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Journal articles on the topic 'Oxidative alkenylation'

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Published: 7 July 2024
Last updated: 7 July 2024

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1

Koubachi, Jamal, Nabil El Brahmi, Gérald Guillaumet, and Saïd El Kazzouli. "Oxidative Alkenylation of Fused Bicyclic Heterocycles." European Journal of Organic Chemistry 2019, no. 15 (April 1, 2019): 2568–86. http://dx.doi.org/10.1002/ejoc.201900199.

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2

Sunke, Rajnikanth, Vimal Kumar, Mohd Ashraf Ashfaq, Swapna Yellanki, Raghavender Medisetti, Pushkar Kulkarni, E. V. Venkat Shivaji Ramarao, Nasreen Z. Ehtesham, and Manojit Pal. "A Pd(ii)-catalyzed C–H activation approach to densely functionalized N-heteroaromatics related to neocryptolepine and their evaluation as potential inducers of apoptosis." RSC Advances 5, no. 56 (2015): 44722–27. http://dx.doi.org/10.1039/c5ra06764b.

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3

Cao, Hao, Dong Liu, Chao Liu, Xinquan Hu, and Aiwen Lei. "Copper-catalyzed oxidative alkenylation of thioethers via Csp3–H functionalization." Organic & Biomolecular Chemistry 13, no. 8 (2015): 2264–66. http://dx.doi.org/10.1039/c4ob02564d.

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4

Tang, Jingjie, Mei Cong, Yi Xia, Gilles Quéléver, Yuting Fan, Fanqi Qu, and Ling Peng. "Pd-catalyzed oxidative C–H alkenylation for synthesizing arylvinyltriazole nucleosides." Organic & Biomolecular Chemistry 13, no. 1 (2015): 110–14. http://dx.doi.org/10.1039/c4ob01836b.

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5

Mishra, Neeraj Kumar, Jihye Park, Satyasheel Sharma, Sangil Han, Mirim Kim, Youngmi Shin, Jinbong Jang, Jong Hwan Kwak, Young Hoon Jung, and In Su Kim. "Direct access to isoindolines through tandem Rh(iii)-catalyzed alkenylation and cyclization of N-benzyltriflamides." Chem. Commun. 50, no. 18 (2014): 2350–52. http://dx.doi.org/10.1039/c3cc49486a.

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6

Katsina, Tania, Elissavet E. Anagnostaki, Foteini Mitsa, Vasiliki Sarli, and Alexandros L. Zografos. "Palladium-catalyzed direct alkenylation of 4-hydroxy-2-pyridones." RSC Advances 6, no. 9 (2016): 6978–82. http://dx.doi.org/10.1039/c5ra26360c.

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7

Miyasaka, Mitsuru, Koji Hirano, Tetsuya Satoh, and Masahiro Miura. "Palladium-Catalyzed Direct Oxidative Alkenylation of Azoles." Journal of Organic Chemistry 75, no. 15 (August 6, 2010): 5421–24. http://dx.doi.org/10.1021/jo101214y.

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8

Zhu, Weihao, and T. Brent Gunnoe. "Advances in Rhodium-Catalyzed Oxidative Arene Alkenylation." Accounts of Chemical Research 53, no. 4 (April 2, 2020): 920–36. http://dx.doi.org/10.1021/acs.accounts.0c00036.

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9

Cao, Hua, Sai Lei, Jinqiang Liao, Jianping Huang, Huifang Qiu, Qinlin Chen, Shuxian Qiu, and Yaoyi Chen. "Palladium(ii)-catalyzed intermolecular oxidative C-3 alkenylations of imidazo[1,2-a]pyridines by substrate-contolled regioselective C–H functionalization." RSC Adv. 4, no. 91 (2014): 50137–40. http://dx.doi.org/10.1039/c4ra09669j.

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An efficient and highly regioselective palladium(ii)-catalyzed oxidative C-3 alkenylation of imidazo[1,2-a]pyridines with acrylate, acrylonitrile, or vinylarenes has been developed by using oxygen as an oxidant.
10

Tang, Shan, Yong Wu, Wenqing Liao, Ruopeng Bai, Chao Liu, and Aiwen Lei. "Revealing the metal-like behavior of iodine: an iodide-catalysed radical oxidative alkenylation." Chem. Commun. 50, no. 34 (2014): 4496–99. http://dx.doi.org/10.1039/c4cc00644e.

