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Journal articles on the topic 'Palladium-catalyzed cascade reactions'

Author: Grafiati

Published: 4 June 2021

Last updated: 5 February 2022

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1

Della Ca’, Nicola. "Palladium-Catalyzed Reactions." Catalysts 11, no. 5 (2021): 588. http://dx.doi.org/10.3390/catal11050588.

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Palladium is probably the most versatile and exploited transition metal in catalysis due to its capability to promote a myriad of organic transformations both at laboratory and industrial scales (alkylation, arylation, cyclization, hydrogenation, oxidation, isomerization, cross-coupling, cascade, radical reactions, etc [...]

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2

Li, Jianxiao, Shaorong Yang, Wanqing Wu, and Huanfeng Jiang. "Palladium‐Catalyzed Cascade Cyclization/Alkynylation Reactions." Chemistry – An Asian Journal 14, no. 23 (2019): 4114–28. http://dx.doi.org/10.1002/asia.201901202.

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3

Ohno, Hiroaki, and Shinsuke Inuki. "Recent Progress in Palladium-Catalyzed Cascade Cyclizations for Natural Product Synthesis." Synthesis 50, no. 04 (2018): 700–710. http://dx.doi.org/10.1055/s-0036-1589165.

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Cascade reactions (also represented as domino reactions) realize the step-economical direct construction of natural product core structures. The use of atom-economical elementary reactions in cascade processes can minimize waste production and avoid prefunctionalization of the substrates. Palladium catalysis, which promotes a variety of atom-economical elementary reactions, has long been used as a powerful approach to the direct formation of complex heterocycles. In this short review, palladium-catalyzed cascade reactions for the construction of core structures of natural products reported in

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4

Odell, Luke, Mats Larhed, and Linda Åkerbladh. "Palladium-Catalyzed Molybdenum Hexacarbonyl-Mediated Gas-Free Carbonylative Reactions." Synlett 30, no. 02 (2018): 141–55. http://dx.doi.org/10.1055/s-0037-1610294.

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This account summarizes Pd(0)-catalyzed Mo(CO)6-mediated gas-free carbonylative reactions published in the period October 2011 to May 2018. Presented reactions include inter- and intramolecular carbonylations, carbonylative cross-couplings, and carbonylative multicomponent reactions using Mo(CO)6 as a solid source of CO. The presented methodologies were developed mainly for small-scale applications, avoiding the problematic use of gaseous CO in a standard laboratory. In most cases, the reported Mo(CO)6-mediated carbonylations were conducted in sealed vials or by using two-chamber solutions.1 I

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5

Comesse, Sébastien, Ismail Alahyen, Laure Benhamou, Vincent Dalla, and Catherine Taillier. "20 Years of Forging N-Heterocycles from Acrylamides through Domino/Cascade Reactions." Synthesis 53, no. 19 (2021): 3409–39. http://dx.doi.org/10.1055/a-1503-7932.

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AbstractAcrylamides are versatile building blocks that are easily obtained from readily available starting materials. During the last 20 years, these valuable substrates bearing a nucleophilic nitrogen atom and an electrophilic double bond have proven to be efficient domino partners, leading to a wide variety of complex aza-heterocycles of synthetic relevance. In this non-exhaustive review, metal-free and metal-triggered reactions followed by an annulation will be presented; these two approaches allow good modulation of the reactivity of the polyvalent acrylamides.1 Introduction2 Metal-Free An

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6

Yip, Kai-Tai, Nian-Yong Zhu, and Dan Yang. "Palladium-Catalyzed Highly Diastereoselective Oxidative Cascade Cyclization Reactions." Organic Letters 11, no. 9 (2009): 1911–14. http://dx.doi.org/10.1021/ol900355h.

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7

Yamamoto, Yoshinori, and Nitin Patil. "Palladium-Catalyzed Cascade Reactions of Highly Activated Olefins." Synlett 2007, no. 13 (2007): 1994–2005. http://dx.doi.org/10.1055/s-2007-984892.

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8

Huang, Jie, Feng Li, Lei Cui, Shikuan Su, Xueshun Jia, and Jian Li. "Palladium-catalyzed cascade reactions of enynones and isocyanides: access towards functionalized ketenimine and its application." Chemical Communications 56, no. 33 (2020): 4555–58. http://dx.doi.org/10.1039/c9cc09363j.

