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Journal articles on the topic 'Copper-catalyzed 3+2 cycloaddition'

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Published: 24 April 2022

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1

Cheng, C. H., H. T. Chang, and T. Jayanth. "Copper-Catalyzed Diastereoselective [3+2] Cycloaddition." Synfacts 2007, no. 7 (July 2007): 0720. http://dx.doi.org/10.1055/s-2007-968623.

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2

Siva Prasanna Sanka, R. V., Balaji K., Yves Leterrier, Shyam Pandey, Monika Srivastava, Anurag Srivastava, Wolfgang H. Binder, Sravendra Rana, and Véronique Michaud. "Nitrogen-doped graphene stabilized copper nanoparticles for Huisgen [3+2] cycloaddition “click” chemistry." Chemical Communications 55, no. 44 (2019): 6249–52. http://dx.doi.org/10.1039/c9cc02057h.

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3

Schienebeck, Casi M., Xiaoxun Li, Xing-zhong Shu, and Weiping Tang. "3-Acyloxy-1,4-enyne: A new five-carbon synthon for rhodium-catalyzed [5 + 2] cycloadditions." Pure and Applied Chemistry 86, no. 3 (March 20, 2014): 409–17. http://dx.doi.org/10.1515/pac-2014-5042.

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Abstract Seven-membered rings are ubiquitous in natural products and pharmaceutical agents, and their syntheses continue to stimulate the development of novel synthetic methods. The [5 + 2] cycloaddition is one of the most efficient ways to access seven-membered rings since the two-carbon components (alkenes, alkynes, or allenes) are readily available. Prior to our study, however, there was only one type of transition-metal-catalyzed [5 + 2] cycloaddition: the reaction between vinylcyclopropanes and alkenes, alkynes, or allenes. We recently developed a new type of transition-metal-catalyzed [5 + 2] cycloaddition, where the five-carbon building block is 3-acyloxy-1,4-enyne (ACE). Our recent progress on Rh-catalyzed intra- and intermolecular [5 + 2] cycloadditions of ACEs and alkynes is summarized in this article. Using chiral propargylic esters, bicyclic products were prepared in high optical purity by the intramolecular [5 + 2] cycloadditions. Monocyclic seven-membered rings were synthesized by intermolecular [5 + 2] cycloaddition of ACEs and alkynes. Kinetic studies indicated that the rate of this intermolecular cycloaddition was significantly accelerated when the acetate was replaced by dimethylaminobenzoate. DFT calculations suggested that novel metallacycles were generated by a Rh-promoted oxidative cycloaddition of 1,4-enynes accompanied by a 1,2-acyloxy migration of propargylic esters.
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4

Xie, Ying, Yulong Li, Xun Chen, Yingle Liu, and Wei Zhang. "Copper/amine-catalyzed formal regioselective [3 + 2] cycloaddition of an α,β-unsaturated O-acetyl oxime with enals." Organic Chemistry Frontiers 5, no. 10 (2018): 1698–701. http://dx.doi.org/10.1039/c8qo00204e.

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5

Xie, Zhiyu, Fei Li, Liangfeng Niu, Hongbing Li, Jincai Zheng, Ruijing Han, Zhiyu Ju, Shanshan Li, and Dandan Li. "CuBr/NHPI co-catalyzed aerobic oxidative [3 + 2] cycloaddition-aromatization to access 5,6-dihydro-pyrrolo[2,1-a]isoquinolines." Organic & Biomolecular Chemistry 18, no. 35 (2020): 6889–98. http://dx.doi.org/10.1039/d0ob01403f.

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6

Wang, Qian, Timothy R. Chan, Robert Hilgraf, Valery V. Fokin, K. Barry Sharpless, and M. G. Finn. "Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition." Journal of the American Chemical Society 125, no. 11 (March 2003): 3192–93. http://dx.doi.org/10.1021/ja021381e.

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7

Yuan, Yang, Zhan-Jiang Zheng, Fei Ye, Jun-Han Ma, Zheng Xu, Xing-Feng Bai, Li Li, and Li-Wen Xu. "Highly efficient desymmetrization of cyclopropenes to azabicyclo[3.1.0]hexanes with five continuous stereogenic centers by copper-catalyzed [3 + 2] cycloadditions." Organic Chemistry Frontiers 5, no. 18 (2018): 2759–64. http://dx.doi.org/10.1039/c8qo00761f.

