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Journal articles on the topic 'Radical cascade'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Lynch, Dylan M., and Eoin M. Scanlan. "Thiyl Radicals: Versatile Reactive Intermediates for Cyclization of Unsaturated Substrates." Molecules 25, no. 13 (2020): 3094. http://dx.doi.org/10.3390/molecules25133094.

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Sulfur centered radicals are widely employed in chemical synthesis, in particular for alkene and alkyne hydrothiolation towards thioether bioconjugates. The steadfast radical chain process that enables efficient hydrothiolation has been explored in the context of cascade reactions to furnish complex molecular architectures. The use of thiyl radicals offers a much cheaper and less toxic alternative to the archetypal organotin-based radical methods. This review outlines the development of thiyl radicals as reactive intermediates for initiating carbocyclization cascades. Key developments in casca

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2

Rinderhagen, Heiko, and Jochen Mattay. "Synthetic Applications in Radical/Radical Cationic Cascade Reactions." Chemistry - A European Journal 10, no. 4 (2004): 851–74. http://dx.doi.org/10.1002/chem.200304827.

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3

Bowman, W. Russell, Peter T. Stephenson, and Adrian R. Young. "Cascade radical cyclisations of imines." Tetrahedron 52, no. 35 (1996): 11445–62. http://dx.doi.org/10.1016/0040-4020(96)00636-9.

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4

Quiclet-Sire, Béatrice, and Samir Z. Zard. "Some aspects of radical cascade and relay reactions." Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences 473, no. 2200 (2017): 20160859. http://dx.doi.org/10.1098/rspa.2016.0859.

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The ability to create carbon–carbon bonds is at the heart of organic synthesis. Radical processes are particularly apt at creating such bonds, especially in cascade or relay sequences where more than one bond is formed, allowing for a rapid assembly of complex structures. In the present brief overview, examples taken from the authors' laboratory will serve to illustrate the strategic impact of radical-based approaches on synthetic planning. Transformations involving nitrogen-centred radicals, electron transfer from metallic nickel and the reversible degenerative exchange of xanthates will be p

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5

Wu, Chuan-Shuo, Rong Li, Qi-Qiang Wang, and Luo Yang. "Fe-Catalyzed decarbonylative alkylation–peroxidation of alkenes with aliphatic aldehydes and hydroperoxide under mild conditions." Green Chemistry 21, no. 2 (2019): 269–74. http://dx.doi.org/10.1039/c8gc02834f.

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Decarbonylation at 60–80 °C! Readily available linear/branched aliphatic aldehydes were decarbonylated into 1°, 2° and 3° alkyl radicals at low temperature for cascade radical insertion and radical–radical coupling to construct C(sp<sup>3</sup>)–C(sp<sup>3</sup>) and C(sp<sup>3</sup>)–O bonds.

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6

Bowman, W. Russell, Martin O. Cloonan, Anthony J. Fletcher, and Tobias Stein. "Synthesis of heteroarenes using cascade radical cyclisation via iminyl radicals." Organic & Biomolecular Chemistry 3, no. 8 (2005): 1460. http://dx.doi.org/10.1039/b501509j.

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7

Bowman, W. Russell, Colin F. Bridge, Philip Brookes, Martin O. Cloonan, and David C. Leach. "ChemInform Abstract: Cascade Radical Synthesis of Heteroarenes via Iminyl Radicals." ChemInform 33, no. 21 (2010): no. http://dx.doi.org/10.1002/chin.200221163.

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8

Santagostino, Marco, and Jeremy D. Kilburn. "Cascade radical reactions of methylenecyclopropane derivatives." Tetrahedron Letters 35, no. 47 (1994): 8863–66. http://dx.doi.org/10.1016/s0040-4039(00)78518-2.

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9

Pattenden, Gerald, and Paul Wiedenau. "Cascade radical cyclisations with vinylcyclopropane electrophores." Tetrahedron Letters 38, no. 20 (1997): 3647–50. http://dx.doi.org/10.1016/s0040-4039(97)00691-6.

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10

Huang, Huan-Ming, Monserrat H. Garduño-Castro, Charlotte Morrill, and David J. Procter. "Catalytic cascade reactions by radical relay." Chemical Society Reviews 48, no. 17 (2019): 4626–38. http://dx.doi.org/10.1039/c8cs00947c.