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9

Dodonova, Jelena, and Sigitas Tumkevicius. "Fused Pyrrolo[2,3-d]pyrimidines (7-Deazapurines) by Palladium-Catalyzed Direct N–H and C–H Arylation Reactions." Synthesis 49, no. 11 (2017): 2523–34. http://dx.doi.org/10.1055/s-0036-1588734.

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Palladium-catalyzed intramolecular direct C–H arylations for the synthesis of hitherto unknown fused hetero systems containing an incorporated pyrrolo[2,3-d]pyrimidine scaffold are described. Pyrimido[5′,4′:4,5]pyrrolo[2,1-a]isoindoles were synthesized from 2,4-diarylpyrrolo[2,3-d]pyrimidines and o-bromobenzyl bromides by using a cascade N-benzylation/C–H arylation reaction sequence. A series of pyrimido[5′,4′:4,5]pyrrolo[1,2-f]phenanthridines were successfully assembled via a domino process involving the palladium-catalyzed direct double C–H arylation reactions of 2,4,7-triarylpyrrolo[2,3-d]

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10

GRIGG, R., and V. SRIDHARAN. "ChemInform Abstract: Palladium-Catalyzed Intermolecular Cascade Cyclization-Cyclopropantion Reactions." ChemInform 24, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199318101.

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11

Blouin, Sarah, Romain Pertschi, Angèle Schoenfelder, Jean Suffert, and Gaëlle Blond. "Molecular Diversity of Cyclooctatetraenes through Palladium-Catalyzed Cascade Reactions." Advanced Synthesis & Catalysis 360, no. 11 (2018): 2166–71. http://dx.doi.org/10.1002/adsc.201800110.

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12

Sun, Wan, Chen Chen, Yuan Qi, Jinghui Zhao, Yinwei Bao, and Bolin Zhu. "Palladium-catalyzed cascade reactions of alkene-tethered carbamoyl chlorides with N-tosyl hydrazones: synthesis of alkene-functionalized oxindoles." Organic & Biomolecular Chemistry 17, no. 36 (2019): 8358–63. http://dx.doi.org/10.1039/c9ob01672d.

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13

Luo, Haofan, Zijuan Wang, Wenteng Chen, Chang He, and Guolin Zhang. "Synthesis of 2-Benzoylbenzofurans via Palladium(II)-catalyzed Cascade Reactions." Organic Preparations and Procedures International 53, no. 2 (2021): 127–37. http://dx.doi.org/10.1080/00304948.2020.1862636.

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14

Yu, Haihua, Li Xiao, Xicheng Yang, and Liming Shao. "Controllable access to multi-substituted imidazoles via palladium(ii)-catalyzed C–C coupling and C–N condensation cascade reactions." Chemical Communications 53, no. 70 (2017): 9745–48. http://dx.doi.org/10.1039/c7cc05315k.

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A novel and efficient protocol for the controllable synthesis of various di-, tri- and tetra-substituted imidazoles via cascade palladium catalyzed C–C coupling followed by intramolecular C–N bond formation was developed.

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15

Aghahosseini, Hamideh, Ali Ramazani, Farideh Gouranlou, and Sang Woo Joo. "Nanoreactors Technology in Green Organic Synthesis." Current Organic Synthesis 14, no. 6 (2017): 810–64. http://dx.doi.org/10.2174/1570179413666161008200641.

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Background: Nanoreactors technology represents a promising tool for efficient and selective organic synthesis typically under “green” and sustainable reaction conditions. These structures with generating a confined reaction environment to accommodate that both reactants and catalysts can change the reaction pathways and induce new activities and selectivities. Objective: The paper reviews literature examples in which nanoreactors were employed in various types of organic and metal catalyzed reactions including multicomponent reactions, palladium-catalyzed coupling reactions, olefin metathesis,

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16

de Meijere, Armin, Michael Schelper, Mario Knoke, et al. "Palladium-catalyzed cross-coupling reactions and electrocyclizations—efficient combinations for new cascade reactions." Journal of Organometallic Chemistry 687, no. 2 (2003): 249–55. http://dx.doi.org/10.1016/j.jorganchem.2003.07.007.

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17

HEUMANN, A., and M. REGLIER. "ChemInform Abstract: The Stereochemistry of Palladium Catalyzed Cyclization Reactions. Part 3. Cascade Reactions." ChemInform 27, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199645294.

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18

Ghosh, Tapas. "Regioselective access of alkylidendibenzo[c,f]oxocine framework via cyclocarbopalladation/cross-coupling cascade reactions and reductive Heck strategy." New Journal of Chemistry 41, no. 8 (2017): 2927–33. http://dx.doi.org/10.1039/c6nj03825e.