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An unprecedented copper-catalyzed desymmetrization/cycloaddition reaction of 1,1-disubstituted cyclopropenes provides an efficient access to azabicyclo[3.1.0]hexanes bearing five continuous carbon-stereogenic centers.
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8

Xu, Bing, Zhan-Ming Zhang, Bing Liu, Shan Xu, Lu-Jia Zhou, and Junliang Zhang. "Copper(i)-catalyzed asymmetric exo-selective [3+2] cycloaddition of azomethine ylides with β-trifluoromethyl β,β-disubstituted enones." Chemical Communications 53, no. 58 (2017): 8152–55. http://dx.doi.org/10.1039/c7cc03015k.

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A copper-catalyzed asymmetricexo-selective dipolar cycloaddition of β-trifluoromethyl β,β-disubstituted enones with azomethine ylides was developed, which provides an efficient access to valuable pyrrolidines bearing a trifluoromethylated all-carbon quaternary stereocenter.
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9

Link, A. James, and David A. Tirrell. "Cell Surface Labeling ofEscherichia colivia Copper(I)-Catalyzed [3+2] Cycloaddition." Journal of the American Chemical Society 125, no. 37 (September 2003): 11164–65. http://dx.doi.org/10.1021/ja036765z.

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10

Román-Maldonado, Eloisa, Horacio Reyes, Miguel A. Sanchez-Carmona, Nelly González-Rivas, and Erick Cuevas-Yañez. "1-(2-Chlorobenzyloxy)-3-[1,2,3]triazol-1-yl-propan-2-ol Derivatives: Synthesis, Characterization, and DFT-Based Descriptors Analysis." Journal of Chemistry 2017 (2017): 1–9. http://dx.doi.org/10.1155/2017/4783608.

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A novel series of 1-(2-chlorobenzyloxy)-3-[1,2,3]triazol-1-yl-propan-2-ol derivatives was designed and synthesized using copper catalyzed alkyne-azide cycloaddition in the key step. Theoretical investigation of molecular and electronic properties by means of global and local reactivity indexes of the synthetized compounds was carried out, using DFT (Density Functional Theory) at PBEPBE/6-31++G⁎⁎level.
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11

Liang, Hao, Xiaobo He, Yaqi Zhang, Bin Chen, Jia-sheng Ouyang, Yongsu Li, Bendu Pan, Chitreddy V. Subba Reddy, Wesley Ting Kwok Chan, and Liqin Qiu. "Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes." Chemical Communications 56, no. 77 (2020): 11429–32. http://dx.doi.org/10.1039/d0cc04373g.

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The copper(ii)-catalyzed (4+1) cyclizations and copper(i)-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes have been successfully developed. The corresponding highly functionalized heterocyclic products were prepared conveniently.
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12

Li, Qing, Chuan-Jin Hou, Yun-Ze Hui, Yan-Jun Liu, Rui-Feng Yang, and Xiang-Ping Hu. "Tridentate P,N,N-ligand promoted copper-catalyzed [3 + 2] cycloaddition of propargylic esters with β-enamino esters: synthesis of highly functionalized pyrroles." RSC Advances 5, no. 104 (2015): 85879–83. http://dx.doi.org/10.1039/c5ra19304d.

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By employment of a newly developed tridentate P,N,N-ligand, a copper-catalyzed [3 + 2] cycloaddition of propargylic esters with β-enamino esters for the construction of highly functionalized pyrroles has been developed.
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13

Yan, Kelu, Daoshan Yang, Wei Wei, Pengfei Sun, Yunxiang Lu, and Hua Wang. "A copper-catalyzed cascade reaction of o-bromoarylisothiocyanates with isocyanides leading to benzo[d]imidazo[5,1-b]thiazoles under ligand-free conditions." Organic Chemistry Frontiers 3, no. 5 (2016): 556–60. http://dx.doi.org/10.1039/c6qo00030d.

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14

Li, Yujin, Zihua Yu, Xue Tang, Chenxi Huang, Yehan Shang, Qing Ye, and Liang Han. "Copper(I) Iodide Promoted [3+2]-Cycloaddition/Oxidation to Construct Pyrrolo[2,1-a]isoquinolinoquinones from Naphthoquinones and Tetrahydroisoquinolines." Synlett 33, no. 06 (January 3, 2022): 563–68. http://dx.doi.org/10.1055/a-1729-6586.

