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Journal articles on the topic 'Oxidative arylation'

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Published: 7 July 2024
Last updated: 7 July 2024

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1

Zhou, Yao, Ya Wang, Zhiyi Song, Tamaki Nakano, and Qiuling Song. "Cu-catalyzed C–N bond cleavage of 3-aminoindazoles for the C–H arylation of enamines." Organic Chemistry Frontiers 7, no. 1 (2020): 25–29. http://dx.doi.org/10.1039/c9qo01177c.

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2

Wei, Xiao-Hong, Gang-Wei Wang, and Shang-Dong Yang. "Enantioselective synthesis of arylglycine derivatives by direct C–H oxidative cross-coupling." Chemical Communications 51, no. 5 (2015): 832–35. http://dx.doi.org/10.1039/c4cc07361d.

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A new method for the synthesis of chiral α-amino acid derivatives by enantioselective C–H arylation of N-aryl glycine esters with aryl boric acids by direct C–H oxidative cross-coupling has been performed. This work successfully integrates the direct C–H oxidation with asymmetric arylation and exhibits excellent enantioselectivity.
3

Park, Soo J., Jason R. Price, and Matthew H. Todd. "Oxidative Arylation of Isochroman." Journal of Organic Chemistry 77, no. 2 (December 29, 2011): 949–55. http://dx.doi.org/10.1021/jo2021373.

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4

Yu, Congjun, and Frederic W. Patureau. "Regioselective Oxidative Arylation of Fluorophenols." Angewandte Chemie International Edition 58, no. 51 (October 31, 2019): 18530–34. http://dx.doi.org/10.1002/anie.201910352.

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5

Singh, Keisham. "Recent Advances in C–H Bond Functionalization with Ruthenium-Based Catalysts." Catalysts 9, no. 2 (February 12, 2019): 173. http://dx.doi.org/10.3390/catal9020173.

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The past decades have witnessed rapid development in organic synthesis via catalysis, particularly the reactions through C–H bond functionalization. Transition metals such as Pd, Rh and Ru constitute a crucial catalyst in these C–H bond functionalization reactions. This process is highly attractive not only because it saves reaction time and reduces waste,but also, more importantly, it allows the reaction to be performed in a highly region specific manner. Indeed, several organic compounds could be readily accessed via C–H bond functionalization with transition metals. In the recent past, tremendous progress has been made on C–H bond functionalization via ruthenium catalysis, including less expensive but more stable ruthenium(II) catalysts. The ruthenium-catalysed C–H bond functionalization, viz. arylation, alkenylation, annulation, oxygenation, and halogenation involving C–C, C–O, C–N, and C–X bond forming reactions, has been described and presented in numerous reviews. This review discusses the recent development of C–H bond functionalization with various ruthenium-based catalysts. The first section of the review presents arylation reactions covering arylation directed by N–Heteroaryl groups, oxidative arylation, dehydrative arylation and arylation involving decarboxylative and sp3-C–H bond functionalization. Subsequently, the ruthenium-catalysed alkenylation, alkylation, allylation including oxidative alkenylation and meta-selective C–H bond alkylation has been presented. Finally, the oxidative annulation of various arenes with alkynes involving C–H/O–H or C–H/N–H bond cleavage reactions has been discussed.
6

Hata, Kazuhiro, Hideto Ito, Yasutomo Segawa, and Kenichiro Itami. "Pyridylidene ligand facilitates gold-catalyzed oxidative C–H arylation of heterocycles." Beilstein Journal of Organic Chemistry 11 (December 28, 2015): 2737–46. http://dx.doi.org/10.3762/bjoc.11.295.