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11

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.
12

Chen, Weiqiang, Hui-Jing Li, Qin-Ying Li, and Yan-Chao Wu. "Direct oxidative coupling of N-acyl pyrroles with alkenes by ruthenium(ii)-catalyzed regioselective C2-alkenylation." Organic & Biomolecular Chemistry 18, no. 3 (2020): 500–513. http://dx.doi.org/10.1039/c9ob02421b.

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13

Qiu, Youai, Alexej Scheremetjew, and Lutz Ackermann. "Electro-Oxidative C–C Alkenylation by Rhodium(III) Catalysis." Journal of the American Chemical Society 141, no. 6 (January 12, 2019): 2731–38. http://dx.doi.org/10.1021/jacs.8b13692.

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14

Li, Jie, Christoph Kornhaaß, and Lutz Ackermann. "Ruthenium-catalyzed oxidative C–H alkenylation of aryl carbamates." Chemical Communications 48, no. 92 (2012): 11343. http://dx.doi.org/10.1039/c2cc36196e.

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15

Jiao, Lin-Yu, and Martin Oestreich. "Oxidative Palladium(II)-Catalyzed C-7 Alkenylation of Indolines." Organic Letters 15, no. 20 (October 8, 2013): 5374–77. http://dx.doi.org/10.1021/ol402687t.

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16

Kang, Dongjin, Jaeyoung Cho, and Phil Ho Lee. "Palladium-catalyzed direct C-3 oxidative alkenylation of phosphachromones." Chemical Communications 49, no. 89 (2013): 10501. http://dx.doi.org/10.1039/c3cc45874a.

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17

Miyasaka, Mitsuru, Koji Hirano, Tetsuya Satoh, and Masahiro Miura. "ChemInform Abstract: Palladium-Catalyzed Direct Oxidative Alkenylation of Azoles." ChemInform 41, no. 50 (November 18, 2010): no. http://dx.doi.org/10.1002/chin.201050131.

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18

Lah, Hafiz Ul, Faheem Rasool, and Syed Khalid Yousuf. "Palladium catalyzed C(sp2)–C(sp2) bond formation. A highly regio- and chemoselective oxidative Heck C-3 alkenylation of pyrones and pyridones." RSC Advances 5, no. 96 (2015): 78958–61. http://dx.doi.org/10.1039/c5ra12631b.

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Palladium catalysed ligand free highly regio- and chemoselective dehydrogenative C-3 alkenylation of pyrones and unprotected pyridones from unactivated alkenes is reported. Simple reaction conditions and broad substrate scope make the process useful.
19

Li, Yu-An, Ge Wu, and Jia Li. "Palladium-Catalyzed N-Alkenylation of N-Aryl Phosphoramidates with Alkenes." Molecules 28, no. 11 (May 31, 2023): 4466. http://dx.doi.org/10.3390/molecules28114466.

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Versatile and concise Pd-catalyzed oxidative N-alkenylation of N-aryl phosphoramidates with alkenes is described in this study, a reaction that is of great significance but surprisingly unexploited. The transformation proceeds under mild reaction conditions, using O2 as a green oxidant and TBAB as an effective additive. An efficient catalytic system allows a variety of drug-related substrates to participate in these transformations, which is of great interest in the drug discovery and development of phosphoramidates.
20

Tian, Yunfei, Luping Zheng, Ying Chen, Yufei Li, Mengna Wang, Weijun Fu, and Zejiang Li. "Ferrous Salt-Catalyzed Oxidative Alkenylation of Indoles: Facile Access to 3-Alkylideneindolin-2-Ones." Catalysts 13, no. 6 (May 25, 2023): 930. http://dx.doi.org/10.3390/catal13060930.

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The direct oxidative alkenylation of indoles is achieved by ferrous salts under mild conditions, which provides one effective strategy for the synthesis of 3-alkylideneindolin-2-one in a single step. This reaction system features simple and readily available materials, mild conditions, and easy accessibility. The control experiments also demonstrate a radical pathway was involved in the reaction. Moreover, the method performs well on the gram-scale experiment, which indicates that this method enjoys a broad prospect in synthetic chemistry.
21

Kang, Dongjin, Jaeyoung Cho, and Phil Ho Lee. "ChemInform Abstract: Palladium-Catalyzed Direct C-3 Oxidative Alkenylation of Phosphachromones." ChemInform 45, no. 11 (February 27, 2014): no. http://dx.doi.org/10.1002/chin.201411200.

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22

Jiao, Lin-Yu, and Martin Oestreich. "ChemInform Abstract: Oxidative Palladium(II)-Catalyzed C-7 Alkenylation of Indolines." ChemInform 45, no. 13 (March 14, 2014): no. http://dx.doi.org/10.1002/chin.201413114.