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AbstractA copper-catalyzed, three-component, one-pot, 1,3-dipole cycloaddition/oxidation has been developed to construct pyrrolo[2,1-a]isoquinolinoquinone derivatives, with environmentally friendly oxygen as the oxidant. The pyrrolo[2,1-a]isoquinolinoquinone products were obtained from naturally available tetrahydroisoquinolines, 1,4-naphthoquinones, and benzaldehydes in medium yields.
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15

Li, Yi-Jin, Xue Li, Shao-Xiao Zhang, Yu-Long Zhao, and Qun Liu. "Copper(ii)-catalyzed oxidative [3+2] cycloaddition reactions of secondary amines with α-diazo compounds: a facile and efficient synthesis of 1,2,3-triazoles." Chemical Communications 51, no. 58 (2015): 11564–67. http://dx.doi.org/10.1039/c5cc02092a.

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A novel copper-catalyzed [3+2] cycloaddition reaction of secondary amines with α-diazo compounds has been developed via a cross-dehydrogenative coupling process under very mild conditions with molecular oxygen as a co-oxidant.
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16

Shaygan Nia, Ali, Sravendra Rana, Diana Döhler, Xavier Noirfalise, Alice Belfiore, and Wolfgang H. Binder. "Click chemistry promoted by graphene supported copper nanomaterials." Chem. Commun. 50, no. 97 (2014): 15374–77. http://dx.doi.org/10.1039/c4cc07774a.

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Highly dispersed copper nanoparticles immobilized graphene nanosheets were prepared and used as a recyclable and reusable heterogeneous catalyst with excellent catalytic activity to achieve Cu(i)-catalyzed [3+2] cycloaddition “click” chemistry under both solvent and bulk conditions.
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17

Deng, Yongming, Qing-Qing Cheng, and Michael Doyle. "Asymmetric [3+3] Cycloaddition for Heterocycle Synthesis." Synlett 28, no. 14 (July 5, 2017): 1695–706. http://dx.doi.org/10.1055/s-0036-1588453.

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Asymmetric syntheses of six-membered ring heterocycles are important research targets not only in synthetic organic chemistry but also in pharmaceuticals. The [3+3]-cycloaddition methodology is a complementary strategy to [4+2] cycloaddition for the synthesis of heterocyclic compounds. Recent progress in [3+3]-cycloaddition processes provide powerful asymmetric methodologies for the construction of six-membered ring heterocycles with one to three heteroatoms in the ring. In this account, synthetic efforts during the past five years toward the synthesis of enantioenriched six-membered ring heterocycles through asymmetric [3+3] cycloaddition are reported. Asymmetric organocatalysis uses chiral amines, thioureas, phosphoric acids, or NHC catalysis to achieve high enantiocontrol. Transition-metal catalysts used as chiral Lewis acids to activate a dipolar species is an alternative approach. The most recent advance, chiral transition-metal-catalyzed reactions of enoldiazo compounds, has contributed toward the versatile and highly selective synthesis of six-membered heterocyclic compounds.1 Introduction2 Asymmetric Formal [3+3]-Cycloaddition Reactions by Organo­catalysis2.1 By Amino-Catalysis2.2 By N-Heterocyclic Carbenes2.3 By Bifunctional Tertiary Amine-thioureas2.4 By Chiral Phosphoric Acids3 Asymmetric Formal [3+3]-Cycloaddition Reactions by Transition-Metal Catalysis3.1 Copper Catalysis3.2 Other Transition-Metal Catalysis4 Asymmetric [3+3]-Cycloaddition Reactions of Enoldiazo Compounds4.1 Asymmetric [3+3]-Cycloaddition Reactions of Nitrones with Electrophilic Metallo-enolcarbene Intermediates4.2 Dearomatization in Asymmetric [3+3]-Cycloaddition Reactions of Enoldiazoacetates4.3 Asymmetric Stepwise [3+3]-Cycloaddition Reaction of Enoldiazoacetates with Hydrazones5 Summary and Outlook
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18

Liu, Zhen-Ting, and Xiang-Ping Hu. "Copper-catalyzed, silver-mediated formal [3+2] cycloaddition of simple alkynes with β-ketoesters through propargylic C(sp3)–H functionalization." Chemical Communications 54, no. 100 (2018): 14100–14103. http://dx.doi.org/10.1039/c8cc08013e.