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Triaryl-2-pyridylidene effectively facilitates the gold-catalyzed oxidative C–H arylation of heteroarenes with arylsilanes as a unique electron-donating ligand on gold. The employment of the 2-pyridylidene ligand, which is one of the strongest electron-donating N-heterocyclic carbenes, resulted in the rate acceleration of the C–H arylation reaction of heterocycles over conventional ligands such as triphenylphosphine and a classical N-heterocyclic carbene. In situ observation and isolation of the 2-pyridylidene-gold(III) species, as well as a DFT study, indicated unusual stability of gold(III) species stabilized by strong electron donation from the 2-pyridylidene ligand. Thus, the gold(I)-to-gold(III) oxidation process is thought to be facilitated by the highly electron-donating 2-pyridylidene ligand.
7

Chen, Wei W., Nahiane Pipaon Fernández, Marta Díaz Baranda, Anton Cunillera, Laura G. Rodríguez, Alexandr Shafir, and Ana B. Cuenca. "Exploring benzylic gem-C(sp3)–boron–silicon and boron–tin centers as a synthetic platform." Chemical Science 12, no. 31 (2021): 10514–21. http://dx.doi.org/10.1039/d1sc01741a.

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This work explores divergent reactivity of the benzylic gem-boron–silicon and boron–tin double nucleophiles, including the arylation of the C–B bond with Ar–Cl, along with a complementary oxidative λ3-iodane-guided arylation of the C–Si/Sn moiety.
8

Ho, Nga Kim T., Beate Neumann, Hans-Georg Stammler, Vitor H. Menezes da Silva, Daniel G. Watanabe, Ataualpa A. C. Braga, and Rajendra S. Ghadwal. "Nickel-catalysed direct C2-arylation of N-heterocyclic carbenes." Dalton Transactions 46, no. 36 (2017): 12027–31. http://dx.doi.org/10.1039/c7dt03099a.

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Direct C2-arylation of NHCs to C2-arylated imidazolium salts (III) is achieved using Ni-catalysis. The dinuclear Ni(i) species I undergoes oxidative addition with ArX to give the Ni(ii) intermediate II. Reductive elimination delivers the arylation product III and regenerates the catalyst I.
9

Chen, Kai, Xin Li, Shuo-Qing Zhang, and Bing-Feng Shi. "Palladium-catalyzed C(sp3)–H arylation of lactic acid: efficient synthesis of chiral β-aryl-α-hydroxy acids." Organic Chemistry Frontiers 3, no. 2 (2016): 204–8. http://dx.doi.org/10.1039/c5qo00319a.

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10

Querard, Pierre, Inna Perepichka, Eli Zysman-Colman, and Chao-Jun Li. "Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst." Beilstein Journal of Organic Chemistry 12 (December 6, 2016): 2636–43. http://dx.doi.org/10.3762/bjoc.12.260.

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This report describes a highly enantioselective oxidative sp3 C–H arylation of N-aryltetrahydroisoquinolines (THIQs) through a dual catalysis platform. The combination of the photoredox catalyst, [Ir(ppy)2(dtbbpy)]PF6, and chiral copper catalysts provide a mild and highly effective sp3 C–H asymmetric arylation of THIQs.
11

Yuan, Jin-Wei, Wei-Jie Li, Liang-Ru Yang, Pu Mao, and Yong-Mei Xiao. "Regioselective C-3 arylation of coumarins with arylhydrazines via radical oxidation by potassium permanganate." Zeitschrift für Naturforschung B 71, no. 11 (November 1, 2016): 1115–23. http://dx.doi.org/10.1515/znb-2016-0109.

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AbstractAn efficient protocol for oxidative C-3 arylation of coumarins with arylhydrazine has been developed using potassium permanganate as an oxidant. The arylated coumarins with different electronic properties were obtained in moderate to good yields. The developed protocol for direct C-3 arylation of coumarins could be extended to quinolinones.
12

Park, Soo J., Jason R. Price, and Matthew H. Todd. "ChemInform Abstract: Oxidative Arylation of Isochroman." ChemInform 43, no. 21 (April 26, 2012): no. http://dx.doi.org/10.1002/chin.201221135.