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Palladium-catalyzed dual strategies of cascade cyclocarbopalladation/cross-coupling of alkynes and a reductive Heck reaction have been developed to construct dibenzo[c,f]oxocine frameworks with tri- and tetra-substituted exo-cyclic alkenes with high stereo- and regio-control.

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19

Ping, Yuanyuan, Yuxiu Li, Jieping Zhu, and Wangqing Kong. "Construction of Quaternary Stereocenters by Palladium‐Catalyzed Carbopalladation‐Initiated Cascade Reactions." Angewandte Chemie 131, no. 6 (2018): 1576–87. http://dx.doi.org/10.1002/ange.201806088.

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20

Ping, Yuanyuan, Yuxiu Li, Jieping Zhu, and Wangqing Kong. "Construction of Quaternary Stereocenters by Palladium‐Catalyzed Carbopalladation‐Initiated Cascade Reactions." Angewandte Chemie International Edition 58, no. 6 (2018): 1562–73. http://dx.doi.org/10.1002/anie.201806088.

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21

GRIGG, R., P. KENNEWELL, A. TEASDALE, and V. SRIDHARAN. "ChemInform Abstract: Palladium-Catalyzed Cascade Cycloaddition Reactions. General Concepts and Illustrative Examples." ChemInform 24, no. 20 (2010): no. http://dx.doi.org/10.1002/chin.199320070.

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22

Wu, Guojiao, Yifan Deng, Haiqing Luo, Tianjiao Li, Yan Zhang та Jianbo Wang. "Palladium-Catalyzed Cascade Reactions ofα-Halo-N-Tosylhydrazones, Indoles, and Aryl Iodides". Asian Journal of Organic Chemistry 5, № 7 (2016): 874–77. http://dx.doi.org/10.1002/ajoc.201600137.

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23

FREDERICKSON, M., R. GRIGG, J. MARKANDU, and J. REDPATH. "ChemInform Abstract: Palladium(II)-Catalyzed Cascade Cyclization-Cycloaddition Reactions of Alkenyl Oximes." ChemInform 26, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199511167.

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24

Zhang, Guolin, Yongping Yu, Zijuan Wang, Wenteng Chen, Haofan Luo, and Chang He. "Cascade Reactions to Substituted 1H-Pyrrole-3-carbonitriles via Ligand-Free Palladium(II)-Catalyzed C(sp)–C(sp2) Coupling." Synthesis 52, no. 11 (2020): 1659–65. http://dx.doi.org/10.1055/s-0039-1691731.

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An efficient and simple synthesis of substituted 1H-pyrrole-3-carbonitriles was developed. This reaction is a palladium(II)-catalyzed cascade of C(sp)–C(sp2) coupling followed by intramolecular C–N bond formation. The method can tolerate various substrates with satisfactory yields. Its ligand-free conditions and high efficiency make this method particularly attractive.

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25

Blázquez-Barbadillo, C., E. Aranzamendi, E. Coya, E. Lete, N. Sotomayor, and H. González-Díaz. "Perturbation theory model of reactivity and enantioselectivity of palladium-catalyzed Heck–Heck cascade reactions." RSC Advances 6, no. 45 (2016): 38602–10. http://dx.doi.org/10.1039/c6ra08751e.

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26

Yao, Xinrong, Linjun Qi, Renhao Li та ін. "Palladium-Catalyzed Cascade Reactions of δ-Ketonitriles with Arylboronic Acids: Synthesis of Pyridines". ACS Combinatorial Science 22, № 3 (2020): 114–19. http://dx.doi.org/10.1021/acscombsci.9b00198.

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27

Gu, Zheng-Yang, Tong-Hao Zhu, Jia-Jia Cao, Xiao-Ping Xu, Shun-Yi Wang, and Shun-Jun Ji. "Palladium-Catalyzed Cascade Reactions of Isocyanides with Enaminones: Synthesis of 4-Aminoquinoline Derivatives." ACS Catalysis 4, no. 1 (2013): 49–52. http://dx.doi.org/10.1021/cs400904t.

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28

Grigg, Ronald, Angela Liu, Duncan Shaw, et al. "ChemInform Abstract: Palladium-Catalyzed Cascade Molecular Queuing-Cycloaddition, Cyclocondensation and Diels-Alder Reactions." ChemInform 31, no. 48 (2000): no. http://dx.doi.org/10.1002/chin.200048155.