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The propargylic C(sp3)–H functionalization strategy has been successfully employed in the copper-catalyzed [3+2] cycloaddition of simple alkynes with β-ketoesters. Under optimal conditions, the reaction proceeds smoothly to give a variety of highly functionalized furans in moderate to high yields.
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19

Yamada, Mizuki, Mio Matsumura, Yuki Uchida, Masatoshi Kawahata, Yuki Murata, Naoki Kakusawa, Kentaro Yamaguchi, and Shuji Yasuike. "Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides." Beilstein Journal of Organic Chemistry 12 (June 23, 2016): 1309–13. http://dx.doi.org/10.3762/bjoc.12.123.

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Trisubstituted 5-stibano-1H-1,2,3-triazoles were synthesized in moderate to excellent yields by the Cu-catalyzed [3 + 2] cycloaddition of a ethynylstibane with organic azides in the presence of CuBr (5 mol %) under aerobic conditions. The reaction of 5-stibanotriazole with HCl, I2, and NOBF4 afforded 1-benzyl-4-phenyltriazole, 1-benzyl-5-iodo-4-phenyltriazole, and a pentavalent organoantimony compound, respectively.
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20

Cui, Hao, Ke Li, Yue Wang, Manman Song, Congcong Wang, Donghui Wei, Er-Qing Li, Zheng Duan, and François Mathey. "Copper(i)/Ganphos catalysis: enantioselective synthesis of diverse spirooxindoles using iminoesters and alkyl substituted methyleneindolinones." Organic & Biomolecular Chemistry 18, no. 19 (2020): 3740–46. http://dx.doi.org/10.1039/d0ob00546k.

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A copper/Ganphos-catalyzed asymmetric 1,3-dipolar cycloaddition of glycine iminoesters with alkyl substituted 3-methylene-2-oxindoles is described, producing the spiro[pyrrolidin-3,3′-oxindole]s in good yields with high ee.
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21

Vanhaecht, S., T. Quanten, and T. N. Parac-Vogt. "A mild post-functionalization method for the vanadium substituted P2W15V3 Wells–Dawson polyoxometalate based on a copper catalyzed azide–alkyne cycloaddition." Dalton Transactions 46, no. 31 (2017): 10215–19. http://dx.doi.org/10.1039/c7dt02450a.

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A novel post-functionalization method for the vanadium substituted P2W15V3 Wells–Dawson polyoxometalate has been developed using a copper catalyzed azide–alkyne cycloaddition.
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22

Hanson, Sarah R, William A Greenberg, and Chi-Huey Wong. "Probing Glycans With the Copper(I)-Catalyzed [3+2] Azide-Alkyne Cycloaddition." QSAR & Combinatorial Science 26, no. 11-12 (November 14, 2007): 1243–52. http://dx.doi.org/10.1002/qsar.200740112.

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23

Depa, Navaneetha, and Harikrishna Erothu. "DESIGN AND SYNTHESIS OF NOVEL PERILLYL-4HPYRANTRIAZOLE DERIVATIVES." Rasayan Journal of Chemistry 15, no. 01 (2022): 302–9. http://dx.doi.org/10.31788/rjc.2022.1516629.

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We report a set of twelve rationally designed and library of perillyl-4H-pyrantriazole derivatives (6a-6l) through a sequence of a multicomponent reaction followed by copper-catalyzed cycloaddition. The intermediate 4-aryl-4Hpyran (4) was obtained by three-component condensation of 5,5-dimethylcyclohexane-1,3-dione) (1), 4-(prop-2-yn1-yloxy) benzaldehyde (2) and malononitrile (3). To this intermediate, azido benzenes (5) were subjected using copper catalyze cycloaddition to produce perillyl-4H-pyrantriazole derivatives in better to good yields. All compounds were validated by mass, 13C-NMR, FTIR and 1H-NMR spectrometry.
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24

Trost, B., J. Stambuli, S. Silverman, and U. Schwörer. "Asymmetric Palladium-Catalyzed [3+2] Cycloaddition." Synfacts 2007, no. 1 (January 2007): 0066. http://dx.doi.org/10.1055/s-2006-955717.