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13

Faradhiyani, Alanna, Qiao Zhang, Keisuke Maruyama, Junpei Kuwabara, Takeshi Yasuda, and Takaki Kanbara. "Synthesis of bithiazole-based semiconducting polymers via Cu-catalysed aerobic oxidative coupling." Materials Chemistry Frontiers 2, no. 7 (2018): 1306–9. http://dx.doi.org/10.1039/c7qm00584a.

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14

Bu, Meijie, Teng Fei Niu, and Chun Cai. "Visible-light-mediated oxidative arylation of vinylarenes under aerobic conditions." Catalysis Science & Technology 5, no. 2 (2015): 830–34. http://dx.doi.org/10.1039/c4cy01523a.

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15

Shen, Xianfu, Yongyun Zhou, Yongkai Xi, Jingfeng Zhao, and Hongbin Zhang. "Copper catalyzed sequential arylation−oxidative dimerization of o-haloanilides: synthesis of dimeric HPI alkaloids." Chemical Communications 51, no. 80 (2015): 14873–76. http://dx.doi.org/10.1039/c5cc05378a.

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16

Jiang, Huanfeng, Wanfei Yang, Huoji Chen, Jianxiao Li, and Wanqing Wu. "Palladium-catalyzed aerobic oxidative allylic C–H arylation of alkenes with polyfluorobenzenes." Chem. Commun. 50, no. 54 (2014): 7202–4. http://dx.doi.org/10.1039/c4cc02023e.

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17

Ghosh, Asim Kumar, Sadhanendu Samanta, Payel Ghosh, Sukanya Neogi, and Alakananda Hajra. "Regioselective hydroarylation and arylation of maleimides with indazoles via a Rh(iii)-catalyzed C–H activation." Organic & Biomolecular Chemistry 18, no. 16 (2020): 3093–97. http://dx.doi.org/10.1039/d0ob00353k.

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18

Chen, Lijun, Lin Ju, Katelyn A. Bustin, and Jessica M. Hoover. "Copper-catalyzed oxidative decarboxylative C–H arylation of benzoxazoles with 2-nitrobenzoic acids." Chemical Communications 51, no. 81 (2015): 15059–62. http://dx.doi.org/10.1039/c5cc06645j.

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19

GUO, HAN, and YING XUE. "THEORETICAL STUDY ON CUI-CATALYZED LIGAND-FREE N-ARYLATION OF IMIDAZOLE WITH BROMOBENZENE." Journal of Theoretical and Computational Chemistry 11, no. 05 (October 2012): 1135–47. http://dx.doi.org/10.1142/s0219633612500757.

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The density functional theory (DFT) is used to investigate the mechanism of ligand-free CuI -catalyzed N -arylation of imidazole with aryl halide. The oxidative addition/reductive elimination mechanism is adopted via two different pathways to form the same Cu(III) intermediate. Comparing two pathways, the path 1 in which the imidazolyl coordination occurs prior to the oxidative addition is more favorable, because the free energy barrier of the rate-limiting step of path 1 is lower than the barrier of the other. In addition, it leads to a relative stable intermediate which can promote the reaction to process via path 1. And the overall free energy barrier of oxidative addition to imidazole-ligated Cu(I) complex is not high enough when comparing with the diamine-promote process, which can further prove that the N -arylation of imidazole is feasible in the absence of additional ligands. Nucleophile coordination and reductive elimination steps are facile, while the oxidative addition is the rate-limiting step.
20

Jiang, Tuo, Andreas K. Å. Persson, and Jan-E. Bäckvall. "Palladium-Catalyzed Oxidative Carbocyclization/Arylation of Enallenes." Organic Letters 13, no. 21 (November 4, 2011): 5838–41. http://dx.doi.org/10.1021/ol202451f.

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21

Lee, Kathleen S., and Joseph M. Ready. "Titanium-Mediated Oxidative Arylation of Homoallylic Alcohols." Angewandte Chemie International Edition 50, no. 9 (January 25, 2011): 2111–14. http://dx.doi.org/10.1002/anie.201007244.