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29

Oh, Chang Ho, and Young Mook Lim. "Palladium-catalyzed cascade cyclization-coupling reactions of 2-bromo-1,6-enynes with organoboronic acids." Tetrahedron Letters 44, no. 2 (2003): 267–70. http://dx.doi.org/10.1016/s0040-4039(02)02536-4.

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30

Hitce, Julien, and Olivier Baudoin. "Substituted Benzocarbocycles by Palladium-Catalyzed Cascade Reactions Featuring a C(sp3)H Activation Step." Advanced Synthesis & Catalysis 349, no. 11-12 (2007): 2054–60. http://dx.doi.org/10.1002/adsc.200700099.

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31

Li, Man‐Bo, Daniels Posevins, Antoine Geoffroy, Can Zhu, and Jan‐E Bäckvall. "Efficient Heterogeneous Palladium‐Catalyzed Oxidative Cascade Reactions of Enallenols to Furan and Oxaborole Derivatives." Angewandte Chemie International Edition 59, no. 5 (2020): 1992–96. http://dx.doi.org/10.1002/anie.201911462.

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32

Li, Man‐Bo, Daniels Posevins, Antoine Geoffroy, Can Zhu, and Jan‐E Bäckvall. "Efficient Heterogeneous Palladium‐Catalyzed Oxidative Cascade Reactions of Enallenols to Furan and Oxaborole Derivatives." Angewandte Chemie 132, no. 5 (2019): 2008–12. http://dx.doi.org/10.1002/ange.201911462.

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33

Hu, Yi-min, Jie Zhou, Xiang-tian Long, Jian-lin Han, Chen-jian Zhu, and Yi Pan. "Palladium-catalyzed cascade reactions of benzyl halides with N-allyl-N-(2-butenyl)-p-toluenesulfonamide." Tetrahedron Letters 44, no. 27 (2003): 5009–10. http://dx.doi.org/10.1016/s0040-4039(03)01177-8.

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34

Wang, Lei, Shiyong Peng, and Jian Wang. "Palladium-catalyzed cascade reactions of coumarins with alkynes: synthesis of highly substituted cyclopentadiene fused chromones." Chemical Communications 47, no. 19 (2011): 5422. http://dx.doi.org/10.1039/c1cc10939a.

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35

Ohno, Hiroaki. "Recent Advances in the Construction of Polycyclic Compounds by Palladium-Catalyzed Atom-Economical Cascade Reactions." Asian Journal of Organic Chemistry 2, no. 1 (2012): 18–28. http://dx.doi.org/10.1002/ajoc.201200128.

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36

Grigg, Ronald, Jeremy P. Major, Fionna M. Martin, and Mark Whittaker. "ChemInform Abstract: Solution and Solid-Phase Synthesis of Hydroxamic Acids via Palladium Catalyzed Cascade Reactions." ChemInform 30, no. 51 (2010): no. http://dx.doi.org/10.1002/chin.199951074.

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37

FREDERICKSON, M., R. GRIGG, M. THORNTON-PETT та J. REDPATH. "ChemInform Abstract: Palladium(II)-Catalyzed Oxime-Metallo-Nitrone-Isoxazolidine Cascade Reactions of α-Imino Aldoximes." ChemInform 29, № 9 (2010): no. http://dx.doi.org/10.1002/chin.199809132.

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38

HOLZAPFEL, C. W., and L. MARAIS. "ChemInform Abstract: Palladium-Catalyzed Cascade Reactions of Unsaturated Carbohydrate Derivatives. Synthesis of Enantiopure Tricyclic Compounds." ChemInform 29, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.199809205.

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39

Yip, Kai-Tai, and Dan Yang. "Palladium(II)-Catalyzed Oxidative Cascade Cyclization Reactions of Anilides and Anilines: Scope and Mechanistic Investigations." Chemistry - An Asian Journal 6, no. 8 (2011): 2166–75. http://dx.doi.org/10.1002/asia.201100242.

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40

Dinda, Enakshi, Samir Kumar Bhunia та Ranjan Jana. "Palladium-Catalyzed Cascade Reactions for Annulative π -Extension of Indoles to Carbazoles through C–H Bond Activation". Current Organic Chemistry 24, № 22 (2020): 2612–33. http://dx.doi.org/10.2174/1385272824999200817170058.