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23

Li, Jie, Christoph Kornhaass, and Lutz Ackermann. "ChemInform Abstract: Ruthenium-Catalyzed Oxidative C-H Alkenylation of Aryl Carbamates." ChemInform 44, no. 13 (March 18, 2013): no. http://dx.doi.org/10.1002/chin.201313030.

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24

Lu, Nan, Chengxia Miao, and Xiaozheng Lan. "Theoretical investigation on Rh(III)-catalyzed switchable C–H alkenylation of enamide with enone and Rh(I)-catalyzed decarbonylative version of 1,2,3,4-tetrahydroquinoline with anhydride." Thermal Science and Engineering 7, no. 1 (July 1, 2024): 6267. http://dx.doi.org/10.24294/tse.v7i1.6267.

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The mechanism is investigated for Rh(III)-catalyzed C-H alkenylation of enamide with enone and Rh(I)-catalyzed decarbonylative version of 1,2,3,4-tetrahydroquinoline with anhydride. The former contains β-C(sp2)−H activation of enamide, 1,2-migratory insertion of enone, β-hydride elimination or protodemetalation with additional HCl. The diastereoselectivity is kinetically controlled favoring alkenylation N-(2Z,4E)-butadiene while the regio-divergence is switchable to alkylation. The latter is composed of rate-limiting oxidative addition of anhydride to Rh(I), C8-selective C–H activation after ligand exchange producing tBuCO2H and six-membered rhodacycle, decarbonylation releasing CO as new carboxylate ligand and reductive elimination of Rh-alkenyl precursor leading to C8-alkenylated product. The whole process with huge heat release is favorable thermodynamically and all barriers capable to overcome under microwave assistance. The positive solvation effect is suggested by decreased absolute and activation energies in solution compared with in gas. These results are supported by Multiwfn analysis on FMO composition of specific TSs, and MBO value of vital bonding, breaking.
25

Kim, Namhoon, Minsik Min, and Sungwoo Hong. "Regioselective palladium(ii)-catalyzed aerobic oxidative Heck-type C3 alkenylation of sulfocoumarins." Organic Chemistry Frontiers 2, no. 12 (2015): 1621–24. http://dx.doi.org/10.1039/c5qo00294j.

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An efficient method for the direct C–H olefination of sulfocoumarins with a wide range of alkenes is developed. Moreover, O2 was successfully utilized as the sole oxidant for the oxidative Heck reaction. This approach enables the rapid generation of various 3-alkenylated sulfocoumarins.
26

Lessi, Marco, Attilio Nania, Melania Pittari, Laura Lodone, Angela Cuzzola, and Fabio Bellina. "Palladium-Catalyzed Dehydrogenative C-2 Alkenylation of 5-Arylimidazoles and Related Azoles with Styrenes." Catalysts 11, no. 7 (June 23, 2021): 762. http://dx.doi.org/10.3390/catal11070762.

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The construction of carbon–carbon bonds by direct involvement of two unactivated carbon–hydrogen bonds, without any directing group, ensures a high atom economy of the entire process. Here, we describe a simple protocol for the Pd(II)/Cu(II)-promoted intermolecular cross-dehydrogenative coupling (CDC) of 5-arylimidazoles, benzimidazoles, benzoxazole and 4,5-diphenylimidazole at their C-2 position with functionalized styrenes. This specific CDC, known as the Fujiwara–Moritani reaction or oxidative Heck coupling, also allowed the C-4 alkenylation of the imidazole nucleus when both 2 and 5 positions were occupied.
27

Berteina-Raboin, Sabine, Jamal Koubachi, Abderrahim Mouaddib, and Gérald Guillaumet. "Pd/Cu-Catalyzed Oxidative C-H Alkenylation of Imidazo[1,2-a]pyridines." Synthesis 2009, no. 02 (December 12, 2008): 271–76. http://dx.doi.org/10.1055/s-0028-1083252.

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28

Zhang, Guangling, Ziyuan Li, Yue Huang, Jinyi Xu, Xiaoming Wu, and Hequan Yao. "Direct C3-alkenylation of pyridin-4(1H)-one via oxidative Heck coupling." Tetrahedron 69, no. 3 (January 2013): 1115–19. http://dx.doi.org/10.1016/j.tet.2012.11.061.