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22

Lee, Kathleen S., and Joseph M. Ready. "Titanium-Mediated Oxidative Arylation of Homoallylic Alcohols." Angewandte Chemie 123, no. 9 (January 25, 2011): 2159–62. http://dx.doi.org/10.1002/ange.201007244.

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23

Huang, Guanghao, Lin Lu, Huanfeng Jiang, and Biaolin Yin. "Aerobic oxidative α-arylation of furans with boronic acids via Pd(ii)-catalyzed C–C bond cleavage of primary furfuryl alcohols: sustainable access to arylfurans." Chemical Communications 53, no. 90 (2017): 12217–20. http://dx.doi.org/10.1039/c7cc07111f.

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24

Fan, Jian, Li Li, Jitan Zhang, and Meihua Xie. "Expeditious synthesis of phenanthridines through a Pd/MnO2-mediated C–H arylation/oxidative annulation cascade from aldehydes, aryl iodides and amino acids." Chemical Communications 56, no. 18 (2020): 2775–78. http://dx.doi.org/10.1039/d0cc00300j.

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25

Luo, Haiqing, Qi Xie, Kai Sun, Jianbo Deng, Lin Xu, Kejun Wang, and Xuzhong Luo. "Rh(iii)-catalyzed C-7 arylation of indolines with arylsilanes via C–H activation." RSC Advances 9, no. 32 (2019): 18191–95. http://dx.doi.org/10.1039/c9ra04142g.

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26

Araneo, Silvia, Francesca Fontana, Francesco Minisci, Francesco Recupero, and Anna Serri. "Hydroperoxides as pseudohalides: oxidation, oxidative alkylation, acylation and arylation of acrylonitrile." Journal of the Chemical Society, Chemical Communications, no. 14 (1995): 1399. http://dx.doi.org/10.1039/c39950001399.

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27

Chen, Xin, Yunyun Bian, Baichuan Mo, Peng Sun, Chunxia Chen, and Jinsong Peng. "Copper(ii)-catalyzed synthesis of multisubstituted indoles through sequential Chan–Lam and cross-dehydrogenative coupling reactions." RSC Advances 10, no. 42 (2020): 24830–39. http://dx.doi.org/10.1039/d0ra04592f.

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28

Yuan, Jin-Wei, Liang-Ru Yang, Pu Mao, and Ling-Bo Qu. "AgNO3-catalyzed direct C–H arylation of quinolines by oxidative decarboxylation of aromatic carboxylic acids." Organic Chemistry Frontiers 4, no. 4 (2017): 545–54. http://dx.doi.org/10.1039/c6qo00533k.

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29

Morimoto, Koji, Yusuke Ohnishi, Daichi Koseki, Akira Nakamura, Toshifumi Dohi, and Yasuyuki Kita. "Stabilized pyrrolyl iodonium salts and metal-free oxidative cross-coupling." Organic & Biomolecular Chemistry 14, no. 38 (2016): 8947–51. http://dx.doi.org/10.1039/c6ob01764a.

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We have developed a direct oxidative C–H bond arylation of pyrroles with various aromatic compounds via stabilized pyrrolyl iodonium(iii) salts generated from modified hypervalent iodine(iii) and TMSCl as an activator.
30

Terai, Seiya, Yuki Sato, Takuya Kochi, and Fumitoshi Kakiuchi. "Efficient synthesis of 3,6,13,16-tetrasubstituted-tetrabenzo[a,d,j,m]coronenes by selective C–H/C–O arylations of anthraquinone derivatives." Beilstein Journal of Organic Chemistry 16 (March 31, 2020): 544–50. http://dx.doi.org/10.3762/bjoc.16.51.

