2017): 12770–73. http://dx.doi.org/10.1039/c7cc07554e.

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13

Čížková, Martina, Viliam Kolivoška, Ivana Císařová, David Šaman, Lubomír Pospíšil, and Filip Teplý. "Nitrogen heteroaromatic cations by [2+2+2] cycloaddition." Org. Biomol. Chem. 9, no. 2 (2011): 450–62. http://dx.doi.org/10.1039/c0ob00507j.

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14

Taylor, Mark S., and Timothy M. Swager. "Triptycenediols by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition." Organic Letters 9, no. 18 (2007): 3695–97. http://dx.doi.org/10.1021/ol701642j.

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15

Domínguez, Gema, and Javier Pérez-Castells. "Recent advances in [2+2+2] cycloaddition reactions." Chemical Society Reviews 40, no. 7 (2011): 3430. http://dx.doi.org/10.1039/c1cs15029d.

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16

Shibata, Takanori, and Kyoji Tsuchikama. "Recent advances in enantioselective [2 + 2 + 2] cycloaddition." Organic & Biomolecular Chemistry 6, no. 8 (2008): 1317. http://dx.doi.org/10.1039/b720031e.

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17

Pla-Quintana, Anna, and Anna Roglans. "Chiral Induction in [2+2+2] Cycloaddition Reactions." Asian Journal of Organic Chemistry 7, no. 9 (2018): 1706–18. http://dx.doi.org/10.1002/ajoc.201800291.

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18

KANEMATSU, K., N. SUGIMOTO, M. KAWAOKA, S. YEO, and M. SHIRO. "ChemInform Abstract: Competitive Intramolecular (4 + 2)Cycloaddition and (2 + 2) Cycloaddition of Sulfonylallene." ChemInform 23, no. 2 (2010): no. http://dx.doi.org/10.1002/chin.199202197.

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19

Hayashi, Yujiro, and Koichi Narasaka. "ChemInform Abstract: [2 + 2] Cycloaddition Reactions." ChemInform 31, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.200018221.

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20

Braunschweig, Holger, Michael Burzler, Krzysztof Radacki, and Fabian Seeler. "Borylene Metathesis through [2+2] Cycloaddition." Angewandte Chemie International Edition 46, no. 42 (2007): 8071–73. http://dx.doi.org/10.1002/anie.200702982.

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21

Winne, Johan, Jan Hullaert, Bram Denoo, Mien Christiaens, and Brenda Callebaut. "Heterocycles as Moderators of Allyl Cation Cycloaddition Reactivity." Synlett 28, no. 18 (2017): 2345–52. http://dx.doi.org/10.1055/s-0036-1588511.

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For the rapid elaboration of polycarbocyclic scaffolds, prevalent in many important families of terpenoid natural products, allyl cations derived from simple heterocyclic alcohols can be used as versatile reaction partners in both (4+3) and (3+2) cycloaddition pathways. Our recent progress in this area is outlined, pointing towards the untapped potential of heterocycles to act as reagents in novel or known but challenging organic transformations.1 Heterocyclic Reagents2 Cycloadditions and Allyl Cations3 Furfuryl Cations in Cycloadditions4 Heterocycle-Substituted Cations in Cycloadditions5 Mech

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22

Petko, Dina, Austin Pounder, and William Tam. "Ruthenium-Catalyzed [2+2+2] Bis-Homo-Diels–Alder Cycloadditions of 1,5-Cyclooctadiene with Alkynyl Phosphonates." Synthesis 51, no. 22 (2019): 4271–78. http://dx.doi.org/10.1055/s-0039-1690612.

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The ruthenium-catalyzed [2+2+2] bis-homo-Diels–Alder cycloaddition between 1,5-cyclooctadiene and alkynyl phosphonates was investigated. Various alkynyl phosphonate moieties were found to be compatible with the cycloaddition to give the tricyclo[4.2.2.02,5]dec-7-ene tricyclic compounds in yields of 46–97%.

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23

Liu, Ruzhang, Rong-Guo Shi, Jing Sun, and Chao-Guo Yan. "A [3 + 2]–[4 + 2]–[3 + 2] cycloaddition sequence of isoquinolinium ylide." Organic Chemistry Frontiers 4, no. 3 (2017): 354–57. http://dx.doi.org/10.1039/c6qo00615a.

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24

Calleja, Pilar, Michael Muratore, Tania Jiménez, and Antonio Echavarren. "Diastereoselective Gold(I)-Catalyzed [2+2+2] Cycloaddition of Oxo-1,5-enynes." Synthesis 48, no. 19 (2016): 3183–98. http://dx.doi.org/10.1055/s-0035-1562452.

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The intramolecular gold(I)-catalyzed [2+2+2] cycloaddition of oxo-1,5-enynes bearing protected homopropargylic alcohols provides access to oxatricyclic adducts with good to excellent diastereoselectivity.