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29

Tang, Jingjie, Mei Cong, Yi Xia, Gilles Quelever, Yuting Fan, Fanqi Qu, and Ling Peng. "ChemInform Abstract: Pd-Catalyzed Oxidative C-H Alkenylation for Synthesizing Arylvinyltriazole Nucleosides." ChemInform 46, no. 21 (May 2015): no. http://dx.doi.org/10.1002/chin.201521235.

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30

Sun, Peng, Jiaojiao Yang, Zirui Song, Yichao Cai, Yajie Liu, Chunxia Chen, Xin Chen, and Jinsong Peng. "Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction." Synthesis 52, no. 01 (November 5, 2019): 75–84. http://dx.doi.org/10.1055/s-0039-1690240.

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Starting from simple anilines and ester arylpropiolates, an efficient one-pot synthesis of 2-arylindole-3-carboxylate derivatives has been developed through copper-mediated sequential hydroamination and cross-dehydrogenative coupling (CDC) reaction. The initial hydroamination of anilines to ester arylpropiolates in benzene can proceed in a stereoselective manner to give ester (Z)-3-(arylamino)acrylates in the presence of CuCl2/phenanthroline, KMnO4, and KHCO3 at 120 °C. Sequentially, these in situ functionalized adducts can undergo direct intramolecular oxidative alkenylation of aromatic C–H bond in mixed solvents (benzene/DMSO 1:1) at 130 °C affording multi-substituted­ indoles in good to high yields.
31

Sawant, Devesh, Ram Pardasani, Iqubal Singh, Gaurav Tulsyan, and Kishor Abbagani. "Ruthenium-Catalyzed Oxidative C–H Bond Alkenylation of 2-Phenylimidazo[1,2-a]pyridine." Synlett 26, no. 12 (May 21, 2015): 1671–76. http://dx.doi.org/10.1055/s-0034-1380746.

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32

Kozhushkov, Sergei I., and Lutz Ackermann. "Ruthenium-catalyzed direct oxidative alkenylation of arenes through twofold C–H bond functionalization." Chem. Sci. 4, no. 3 (2013): 886–96. http://dx.doi.org/10.1039/c2sc21524a.

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33

Suzuki, Yudai, Bo Sun, Tatsuhiko Yoshino, Motomu Kanai, and Shigeki Matsunaga. "Cp∗Co(III)-catalyzed oxidative C–H alkenylation of benzamides with ethyl acrylate." Tetrahedron 71, no. 26-27 (July 2015): 4552–56. http://dx.doi.org/10.1016/j.tet.2015.02.032.

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34

Kannaboina, Prakash, K. Anil Kumar, and Parthasarathi Das. "Site-Selective Intermolecular Oxidative C-3 Alkenylation of 7-Azaindoles at Room Temperature." Organic Letters 18, no. 5 (February 4, 2016): 900–903. http://dx.doi.org/10.1021/acs.orglett.5b03429.

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35

Graczyk, Karolina, Wenbo Ma, and Lutz Ackermann. "Oxidative Alkenylation of Aromatic Esters by Ruthenium-Catalyzed Twofold C–H Bond Cleavages." Organic Letters 14, no. 16 (July 31, 2012): 4110–13. http://dx.doi.org/10.1021/ol301759v.

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36

Meng, Lingkui, Kun Wu, Chao Liu, and Aiwen Lei. "Palladium-catalysed aerobic oxidative Heck-type alkenylation of Csp3–H for pyrrole synthesis." Chemical Communications 49, no. 52 (2013): 5853. http://dx.doi.org/10.1039/c3cc42307g.

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37

Shi, Renyi, Lijun Lu, Hua Zhang, Borui Chen, Yuchen Sha, Chao Liu, and Aiwen Lei. "Palladium/Copper-Catalyzed Oxidative CH Alkenylation/N-Dealkylative Carbonylation of Tertiary Anilines." Angewandte Chemie 125, no. 40 (August 14, 2013): 10776–79. http://dx.doi.org/10.1002/ange.201303911.

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38

Vora, Harit U., Anthony P. Silvestri, Casper J. Engelin, and Jin-Quan Yu. "Rhodium(II)-Catalyzed Nondirected Oxidative Alkenylation of Arenes: Arene Loading at One Equivalent." Angewandte Chemie 126, no. 10 (January 30, 2014): 2721–24. http://dx.doi.org/10.1002/ange.201310539.

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39

Vora, Harit U., Anthony P. Silvestri, Casper J. Engelin, and Jin-Quan Yu. "Rhodium(II)-Catalyzed Nondirected Oxidative Alkenylation of Arenes: Arene Loading at One Equivalent." Angewandte Chemie International Edition 53, no. 10 (January 30, 2014): 2683–86. http://dx.doi.org/10.1002/anie.201310539.