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An efficient synthesis of tetrabenzo[a,d,j,m]coronene derivatives having alkyl and alkoxy substituents at the 3, 6, 13, and 16-positions was achieved based on the ruthenium-catalyzed coupling reactions of anthraquinone derivatives with arylboronates via C–H and C–O bond cleavage. The reaction sequence involving the arylation, carbonyl methylenation, and oxidative cyclization effectively provided various tetrabenzo[a,d,j,m]coronenes in short steps from readily available starting materials. Tetrabenzo[a,d,j,m]coronenes possessing two different types of substituents were obtained selectively by sequential chemoselective C–O arylation and C–H arylation. The 1H NMR spectra of the tetrabenzo[a,d,j,m]coronene product indicated its self-assembling behavior in CDCl3.
31

Nareddy, Pradeep, Frank Jordan, and Michal Szostak. "Ruthenium(ii)-catalyzed ortho-C–H arylation of diverse N-heterocycles with aryl silanes by exploiting solvent-controlled N-coordination." Organic & Biomolecular Chemistry 15, no. 22 (2017): 4783–88. http://dx.doi.org/10.1039/c7ob00818j.

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We report the first method for the direct, regioselective Ru(ii)-catalyzed oxidative arylation of C–H bonds in diverse N-heterocycles with aryl silanes by exploiting solvent-controlled N-coordination.
32

Laha, Joydev K., Shubhra Sharma, Rohan A. Bhimpuria, Neetu Dayal, Gurudutt Dubey, and Prasad V. Bharatam. "Integration of oxidative arylation with sulfonyl migration: one-pot tandem synthesis of densely functionalized (NH)-pyrroles." New Journal of Chemistry 41, no. 17 (2017): 8791–803. http://dx.doi.org/10.1039/c7nj01709j.

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A one-pot synthesis of 2-aryl-3-alkyl/aryl-sulfonyl-(NH)-pyrroles from N-sulfonylpyrroles, developed for the first time, via palladium-catalyzed oxidative C-2 arylation followed by sulfonyl migration is described.
33

Rodriguez, Jessica, Abdallah Zeineddine, E. Daiann Sosa Carrizo, Karinne Miqueu, Nathalie Saffon-Merceron, Abderrahmane Amgoune, and Didier Bourissou. "Catalytic Au(i)/Au(iii) arylation with the hemilabile MeDalphos ligand: unusual selectivity for electron-rich iodoarenes and efficient application to indoles." Chemical Science 10, no. 30 (2019): 7183–92. http://dx.doi.org/10.1039/c9sc01954e.

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The ability of the MeDalphos ligand to trigger oxidative addition of iodoarenes preferentially electron-rich, to gold has been thoroughly studied and exploited to develop an efficient Au(i)/Au(iii)-catalysed C3-arylation of indoles.
34

Zhang, Shuyao, Xiaohan Ye, Lukasz Wojtas, Wenyan Hao, and Xiaodong Shi. "Electrochemical gold redox catalysis for selective oxidative arylation." Green Synthesis and Catalysis 2, no. 1 (February 2021): 82–86. http://dx.doi.org/10.1016/j.gresc.2021.01.008.

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35

Volla, Chandra M. R., and Jan-E. Bäckvall. "Palladium-Catalyzed Oxidative Domino Carbocyclization–Arylation of Bisallenes." ACS Catalysis 6, no. 10 (August 29, 2016): 6398–402. http://dx.doi.org/10.1021/acscatal.6b02070.

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36

Basnet, Prakash, Melissa B. Sebold, Charles E. Hendrick, and Marisa C. Kozlowski. "Copper Catalyzed Oxidative Arylation of Tertiary Carbon Centers." Organic Letters 22, no. 24 (December 2, 2020): 9524–28. http://dx.doi.org/10.1021/acs.orglett.0c03581.

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37

Wolf, C., and R. Lerebours. "Arylation and Oxidative Esterification of Aldehydes with Siloxanes." Synfacts 2006, no. 12 (December 2006): 1277. http://dx.doi.org/10.1055/s-2006-955616.

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38

Bagnell, Laurence, Ulf Kreher, and Christopher R. Strauss. "Pd-catalysed arylation of propan-1-ol and derivatives: oxidative role of the arylating agent." Chemical Communications, no. 1 (2001): 29–30. http://dx.doi.org/10.1039/b005323f.