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25

Tateishi, Keiichiro, Keiichi Noguchi, and Akio Saito. "2-Picoline catalyst-triggered [2 + 2 + 2] cycloaddition-type reaction of acetylenedicarboxylates, aldehydes and alkenes." Organic & Biomolecular Chemistry 16, no. 33 (2018): 5965–68. http://dx.doi.org/10.1039/c8ob01774c.

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2-Picoline efficiently catalyzes the formation of α,β-enones from acetylenedicarboxylates and aldehydes in the presence of alkenes, thereby leading to pyrans with complete regioselectivities. This method is represented as a first example of catalytic and metal-free [2 + 2 + 2] cycloaddition of three different components.

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26

Shibata, T., T. Uchiyama, and K. Endo. "Rhodium-Catalyzed [2+2+2] Cycloaddition of Branched Triynes." Synfacts 2009, no. 12 (2009): 1364. http://dx.doi.org/10.1055/s-0029-1218318.

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27

Yamamoto, Y., K. Hattori, and H. Nishiyama. "Synthesis of p-Diiodobenzenes by [2+2+2] Cycloaddition." Synfacts 2006, no. 9 (2006): 0899. http://dx.doi.org/10.1055/s-2006-942033.

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28

Rovis, T., and R. Yu. "Indolizinone and Quinolizinone via Asymmetric [2+2+2] Cycloaddition." Synfacts 2006, no. 12 (2006): 1209. http://dx.doi.org/10.1055/s-2006-955576.

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29

Meyer, Vera J., Christoph Ascheberg, and Meike Niggemann. "ChemInform Abstract: Calcium-Catalyzed Formal [2 + 2 + 2] Cycloaddition." ChemInform 46, no. 36 (2015): no. http://dx.doi.org/10.1002/chin.201536173.

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30

Lledó, A., A. Pla-Quintana, and A. Roglans. "Allenes, versatile unsaturated motifs in transition-metal-catalysed [2+2+2] cycloaddition reactions." Chemical Society Reviews 45, no. 8 (2016): 2010–23. http://dx.doi.org/10.1039/c5cs00535c.

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31

Laghrib, Naoual, Mohamed Azrour, Jean-Claude Daran, Rachid Fihi, and Lhou Majidi. "(3SR,2′SR)-3-(2′-Anilino-2′-phenylethyl)phthalide." Acta Crystallographica Section E Structure Reports Online 63, no. 11 (2007): o4333. http://dx.doi.org/10.1107/s1600536807050039.

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Evolution of the major spiroadduct obtained by cycloaddition of C,N-diphenylnitrone with 3-methylenephthalide in Zn/3 M HCl media gives a rearrangement product. The reaction did not stop at the formation of an aminoalcohol but was followed by dehydration; the title compound, C22H19NO2, was obtained after hydrogenation. It exists in the diastereoisomer SS/RR form. The packing is stabilized by weak N—H...O and C—H...O hydrogen-bond interactions.

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32

Padwa, Albert, G. Davon Kennedy, and M. Woods Wannamaker. "Cycloaddition reactions of strained ring systems. Photosensitized [2 + 2] cycloadditions of 2-(acyloxy)-substituted cyclopropenes." Journal of Organic Chemistry 50, no. 25 (1985): 5334–41. http://dx.doi.org/10.1021/jo00225a064.

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33

Minakawa, Maki, Tomoki Ishikawa, Junya Namioka, Souichirou Hirooka, Biao Zhou, and Motoi Kawatsura. "Iron-catalyzed [2 + 2 + 2] cycloaddition of trifluoromethyl group substituted unsymmetrical internal alkynes." RSC Adv. 4, no. 78 (2014): 41353–56. http://dx.doi.org/10.1039/c4ra06973k.

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Iron-catalyzed [2 + 2 + 2] intermolecular cycloaddition of trifluoromethyl group substituted unsymmetrical internal alkynes afforded the corresponding trifluoromethyl group substituted benzene derivatives in high yield with excellent selectivity.

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34

Firooznia, Fariborz, Robert F. Kester, and Steven J. Berthel. "ChemInform Abstract: [2 + 2], [3 + 2] and [2 + 2 + 2] Cycloaddition Reactions of Indole Derivatives." ChemInform 42, no. 43 (2011): no. http://dx.doi.org/10.1002/chin.201143233.

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35

Obenhuber, A. H., T. L. Gianetti, R. G. Bergman, and J. Arnold. "Regioselective [2+2] and [4+2] cycloaddition reactivity in an asymmetric niobium(bisimido) moiety towards unsaturated organic molecules." Chemical Communications 51, no. 7 (2015): 1278–81. http://dx.doi.org/10.1039/c4cc07851a.

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The asymmetric bis-imido structure and the lability of the diethyl ether linkage in complex 1 provide a niobium complex that undergoes regioselective [4+2] cycloaddition reactions with an α,β-unsaturated ketone and cycloaddition reactions that involve bond formation to the MAD ligand (MAD = monoazabutadiene).

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36

Brummond, Kay M., Honghe Wan, and Joseph L. Kent. "An Intramolecular Allenic [2 + 2 + 1] Cycloaddition." Journal of Organic Chemistry 63, no. 19 (1998): 6535–45. http://dx.doi.org/10.1021/jo980548c.