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11

Miyabe, H., Y. Takemoto, R. Asada, and A. Toyoda. "Cascade Radical Addition-Cyclization-Trapping Reactions." Synfacts 2006, no. 12 (2006): 1249. http://dx.doi.org/10.1055/s-2006-949498.

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12

Bogen, Stéphane, Louis Fensterbank, and Max Malacria. "Unprecedented Radical Cyclizations Cascade Leading to Bicyclo[3.1.1]Heptanes. Toward a New Generation of Radical Cascades." Journal of the American Chemical Society 119, no. 21 (1997): 5037–38. http://dx.doi.org/10.1021/ja9702879.

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13

Cuadros, Sara, Matthew A. Horwitz, Bertrand Schweitzer-Chaput, and Paolo Melchiorre. "A visible-light mediated three-component radical process using dithiocarbamate anion catalysis." Chemical Science 10, no. 21 (2019): 5484–88. http://dx.doi.org/10.1039/c9sc00833k.

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A three-component radical process is reported that, by coupling alkyl chlorides, maleimides, and heteroaromatic fragments, installs multiple biologically relevant heterocycles within complex cascade products. This method, which generates radicals via an S<sub>N</sub>2-based photochemical catalytic mechanism, activates substrates incompatible with or inert to classical radical-generating strategies.

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14

Peng, Xiang, Ren-Xiang Liu, Xiang-Yan Xiao, and Luo Yang. "Fe-catalyzed Decarbonylative Alkylative Spirocyclization of N-Arylcinnamamides: Access to Alkylated 1-Azaspirocyclohexadienones." Molecules 25, no. 3 (2020): 432. http://dx.doi.org/10.3390/molecules25030432.

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For the convenient introduction of simple linear/branched alkyl groups into biologically important azaspirocyclohexadienones, a practical Fe-catalyzed decarbonylative cascade spiro-cyclization of N-aryl cinnamamides with aliphatic aldehydes to provide alkylated 1-azaspiro-cyclohexadienones was developed. Aliphatic aldehydes were oxidative decarbonylated into primary, secondary and tertiary alkyl radicals conveniently and allows for the subsequent cascade construction of dual C(sp3)-C(sp3) and C=O bonds via radical addition, spirocyclization and oxidation sequence.

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15

Landais, Yannick, and Edouard Godineau. "Synthesis of Piperidinones through a Radical Cascade." Synthesis 2009, no. 15 (2009): 2646–49. http://dx.doi.org/10.1055/s-0029-1216860.

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16

Donald, James R., and Sophie L. Berrell. "Radical cyanomethylation via vinyl azide cascade-fragmentation." Chemical Science 10, no. 22 (2019): 5832–36. http://dx.doi.org/10.1039/c9sc01370a.

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17

Miyabe, Hideto, Ryuta Asada, Akira Toyoda, and Yoshiji Takemoto. "Enantioselective Cascade Radical Addition–Cyclization–Trapping Reactions." Angewandte Chemie International Edition 45, no. 35 (2006): 5863–66. http://dx.doi.org/10.1002/anie.200602042.

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18

BOWMAN, W. R., P. T. STEPHENSON, and A. R. YOUNG. "ChemInform Abstract: Cascade Radical Cyclizations of Imines." ChemInform 27, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.199652056.

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19

Miyabe, Hideto, Ryuta Asada, Akira Toyoda, and Yoshiji Takemoto. "Enantioselective Cascade Radical Addition–Cyclization–Trapping Reactions." Angewandte Chemie 118, no. 35 (2006): 5995–98. http://dx.doi.org/10.1002/ange.200602042.

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20

Huang, Hanchu, Wenqi Wang, Zefeng Zhou, et al. "Radical Ring-Closing/Ring-Opening Cascade Polymerization." Journal of the American Chemical Society 141, no. 32 (2019): 12493–97. http://dx.doi.org/10.1021/jacs.9b05568.

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21

Wang, Xiaobei. "Indole Alkaloid Synthesis via Radical Cascade Reactions." Chem 2, no. 6 (2017): 749–50. http://dx.doi.org/10.1016/j.chempr.2017.05.012.

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22

Wille, Uta. "ChemInform Abstract: Intermolecular Radical Additions to Alkynes: Cascade-type Radical Cyclizations." ChemInform 42, no. 19 (2011): no. http://dx.doi.org/10.1002/chin.201119230.