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The annulative &#960;-extension (APEX) reactions through C-H bond activation has tremendous potential to access fused aromatic systems from relatively simple aromatic compounds in a single step. This state-of-the-art technique has the ability to streamline the synthesis of functionalized materials useful in material science, biomedical research, agroand pharmaceutical industries. Furthermore, C-H activation strategy does not require prefunctionalization steps, which allows for the late-stage modification of the functional molecule with requisite molecular properties. Owing to their unique

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41

Cheng, Ming, Jianwei Yan, Feng Hu, Hong Chen, and Youhong Hu. "Palladium-catalyzed cascade reactions of 3-iodochromones with aryl iodides and norbornadiene leading to annulated xanthones." Chem. Sci. 4, no. 1 (2013): 526–30. http://dx.doi.org/10.1039/c2sc21335d.

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42

Coya, Estibaliz, Nuria Sotomayor, and Esther Lete. "Enantioselective Palladium-Catalyzed Heck-Heck Cascade Reactions: Ready Access to the Tetracyclic Core of Lycorane Alkaloids." Advanced Synthesis & Catalysis 357, no. 14-15 (2015): 3206–14. http://dx.doi.org/10.1002/adsc.201500431.

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43

Montgomery, Thomas D., Antoinette E. Nibbs, Ye Zhu, and Viresh H. Rawal. "Rapid Access to Spirocyclized Indolenines via Palladium-Catalyzed Cascade Reactions of Tryptamine Derivatives and Propargyl Carbonate." Organic Letters 16, no. 13 (2014): 3480–83. http://dx.doi.org/10.1021/ol501409a.

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44

Li, Ende, Xingcan Cheng, Chengyu Wang, Yushang Shao, and Yanzhong Li. "Palladium-Catalyzed Synthesis of 2,3,4-Trisubstituted Furans via Cascade Reactions of Aryloxy-enynes with Aryl Halides." Journal of Organic Chemistry 77, no. 17 (2012): 7744–48. http://dx.doi.org/10.1021/jo3012545.

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45

Hu, Langxi, Weijun Gui, Zichen Liu, and Baishan Jiang. "Synthesis of 3-aryl-2-aminoquinolines: palladium-catalyzed cascade reactions of gem-dibromovinylanilines with tert-butyl isocyanide and arylboronic acids." RSC Adv. 4, no. 72 (2014): 38258–62. http://dx.doi.org/10.1039/c4ra05670a.

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46

Lux, Michaelyn C., Melissa L. Boby, Joshua L. Brooks та Derek S. Tan. "Synthesis of bicyclic ethers by a palladium-catalyzed oxidative cyclization-redox relay-π-allyl-Pd cyclization cascade reaction". Chemical Communications 55, № 49 (2019): 7013–16. http://dx.doi.org/10.1039/c9cc03775f.

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47

Wang, Zi-Juan, Wen-Teng Chen, Chang He, Hao-Fan Luo, Guo-Lin Zhang, and Yong-Ping Yu. "Cascade reactions to 2,4-disubstituted thiazoles via ligand-free palladium(II)-catalyzed C(sp)–C(sp2) coupling." Tetrahedron 76, no. 9 (2020): 130953. http://dx.doi.org/10.1016/j.tet.2020.130953.

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48

Naidu, Veluru Ramesh, and Jan-E. Bäckvall. "Synthesis of Cross-Conjugated Polyenes via Palladium-Catalyzed Oxidative C–C Bond Forming Cascade Reactions of Allenes." Journal of Organic Chemistry 85, no. 8 (2020): 5428–37. http://dx.doi.org/10.1021/acs.joc.0c00186.

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49

Gabriele, Bartolo, Lucia Veltri, Raffaella Mancuso, and Carla Carfagna. "Cascade Reactions: A Multicomponent Approach to Functionalized Indane Derivatives by a Tandem Palladium- Catalyzed Carbamoylation/Carbocylization Process." Advanced Synthesis & Catalysis 356, no. 11-12 (2014): 2547–58. http://dx.doi.org/10.1002/adsc.201301051.

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50

Frutos-Pedreño, Roberto, and José-Antonio García-López. "2-Arylacetamides as Versatile Precursors for 3-Aminoisocoumarin and Homophthalimide Derivatives: Palladium-Catalyzed Cascade Double Carbonylation Reactions." Advanced Synthesis & Catalysis 358, no. 16 (2016): 2692–700. http://dx.doi.org/10.1002/adsc.201600224.

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