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37

Sarkar, Debayan, Nabakumar Bera, and Subrata Ghosh. "[2+2] Photochemical Cycloaddition in Organic Synthesis." European Journal of Organic Chemistry 2020, no. 10 (2019): 1310–26. http://dx.doi.org/10.1002/ejoc.201901143.

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38

FLEMING, S. A., and S. C. WARD. "ChemInform Abstract: Stereocontrolled Photochemical (2 + 2)Cycloaddition." ChemInform 23, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199237131.

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39

Braunschweig, Holger, Michael Burzler, Krzysztof Radacki, and Fabian Seeler. "Borylen-Metathese über eine [2+2]-Cycloaddition." Angewandte Chemie 119, no. 42 (2007): 8217–19. http://dx.doi.org/10.1002/ange.200702982.

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40

Pla-Quintana, Anna, and Anna Roglans. "The Choice of Rhodium Catalysts in [2+2+2] Cycloaddition Reaction: A Personal Account." Molecules 27, no. 4 (2022): 1332. http://dx.doi.org/10.3390/molecules27041332.

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[2+2+2] Cycloaddition reaction is a captivating process that assembles six-membered rings from three unsaturations with complete atom economy. Of the multiple transition metals that can be used to catalyze this reaction, rhodium offers many advantages. These include high activity and versatility, but especially the ability to easily tune the reactivity and selectivity by the modification of the ligands around the metal. In this personal account, we summarize our endeavours in the development of efficient and sustainable [2+2+2] cycloaddition reactions to prepare products of interest, develop c

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41

Chowdhury, Hrishikesh, and Avijit Goswami. "Synthesis of 3-(2-thiopyridyl)indoles via the ruthenium catalyzed [2 + 2 + 2] cycloaddition of diynes and 3-thiocyanatoindoles." Organic & Biomolecular Chemistry 15, no. 27 (2017): 5824–30. http://dx.doi.org/10.1039/c7ob01101f.

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A highly efficient protocol for the synthesis of 3-(2-thiopyridyl)indoles via the ruthenium(ii) catalyzed [2 + 2 + 2] cycloaddition reaction of α,ω-diynes with 3-thiocyanatoindoles under mild reaction conditions has been developed.

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42

Liu, Mingyu, Mark S. Taylor, and Timothy M. Swager. "Correction to Triptycenediols by Rhodium-Catalyzed [2 + 2 + 2] Cycloaddition." Organic Letters 23, no. 16 (2021): 6599. http://dx.doi.org/10.1021/acs.orglett.1c02508.

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43

Kotha, Sambasivarao, Kumar Mohanraja, and Susheel Durani. "Constrained phenylalanyl peptides via a [2+2+2]-cycloaddition strategy." Chemical Communications, no. 19 (2000): 1909–10. http://dx.doi.org/10.1039/b005605g.

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44

Gandon, Vincent, Corinne Aubert, and Max Malacria. "Recent progress in cobalt-mediated [2 + 2 + 2] cycloaddition reactions." Chemical Communications, no. 21 (2006): 2209. http://dx.doi.org/10.1039/b517696b.

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45

Shibata, T., Y. Arai, and Y.-K. Tahara. "Enantioselective [2+2+2] Cycloaddition of 1,6-Enynes and Alkynes." Synfacts 2006, no. 01 (2005): 0048. http://dx.doi.org/10.1055/s-2005-921680.

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46

Louie, Janis, John E. Gibby, Marc V. Farnworth, and Thomas N. Tekavec. "Efficient Nickel-Catalyzed [2 + 2 + 2] Cycloaddition of CO2and Diynes." Journal of the American Chemical Society 124, no. 51 (2002): 15188–89. http://dx.doi.org/10.1021/ja027438e.

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47

Tran-Van, Anne-Florence, Elena Huxol, Jonathan M. Basler, et al. "Synthesis of Substituted [8]Cycloparaphenylenes by [2 + 2 + 2] Cycloaddition." Organic Letters 16, no. 6 (2014): 1594–97. http://dx.doi.org/10.1021/ol500194s.

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48

Reinecke, Manfred G., E. Sherwood Brown, Bruce P. Capehart, David E. Minter, and Richard K. Freeman. "3,4-Didehydropyridine plus cyclopentadiene: [2+2] or [4+2]-cycloaddition ?" Tetrahedron 44, no. 18 (1988): 5675–80. http://dx.doi.org/10.1016/s0040-4020(01)81429-0.

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49

Deiters, A., R. Senaiar, and D. Young. "Polymer-Supported Synthesis of Pyridines via [2+2+2] Cycloaddition." Synfacts 2006, no. 6 (2006): 0627. http://dx.doi.org/10.1055/s-2006-941797.

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50

Siegel, J., Y. T. Wu, T. Hayama, K. Baldridge, and A. Linden. "Synthesis of Indeno-Fused Aromatics by [2+2+2] Cycloaddition." Synfacts 2006, no. 8 (2006): 0783. http://dx.doi.org/10.1055/s-2006-941962.

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