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23

Stademann, Arne, and Uta Wille. "NO3• Induced Self-Terminating Radical Oxygenations: Diastereoselective Synthesis of Anellated Pyrrolidines." Australian Journal of Chemistry 57, no. 11 (2004): 1055. http://dx.doi.org/10.1071/ch04124.

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Anellated pyrrolidines 19–22 were obtained through a diastereoselective self-terminating, oxidative radical cyclization cascade by treating the cis-cyclopentyl substituted alkynyl amines 14–18 with photochemically generated nitrate radicals, NO3●. A fast and modular access to the starting materials 14–18 was developed, which readily enables variation of the substitution pattern at the pyrrolidine ring formed upon radical cyclization. The diastereoselectivity of this reaction sequence was found to be strongly influenced by the nature of the substituents at the nitrogen atom. This shows that a c

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24

Yu, Kaili, Minyan Li, Guogang Deng, et al. "An Efficient Route to Isochromene Derivatives via Cascade Radical Cyclization and Radical‐Radical Coupling." Advanced Synthesis & Catalysis 361, no. 18 (2019): 4354–59. http://dx.doi.org/10.1002/adsc.201900497.

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25

Guin, Joyram, Promita Biswas та Subhasis Paul. "Synthesis of 3,3-Dialkylated Oxindoles by Oxidative Radical 1,2-Alkylarylation of α,β-Unsaturated Amides". Synlett 28, № 11 (2017): 1244–49. http://dx.doi.org/10.1055/s-0036-1588754.

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3,3-Dialkylated oxindoles (1,3-dihydro-2H-indol-2-ones), particularly those containing C3 quaternary stereogenic centers, occupy an important place in organic synthesis and drug discovery. The radical 1,2-alkylarylation of activated olefins with alkyl radicals has emerged as the most atom- and step-economical approach to 3,3-dialkylated oxindoles. This article covers important developments in the area of oxidative radical alkylation/cyclization cascade reactions of α,β-unsaturated amides toward the synthesis of alkyl-substituted oxindoles by employing a range of alkyl-radical precursors and va

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26

Ishibashi, Hiroyuki, Atsuko Ishita та Osamu Tamura. "Radical cascade involving a 5-endo-trig cyclization of α-amidoyl radicals". Tetrahedron Letters 43, № 3 (2002): 473–75. http://dx.doi.org/10.1016/s0040-4039(01)02200-6.

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27

Miyabe, Hideto, Ryuta Asada, and Yoshiji Takemoto. "Cascade radical reaction of substrates with a carbon–carbon triple bond as a radical acceptor." Beilstein Journal of Organic Chemistry 9 (June 13, 2013): 1148–55. http://dx.doi.org/10.3762/bjoc.9.128.

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The limitation of hydroxamate ester as a chiral Lewis acid coordination moiety was first shown in an intermolecular reaction involving a radical addition and sequential allylation processes. Next, the effect of hydroxamate ester was studied in the cascade addition–cyclization–trapping reaction of substrates with a carbon–carbon triple bond as a radical acceptor. When substrates with a methacryloyl moiety and a carbon–carbon triple bond as two polarity-different radical acceptors were employed, the cascade reaction proceeded effectively. A high level of enantioselectivity was also obtained by a

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28

Péter, Áron, and David J. Procter. "Cascades, Catalysis and Chiral Ligand Control with SmI2; The Rebirth of a Reagent." CHIMIA International Journal for Chemistry 74, no. 1 (2020): 18–22. http://dx.doi.org/10.2533/chimia.2020.18.

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This review focuses on recent developments from our laboratory in the field of radical reactions mediated by the archetypal reductive single electron transfer (SET) reagent, SmI2. Namely, we have expanded the scope of reducible carbonyl moieties to esters and amides and have exploited the resultant ketyl radicals in radical cascade reactions that generate unprecedented scaffolds. Moreover, we have taken the first steps to address the long-standing challenges of catalysis and chiral ligand control associated with the reagent.

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29

Ali, Amjad, David C. Harrowven, and Gerald Pattenden. "Cascade cobalt group transfer - radical trapping - tandem radical cyclisation reactions in synthesis." Tetrahedron Letters 33, no. 20 (1992): 2851–54. http://dx.doi.org/10.1016/s0040-4039(00)78877-0.