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40

Shi, Renyi, Lijun Lu, Hua Zhang, Borui Chen, Yuchen Sha, Chao Liu, and Aiwen Lei. "Palladium/Copper-Catalyzed Oxidative CH Alkenylation/N-Dealkylative Carbonylation of Tertiary Anilines." Angewandte Chemie International Edition 52, no. 40 (August 14, 2013): 10582–85. http://dx.doi.org/10.1002/anie.201303911.

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41

Jadhav, Pankaj P., Nilesh M. Kahar, and Sudam G. Dawande. "Ruthenium(II)-Catalyzed Highly Chemo- and Regioselective Oxidative C6 Alkenylation of Indole-7-carboxamides." Organic Letters 23, no. 22 (November 1, 2021): 8673–77. http://dx.doi.org/10.1021/acs.orglett.1c02948.

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42

Anastasiou, Ioannis, Francesco Ferlin, Orlando Viteritti, Stefano Santoro, and Luigi Vaccaro. "Pd/C-catalyzed aerobic oxidative C–H alkenylation of arenes in γ-valerolactone (GVL)." Molecular Catalysis 513 (August 2021): 111787. http://dx.doi.org/10.1016/j.mcat.2021.111787.

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43

Mo, Juntae, Sujin Lim, Sangjune Park, Taekyu Ryu, Sanghyuck Kim, and Phil Ho Lee. "Oxidative ortho-alkenylation of arylphosphine oxides by rhodium-catalyzed C–H bond twofold cleavage." RSC Advances 3, no. 40 (2013): 18296. http://dx.doi.org/10.1039/c3ra43764g.

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44

Sharma, Satyasheel, Sangil Han, Youngmi Shin, Neeraj Kumar Mishra, Hyunji Oh, Jihye Park, Jong Hwan Kwak, Beom Soo Shin, Young Hoon Jung, and In Su Kim. "Rh-catalyzed oxidative C2-alkenylation of indoles with alkynes: unexpected cleavage of directing group." Tetrahedron Letters 55, no. 19 (May 2014): 3104–7. http://dx.doi.org/10.1016/j.tetlet.2014.04.001.

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45

Suzuki, Yudai, Bo Sun, Tatsuhiko Yoshino, Motomu Kanai, and Shigeki Matsunaga. "ChemInform Abstract: Cp*Co(III)-Catalyzed Oxidative C-H Alkenylation of Benzamides with Ethylacrylate." ChemInform 46, no. 42 (October 2015): no. http://dx.doi.org/10.1002/chin.201542066.

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46

Kim, Namhoon, Minsik Min, and Sungwoo Hong. "ChemInform Abstract: Regioselective Palladium(II)-Catalyzed Aerobic Oxidative Heck-Type C3 Alkenylation of Sulfocoumarins." ChemInform 47, no. 12 (March 2016): no. http://dx.doi.org/10.1002/chin.201612185.

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47

Zhang, Guangling, Ziyuan Li, Yue Huang, Jinyi Xu, Xiaoming Wu, and Hequan Yao. "ChemInform Abstract: Direct C3-Alkenylation of Pyridin-4(1H)-one via Oxidative Heck Coupling." ChemInform 44, no. 22 (May 13, 2013): no. http://dx.doi.org/10.1002/chin.201322159.

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48

Laha, Joydev K., Rohan A. Bhimpuria, and Gajanan B. Mule. "Site-Selective Oxidative C4 Alkenylation of (NH)-Pyrroles Bearing an Electron-Withdrawing C2 Group." ChemCatChem 9, no. 6 (February 24, 2017): 1092–96. http://dx.doi.org/10.1002/cctc.201601468.

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49

Martínez, Ángel Manu, Nuria Rodríguez, Ramón Gómez Arrayás, and Juan C. Carretero. "Synthesis of alkylidene pyrrolo[3,4-b]pyridin-7-one derivatives via RhIII-catalyzed cascade oxidative alkenylation/annulation of picolinamides." Chem. Commun. 50, no. 46 (2014): 6105–7. http://dx.doi.org/10.1039/c4cc02322f.

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50

Knight, Brian J., Jacob O. Rothbaum, and Eric M. Ferreira. "The design of a readily attachable and cleavable molecular scaffold for ortho-selective C–H alkenylation of arene alcohols." Chemical Science 7, no. 3 (2016): 1982–87. http://dx.doi.org/10.1039/c5sc03948g.

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