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39

Matsumoto, Takaya, and Hajime Yoshida. "Oxidative Arylation of Ethylene with Benzene to Produce Styrene." Chemistry Letters 29, no. 9 (September 2000): 1064–65. http://dx.doi.org/10.1246/cl.2000.1064.

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40

Vershinin, Vlada, Alina Dyadyuk, and Doron Pappo. "Iron-catalyzed selective oxidative arylation of phenols and biphenols." Tetrahedron 73, no. 26 (June 2017): 3660–68. http://dx.doi.org/10.1016/j.tet.2017.03.094.

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41

Kapłon, Katarzyna, Oleg M. Demchuk, Marta Wieczorek, and K. Michał Pietrusiewicz. "Brönsted acid catalyzed direct oxidative arylation of 1,4-naphthoquinone." Current Chemistry Letters 3, no. 1 (2013): 23–36. http://dx.doi.org/10.5267/j.ccl.2013.10.001.

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42

Cai, Chun, Jie Feng, Guoping Lu, and Meifang Lv. "Palladium(II)-Catalyzed Oxidative ortho-Arylation of 2-Phenylpyridines." Synlett 24, no. 16 (August 21, 2013): 2153–59. http://dx.doi.org/10.1055/s-0033-1339516.

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43

Hofer, Manuel, Alexandre Genoux, Roopender Kumar, and Cristina Nevado. "Gold-Catalyzed Direct Oxidative Arylation with Boron Coupling Partners." Angewandte Chemie International Edition 56, no. 4 (December 21, 2016): 1021–25. http://dx.doi.org/10.1002/anie.201610457.

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44

Hofer, Manuel, Alexandre Genoux, Roopender Kumar, and Cristina Nevado. "Gold-Catalyzed Direct Oxidative Arylation with Boron Coupling Partners." Angewandte Chemie 129, no. 4 (December 21, 2016): 1041–45. http://dx.doi.org/10.1002/ange.201610457.

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45

Lee, Kathleen S., and Joseph M. Ready. "ChemInform Abstract: Titanium-Mediated Oxidative Arylation of Homoallylic Alcohols." ChemInform 42, no. 24 (May 19, 2011): no. http://dx.doi.org/10.1002/chin.201124090.

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46

Zhang, Rui, Qin Xu, Kai Chen, Peng Gu, and Min Shi. "Gold-Catalyzed Cascade Oxidative Cyclization and Arylation of Allenoates." European Journal of Organic Chemistry 2013, no. 32 (September 24, 2013): 7366–71. http://dx.doi.org/10.1002/ejoc.201300896.

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47

Jiang, Tuo, Andreas K. Aa Persson, and Jan-E. Baeckvall. "ChemInform Abstract: Palladium-Catalyzed Oxidative Carbocyclization/Arylation of Enallenes." ChemInform 43, no. 12 (February 23, 2012): no. http://dx.doi.org/10.1002/chin.201212049.

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48

ARANEO, S., F. FONTANA, F. MINISCI, F. RECUPERO, and A. SERRI. "ChemInform Abstract: Hydroperoxides as Pseudohalides: Oxidation, Oxidative Alkylation, Acylation and Arylation of Acrylonitrile." ChemInform 26, no. 48 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199548077.

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49

Maurya, Sundaram, Sandip B. Jadhav, and Rambabu Chegondi. "Metal-free oxidative formal C(sp2)–H arylation of cyclopentene-1,3-diones with β-naphthols." Organic & Biomolecular Chemistry 20, no. 10 (2022): 2059–63. http://dx.doi.org/10.1039/d2ob00156j.

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50

Hong, Fenglin, Nannan Lu, Beili Lu, and Jiajia Cheng. "Synthesis of Fused Heterocycles via One-pot Oxidative O-Arylation, Pd-Catalyzed C(sp3)-H Arylation." Advanced Synthesis & Catalysis 359, no. 19 (August 21, 2017): 3299–303. http://dx.doi.org/10.1002/adsc.201700761.

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