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30

Miyazaki, Koichiro, Yu Yamane, Ryuichiro Yo, Hidemitsu Uno, and Akio Kamimura. "Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction." Beilstein Journal of Organic Chemistry 9 (July 4, 2013): 1326–32. http://dx.doi.org/10.3762/bjoc.9.149.

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Bicyclodihydrosiloles were readily prepared from optically active enyne compounds by a radical cascade reaction triggered by tris(trimethylsilyl)silane ((Me3Si)3SiH). The reaction was initiated by the addition of a silyl radical to an α,β-unsaturated ester, forming an α-carbonyl radical that underwent radical cyclization to a terminal alkyne unit. The resulting vinyl radical attacked the silicon atom in an SHi manner to give dihydrosilole. The reaction preferentially formed trans isomers of bicyclosiloles with an approximately 7:3 to 9:1 selectivity.

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31

Liao, Jianhua, Xiao Yang, Lu Ouyang, Yinlong Lai, Jiuzhong Huang, and Renshi Luo. "Recent advances in cascade radical cyclization of radical acceptors for the synthesis of carbo- and heterocycles." Organic Chemistry Frontiers 8, no. 6 (2021): 1345–63. http://dx.doi.org/10.1039/d0qo01453b.

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32

Li, Xiaoqing, Xiangsheng Xu, Zhi Wang, Xiaoyu Yan, Xiaoxue He та Xinhuan Yan. "Iminyl-Radical-Mediated Cyanoalkylarylation of Activated Alkenes Enabled by Silver-Catalyzed Decarboxylation of α-Imino Oxy Acids". Synlett 31, № 08 (2020): 809–12. http://dx.doi.org/10.1055/s-0039-1691595.

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An iminyl-radical-mediated cyanoalkylarylation of α,β-unsaturated imides with cyclic α-imino oxy acids leading to isoquinoline-1,3(2H,4H)-dione derivatives has been developed. The procedure involves the generation of iminyl radicals through silver-catalyzed oxidative decarboxylation, followed by a C–C bond cleavage, cyanoalkylation, and C–H-functionalization cascade.

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33

Hu, Zhang, Si-dong Li, and Peng-zhi Hong. "Intramolecular cascade radical cyclizations promoted by samarium diiodide." Arkivoc 2010, no. 9 (2010): 171–77. http://dx.doi.org/10.3998/ark.5550190.0011.916.

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34

Ishibashi, Hiroyuki, Masatake Inomata, Masashi Ohba, and Masazumi Ikeda. "Stereoselective radical cascade approach to benzo[a]quinolizidines." Tetrahedron Letters 40, no. 6 (1999): 1149–52. http://dx.doi.org/10.1016/s0040-4039(98)02550-7.

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35

Ryu, Ilhyong, Yoshitaka Uenoyama, and Takahide Fukuyama. "Cascade Radical Carbonylations Leading to 3-Substituted Cyclohexanones." Synlett 2006, no. 14 (2006): 2342–44. http://dx.doi.org/10.1055/s-2006-949643.

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36

PATTENDEN, G., and P. WIEDENAU. "ChemInform Abstract: Cascade Radical Cyclizations with Vinylcyclopropane Electrophores." ChemInform 28, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.199735038.

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37

SANTAGOSTINO, M., and J. D. KILBURN. "ChemInform Abstract: Cascade Radical Reactions of Methylenecyclopropane Derivatives." ChemInform 26, no. 16 (1995): no. http://dx.doi.org/10.1002/chin.199516051.

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38

Bennasar, M. Lluïsa, Tomàs Roca, Rosa Griera, and Joan Bosch. "New Cascade 2-Indolylacyl Radical Addition−Cyclization Reactions." Journal of Organic Chemistry 66, no. 22 (2001): 7547–51. http://dx.doi.org/10.1021/jo015905p.

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39

Taniguchi, Tsuyoshi, and Hiroyuki Ishibashi. "Short Synthesis of (−)-Cephalotaxine Using a Radical Cascade." Organic Letters 10, no. 18 (2008): 4129–31. http://dx.doi.org/10.1021/ol801747m.

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40

Miyabe, Hideto, Yoshiji Takemoto, and Akira Toyoda. "Enantioselective Cascade Radical Addition-Cyclization of Oxime Ethers." Synlett 2007, no. 12 (2007): 1885–88. http://dx.doi.org/10.1055/s-2007-984530.