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25

Zhou, Yuxuan, Fanghui Ma, Ping Lu, and Yanguang Wang. "Preparation of spiro[imidazolidine-4,3′-indolin]-2′-imines via copper(i)-catalyzed formal [2 + 2 + 1] cycloaddition of 3-diazoindolin-2-imines and triazines." Organic & Biomolecular Chemistry 17, no. 39 (2019): 8849–52. http://dx.doi.org/10.1039/c9ob01767d.

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26

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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27

Yavari, Issa, and Omid Khaledian. "Copper-Catalyzed Tandem Dehydrocyanation and [3+2] Cyclo­addition Reactions of Phenacylmalononitriles: Regioselective Synthesis of Functionalized 4-Benzoyl-5-cyanopyrazoles under Mild Conditions." Synthesis 52, no. 09 (February 6, 2020): 1379–86. http://dx.doi.org/10.1055/s-0039-1691591.

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A novel copper-catalyzed [3+2] cycloaddition reaction with concomitant in situ generation of benzoylacrylonitriles and nitrile imines from phenacylmalononitriles and hydrazonoyl chlorides, respectively, is reported. The reaction was performed using copper(I) chloride as catalyst and N-methylimidazole as a clean complexing agent/weak base to afford the functionalized 4-benzoyl-5-cyanopyrazoles in moderate to good yields and excellent regioselectivity under ambient conditions. This method provides rapid access to a wide range of highly functionalized 4-benzoyl-5-cyanopyrazoles.
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28

Kuila, Bilash, Maninderjeet Kaur, Prabhpreet Singh, and Gaurav Bhargava. "Transition-Metal-Catalyzed [3+2+2] Cycloaddition Reactions." European Journal of Organic Chemistry 2018, no. 7 (December 21, 2017): 853–68. http://dx.doi.org/10.1002/ejoc.201701116.

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29

Szafrański, Przemysław W., Patryk Kasza, Mariusz Kępczyński, and Marek T. Cegła. "Fluorescent 1,2,3-triazole derivative of 3′-deoxy-3-azidothymidine: synthesis and absorption/emission spectra." Heterocyclic Communications 21, no. 5 (October 1, 2015): 263–67. http://dx.doi.org/10.1515/hc-2015-0195.

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Abstract3′-Deoxy-3-azidothymidine (AZT, zidovudine) is a nucleoside-analog reverse transcriptase inhibitor, successfully used against the human immunodeficiency virus (HIV). Its structure contains an azide function, which makes it a useful substrate for 1,2,3-triazole synthesis, using the copper-catalyzed azide-alkyne cycloaddition, the flagship reaction of ‘click chemistry’. Herein we present the synthesis and spectral characterization of its 1,2,3-triazole derivative containing a fluorenylmethyloxycarbonyl (fmoc) fluorescent fragment. The preparation and characteristics of a novel fluorescent probe, 9H-fluoren-9-ylmethyl prop-2-yn-1-yl carbonate (propargyl-fmoc) is also presented.
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30

Ding, Wen-Ping, Juan Du, Xiu-Yan Liu, Di Chen, Chang-Hua Ding, Qing-Hai Deng, and Xue-Long Hou. "Palladium-Catalyzed [3+2] Cycloaddition of Vinylcyclopropane and Ketones." Synlett 30, no. 08 (April 10, 2019): 947–50. http://dx.doi.org/10.1055/s-0037-1611477.

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31

He, Xinwei, Ruxue Li, Mengqing Xie, Jiahui Duan, Qiang Tang, and Yongjia Shang. "Copper-catalyzed cascade three-component azide–alkyne cycloaddition/condensation/transesterification: easy access to 3-triazolylcoumarins." New Journal of Chemistry 44, no. 28 (2020): 12266–73. http://dx.doi.org/10.1039/d0nj02100h.

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A novel and efficient strategy has been developed for the synthesis of 3-triazolylcoumarins in a one-pot, copper-catalyzed multicomponent reaction involving a cascade reaction of salicylaldehydes, ethyl 2-azidoacetate, and arylacetylenes.
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Ma, Xiao-Pan, Cai-Mei Nong, Yu-Feng Liang, Pei-Pei Xu, Xiu-Yun Guo, Cui Liang, Cheng-Xue Pan, Gui-Fa Su, and Dong-Liang Mo. "An Yb(OTf)3 and visible light relay catalyzed [3 + 2] cycloaddition/[3,3]-rearrangement/[4 + 2] cycloaddition in one pot to prepare oxazonine-fused endoperoxides." Green Chemistry 22, no. 12 (2020): 3827–34. http://dx.doi.org/10.1039/d0gc00929f.

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A Yb(OTf)3 and visible light relay catalyzed [3 + 2] cycloaddition/[3,3]-rearrangement/[4 + 2] cycloaddition in one pot was developed to prepare oxazonine-fused endoperoxides in good yields from N-vinyl nitrones and methylenecyclopropanes.
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33

Petek, Nejc, Uroš Grošelj, Jurij Svete, Franc Požgan, Drago Kočar, and Bogdan Štefane. "Eosin Y-Catalyzed Visible-Light-Mediated Aerobic Transformation of Pyrazolidine-3-One Derivatives." Catalysts 10, no. 9 (September 1, 2020): 981. http://dx.doi.org/10.3390/catal10090981.

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By utilizing an underexplored reactivity of N1-substituted pyrazolidine-3-ones, we developed a visible-light-induced aerobic oxidation of N1-substituted pyrazolidine-3-one derivatives yielding the corresponding azomethine imines. The resulting azomethine imines can be further reacted with ynones in situ under copper catalyzed [3 + 2] cycloaddition reaction conditions yielding the corresponding pyrazolo[1,2-a]pyrazoles in good yields. The methodology can be extended to other 1-aryl-substituted pyrazolidinones which undergo endocyclic oxidation deriving the corresponding pyrazolones as single products.
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34

Li, Jin-Heng, De-Lie An, and Jing-Hao Qin. "Recent Advances in Cycloaddition Reactions with Alkynes to Construct Heterocycles." Synthesis 52, no. 24 (October 13, 2020): 3818–36. http://dx.doi.org/10.1055/s-0040-1707355.

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Heterocyclic compounds, especially N-heterocycles and O-heterocycles, are prominent structural motifs present in numerous natural products and medically and/or economically important compounds. This review aims to describe the development of transition-metal-catalyzed cycloaddition reactions of functionalized m-atom partners with alkynes to access a wide range of five-, six-, and seven-membered heterocycles, that is functionalized N-heterocycles and O-heterocycles such as azepines, isoquinolines, isocoumarins, spiroheterocycles, indoles, furans, and pyrroles, in a selectively controlled manner with an emphasis on scope and limitations and with a discussion of the mechanisms.1 Introduction2 Intermolecular Cycloaddition To Construct Azepine Derivatives2.1 [5+2] Cycloaddition2.2 [3+2+2] Cycloaddition2.3 [3+2]/[5+2] Cycloaddition3 Intermolecular [4+2] Cycloaddition To Construct Isoquinolines or Isocoumarins4 Intermolecular [3+2] Cycloaddition To Construct Spirohetero­cyclic Compounds, Indoles, Furans, and Pyrroles5 Summary and Outlook
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35

Wang, Kaixuan, Chaoran Xu, Xinyue Hu, Yuqiao Zhou, Lili Lin, and Xiaoming Feng. "Catalytic asymmetric [3+2] cycloaddition of isomünchnones with methyleneindolinones." Chemical Communications 57, no. 71 (2021): 8917–20. http://dx.doi.org/10.1039/d1cc03685h.

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36

Motornov, Vladimir A., Andrey A. Tabolin, Yulia V. Nelyubina, Valentine G. Nenajdenko, and Sema L. Ioffe. "Copper-catalyzed [3 + 2]-cycloaddition of α-halonitroalkenes with azomethine ylides: facile synthesis of multisubstituted pyrrolidines and pyrroles." Organic & Biomolecular Chemistry 19, no. 15 (2021): 3413–27. http://dx.doi.org/10.1039/d1ob00146a.

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37

Liu, Wentong, Yi Kuang, Zhifan Wang, Jin Zhu, and Yuanhua Wang. "Dirhodium(II)-catalyzed [3 + 2] cycloaddition of N-arylaminocyclopropane with alkyne derivatives." Beilstein Journal of Organic Chemistry 15 (February 25, 2019): 542–50. http://dx.doi.org/10.3762/bjoc.15.48.