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41

Miyabe, Hideto, Eito Yoshioka, Xin Wang, and Shigeru Kohtani. "Cascade Radical Reaction Induced by Polarity-Mismatched Perfluoroalkylation." Synlett 2011, no. 14 (2011): 2085–89. http://dx.doi.org/10.1055/s-0030-1261167.

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42

Shang, Wenbin, Chunyu Zhu, Fengyuan Peng, Zhiqiang Pan, Yuzhen Ding, and Chengfeng Xia. "Nitrogen-Centered Radical-Mediated Cascade Amidoglycosylation of Glycals." Organic Letters 23, no. 4 (2021): 1222–27. http://dx.doi.org/10.1021/acs.orglett.0c04178.

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43

Brachet, Etienne, Leyre Marzo, Mohamed Selkti, Burkhard König, and Philippe Belmont. "Visible light amination/Smiles cascade: access to phthalazine derivatives." Chemical Science 7, no. 8 (2016): 5002–6. http://dx.doi.org/10.1039/c6sc01095d.

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We report the synthesis of various phthalazines via a new cascade reaction, initiated by visible light photocatalysis, involving a radical hydroamination reaction followed by a radical Smiles rearrangement.

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44

Miao, Pannan, Ruining Li, Xianfeng Lin, Liangming Rao, and Zhankui Sun. "Visible-light induced metal-free cascade Wittig/hydroalkylation reactions." Green Chemistry 23, no. 4 (2021): 1638–41. http://dx.doi.org/10.1039/d1gc00091h.

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Through a relay olefination and radical addition process, we developed cascade Wittig/hydroalkylation reactions induced by visible light. This metal-free radical approach features mild conditions, robustness, and excellent functionality tolerance.

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45

Xuan, Jun, Dario Gonzalez-Abradelo, Cristian Alejandro Strassert, Constantin-Gabriel Daniliuc, and Armido Studer. "Radical Cascade Cyclization: Reaction of 1,6-Enynes with Aryl Radicals by Electron Catalysis." European Journal of Organic Chemistry 2016, no. 29 (2016): 4961–64. http://dx.doi.org/10.1002/ejoc.201601033.

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46

Li, Long, Guoliang Shang, and Wei Qin. "Label-free polymerization amplified potentiometric sensing platform for radical reactions using polyion sensitive membrane electrodes as transducers." RSC Advances 6, no. 42 (2016): 35628–32. http://dx.doi.org/10.1039/c6ra04530h.

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47

Zhao, Quan-Qing, Jun Chen, Dong-Mei Yan, Jia-Rong Chen, and Wen-Jing Xiao. "Photocatalytic Hydrazonyl Radical-Mediated Radical Cyclization/Allylation Cascade: Synthesis of Dihydropyrazoles and Tetrahydropyridazines." Organic Letters 19, no. 13 (2017): 3620–23. http://dx.doi.org/10.1021/acs.orglett.7b01609.

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48

Miyabe, Hideto, Ryuta Asada, and Yoshiji Takemoto. "Lewis acid-mediated radical cyclization: stereocontrol in cascade radical addition–cyclization–trapping reactions." Organic & Biomolecular Chemistry 10, no. 17 (2012): 3519. http://dx.doi.org/10.1039/c2ob25073j.

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49

Yuan, Jing-Mei, Jinnan Li, Heyang Zhou, et al. "Synthesis of 3-sulfonylquinolines by visible-light promoted metal-free cascade cycloaddition involving N-propargylanilines and sodium sulfinates." New Journal of Chemistry 44, no. 8 (2020): 3189–93. http://dx.doi.org/10.1039/c9nj05248h.

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50

Barrett, Anthony, Tsz-Kan Ma, and Thomas Mies. "Recent Developments in Polyene Cyclizations and Their Applications in Natural Product Synthesis." Synthesis 51, no. 01 (2018): 67–82. http://dx.doi.org/10.1055/s-0037-1610382.

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Cascade polyene cyclization reactions are highly efficient and elegant bioinspired transformations that involve simultaneous multiple bond constructions to rapidly generate complex polycyclic molecules. This review summarizes the most prominent work on a variety of cationic and radical cascade cyclizations and their applications in natural product synthesis published between 2014 and 2018.1 Introduction2 Cationic Polyene Cyclizations2.1 Lewis Acid Mediated Polyene Cyclizations2.2 Brønsted Acid Mediated Polyene Cyclizations2.3 Halogen Electrophile Initiated Polyene Cyclizations2.4 Sulfur Electr

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