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Dirhodium(II) complex-catalyzed [3 + 2] reactions between N-arylaminocyclopropanes and alkyne derivatives are described. The cycloaddition products proved to be versatile synthetic intermediates. trans-Cyclic β-amino acids and derivatives thereof can be conveniently synthesized using this cycloaddition protocol.
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38

Ahmad, Dalla Tiezza, and Orian. "In Silico Acetylene [2+2+2] Cycloadditions Catalyzed by Rh/Cr Indenyl Fragments." Catalysts 9, no. 8 (August 9, 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 = (C5H5)−, cyclopentadienyl anion) and IndRh, were included in the analysis. The active center is the rhodium nucleus, where the [2+2+2] cycloaddition occurs. The coordination of the Cr(CO)3 group, which may be in syn or anti conformation, affects the energetics of the catalytic cycle as well as the mechanism. The reaction and activation energies and the turnover frequency (TOF) of the catalytic cycles are rationalized, and, in agreement with the experimental findings, our computational analysis reveals that the presence of the second metal favors the catalysis.
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Kaladevi, Selvam, Arumugam Thirupathi, Jeyaraman Sridhar, and Shanmugam Muthusubramanian. "Copper catalysed [3 + 2] cycloaddition with concomitant annulation: formation of 2,4-diaryl-1,4-oxazepan-7-ones via a ketenimine route." RSC Adv. 4, no. 71 (2014): 37526–28. http://dx.doi.org/10.1039/c4ra08008d.

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40

Kafka, Stanislav, Sylvia Hauke, Arjana Salcinovic, Otto Soidinsalo, Damijana Urankar, and Janez Kosmrlj. "Copper(I)-Catalyzed [ 3+ 2] Cycloaddition of 3-Azidoquinoline-2,4(1H,3H)-diones with Terminal Alkynes." Molecules 16, no. 5 (May 18, 2011): 4070–81. http://dx.doi.org/10.3390/molecules16054070.

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41

Gulías, Moisés, Fernando López, and José L. Mascareñas. "Development of transition-metal-catalyzed cycloaddition reactions leading to polycarbocyclic systems." Pure and Applied Chemistry 83, no. 3 (February 7, 2011): 495–506. http://dx.doi.org/10.1351/pac-con-10-10-23.

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We present a compilation of methodologies developed in our laboratories to assemble polycyclic structures containing small- and medium-sized cycles, relying on the use of transition-metal-catalyzed (TMC) cycloadditions. First, we discuss the use of alkylidenecyclopropanes (ACPs) as 3C-atom partners, in particular in their Pd-catalyzed (3 + 2) cycloadditions with alkynes, alkenes, and allenes, reactions that lead to cyclopentane-containing polycyclic products in excellent yields. Then, we present the expansion of this chemistry to a (4 + 3) annulation with conjugated dienes, and to inter- and intramolecular (3 + 2 + 2) cycloadditions using external alkenes as additional 2C-π-systems. These reactions allow the preparation of different types of polycyclic structures containing cycloheptene rings, the topology of the products depending on the use of Pd or Ni catalysts. Finally, we include our more recent discoveries on the development of (4 + 3) and (4 + 2) intramolecular cyclo-additions of allenes and dienes, promoted by Pt and Au catalysts, and discuss mechanistic insights supported by experimental and density functional theory (DFT) calculations. An enantioselective version of the (4 + 2) cycloaddition with phosphoramidite Au(I) catalysts is also presented.
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42

Zhang, Ronghua, Bing Xu, Zhanming Zhang, and Junliang Zhang. "Ming-Phos/Copper(I)-Catalyzed Asymmetric[3+2] Cycloaddition of Azomethine Ylides with Nitroalkenes." Acta Chimica Sinica 78, no. 3 (2020): 245. http://dx.doi.org/10.6023/a20010019.

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Han, Jiao, You-Wei Xu, Xue-Ming Wang, Lei Zhang, and Xiang-Ping Hu. "Copper-catalyzed formal propargylic [3 + 2] cycloaddition for stereoselective construction of (E)-β-pyrazolylacrylates." Tetrahedron Letters 61, no. 3 (January 2020): 151409. http://dx.doi.org/10.1016/j.tetlet.2019.151409.

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Díez-González, Silvia, Andrea Correa, Luigi Cavallo, and Steven P. Nolan. "(NHC)Copper(I)-Catalyzed [3+2] Cycloaddition of Azides and Mono- or Disubstituted Alkynes." Chemistry - A European Journal 12, no. 29 (October 5, 2006): 7558–64. http://dx.doi.org/10.1002/chem.200600961.

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Liang, Wenbin, Kazunari Nakajima, Ken Sakata, and Yoshiaki Nishibayashi. "Copper‐Catalyzed [3+2] Cycloaddition Reactions of Isocyanoacetates with Phosphaalkynes to Prepare 1,3‐Azaphospholes." Angewandte Chemie International Edition 58, no. 4 (January 21, 2019): 1168–73. http://dx.doi.org/10.1002/anie.201812779.

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Liang, Wenbin, Kazunari Nakajima, Ken Sakata, and Yoshiaki Nishibayashi. "Copper‐Catalyzed [3+2] Cycloaddition Reactions of Isocyanoacetates with Phosphaalkynes to Prepare 1,3‐Azaphospholes." Angewandte Chemie 131, no. 4 (December 21, 2018): 1180–85. http://dx.doi.org/10.1002/ange.201812779.

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47

Gu, Shaojin, Jiehao Du, Jingjing Huang, Huan Xia, Ling Yang, Weilin Xu, and Chunxin Lu. "Bi- and trinuclear copper(I) complexes of 1,2,3-triazole-tethered NHC ligands: synthesis, structure, and catalytic properties." Beilstein Journal of Organic Chemistry 12 (May 3, 2016): 863–73. http://dx.doi.org/10.3762/bjoc.12.85.

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A series of copper complexes (3–6) stabilized by 1,2,3-triazole-tethered N-heterocyclic carbene ligands have been prepared via simple reaction of imidazolium salts with copper powder in good yields. The structures of bi- and trinuclear copper complexes were fully characterized by NMR, elemental analysis (EA), and X-ray crystallography. In particular, [Cu2(L2)2](PF6)2 (3) and [Cu2(L3)2](PF6)2 (4) were dinuclear copper complexes. Complexes [Cu3(L4)2](PF6)3 (5) and [Cu3(L5)2](PF6)3 (6) consist of a triangular Cu3 core. These structures vary depending on the imidazolium backbone and N substituents. The copper–NHC complexes tested are highly active for the Cu-catalyzed azide–alkyne cycloaddition (CuAAC) reaction in an air atmosphere at room temperature in a CH3CN solution. Complex 4 is the most efficient catalyst among these polynuclear complexes in an air atmosphere at room temperature.
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Yang, Xin-He, Jian-Ping Li, Dong-Chao Wang, Ming-Sheng Xie, Gui-Rong Qu, and Hai-Ming Guo. "Enantioselective dearomative [3+2] cycloaddition of 2-nitrobenzofurans with aldehyde-derived Morita–Baylis–Hillman carbonates." Chemical Communications 55, no. 62 (2019): 9144–47. http://dx.doi.org/10.1039/c9cc04542b.

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Liu, Suna, Pu Yang, Shiyong Peng, Chenghao Zhu, Shengyu Cao, Jian Li, and Jiangtao Sun. "Gold-catalyzed sequential annulations towards 3,4-fused bi/tri-cyclic furans involving a [3+2+2]-cycloaddition." Chemical Communications 53, no. 6 (2017): 1152–55. http://dx.doi.org/10.1039/c6cc09154g.

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50

Jaiswal, Manish K., Bhuvnesh Singh, Shreemoyee De, Neetu Singh, and Ravi P. Singh. "Stereoselective formal [3 + 3] annulation of 3-alkylidene-2-oxindoles with β,γ-unsaturated α-keto esters." Organic & Biomolecular Chemistry 18, no. 48 (2020): 9852–62. http://dx.doi.org/10.1039/d0ob02046j.

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1,4-Diazabicyclo[2.2.2]octane (DABCO)-catalyzed [3 + 3] cycloaddition reaction of 3-alkylidene-2-oxindole and β,γ-unsaturated α-keto esters under mild reaction conditions afforded the spirocyclohexene-oxindole with excellent diastereoselectivity.
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