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Journal articles on the topic 'Amidyl radical'

Author: Grafiati

Published: 5 June 2025

Last updated: 2 August 2025

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1

Gaudreault, Philippe, Christian Drouin, and Jean Lessard. "First examples of intramolecular addition of primary amidyl radicals to olefins." Canadian Journal of Chemistry 83, no. 6-7 (2005): 543–45. http://dx.doi.org/10.1139/v05-029.

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The first examples of intramolecular addition of primary amidyl radicals to olefins are described. Amidyl radicals were generated from N-(phenylthio)amides in refluxing benzene using a catalytic amount of 2,2′-azobis(isobutyronitrile) (5 mol%) and tributyltin hydride (~2.2 equiv.). The resulting yields of cyclic products ranged from 63% to 85%.Key words: radical cyclization, amidyl radicals, nitrogen heterocycles.

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2

Chow, Yuan L., and Richard A. Perry. "Chemistry of amidyl radicals: intramolecular reactivities of alkenyl amidyl radicals." Canadian Journal of Chemistry 63, no. 8 (1985): 2203–10. http://dx.doi.org/10.1139/v85-362.

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Amidyl radicals possessing Δ4,5, Δ5,6, and Δ6,7 double bonds were generated from the photodecomposition of nitrosamides and chloramides and the products were identified. Dichotomies of amidyl radical reactivities were discovered and compared with published kinetic rate constants. In complete reversal to intermolecular reactivities, intramolecularly the alkenyl amidyl radicals preferentially add to the double bonds rather than abstract a C-5 hydrogen even if it is allylic. In intramolecular competition, amidyl radicals add to an acyl side chain double bond more efficiently than to an alkyl one;

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3

Hu, Qu-Ping, Yu-Tao Liu, Yong-Ze Liu, and Fei Pan. "Photoinduced remote regioselective radical alkynylation of unactivated C–H bonds." Chemical Communications 58, no. 14 (2022): 2295–98. http://dx.doi.org/10.1039/d1cc06885g.

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4

Wang, Yu-Zhao, Wu-Jie Lin, Hong-Chao Liu, and Wei Yu. "Visible-light-promoted radical amidoarylation of arylacrylamides towards amidated oxindoles." Organic Chemistry Frontiers 9, no. 8 (2022): 2164–68. http://dx.doi.org/10.1039/d2qo00127f.

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A visible-light-promoted radical amidation/cyclization of arylacrylamides was realized by using N-aminopyridinium salts as the source of amidyl radicals. A variety of amide-tethered-oxindoles were prepared in this way in moderate to good yields.

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5

Chow, Yuan L., Thomas W. Mojelsky, Leon J. Magdzinski, and M. Tichý. "Chemistry of amido radicals: intramolecular hydrogen abstraction as related to amido radical configurations." Canadian Journal of Chemistry 63, no. 8 (1985): 2197–202. http://dx.doi.org/10.1139/v85-361.

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Model bromamides were photolysed to investigate the reactivity of intramolecular C-5 hydrogen abstraction (from the nitrogen atom) of the corresponding amidyl radicals and of the cyclization of the resulting C-bromides. The observed results are discussed in terms of stereoelectronic as well as energetic considerations. In the former C-5 hydrogen abstraction, the reactivity difference between semi-rigid trans and cis-oriented reaction centers is only slightly in favor of the latter; the small difference is interpreted as due to the planar ground state Π amidyl radical structure with a low N—CO

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6

Horner, John H., Osama M. Musa, Anne Bouvier, and Martin Newcomb. "Absolute Kinetics of Amidyl Radical Reactions." Journal of the American Chemical Society 120, no. 31 (1998): 7738–48. http://dx.doi.org/10.1021/ja981244a.

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7

Huot, Jean-Yves, Denis Serve, Sylvie Desjardins, and Jean Lessard. "The electrochemical oxidation of silver and tetraethylammonium salts of formamides and imides. N,N-Coupling of formanilidyl radicals." Canadian Journal of Chemistry 66, no. 1 (1988): 35–44. http://dx.doi.org/10.1139/v88-005.

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The electrochemical oxidation of [amide-Ag-amide]Ag, [amide-Ag-amide]Et4N, and [amide]Et4N salts of imides and formanilides, in acetonitrile containing tetraethylammonium tetrafluoroborate, at platinum and vitreous carbon electrodes, is a one-electron and irreversible (αn < 1) process leading to an amidyl radicals that preferentially abstracts hydrogen from the medium to give the parent amide. N,N-Coupling (formation of hydrazine derivatives) was observed in the oxidation of the amide-Ag-amide anions of formanilide and p-methoxyformanilide. No coupling was observed in the oxidation of the a

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8

Clark, Andrew J., Robert J. Deeth, Christopher J. Samuel, and Hathaichanuk Wongtap. "Stereoselectivity in Amidyl Radical Cyclisations: Alkyl Mode Cyclisations." Synlett 1999, no. 4 (1999): 444–46. http://dx.doi.org/10.1055/s-1999-2640.

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9

Clark, Andrew J., and Joanne L. Peacock. "Stereoselectivity in amidyl radical cyclisations. Acyl mode cyclisations." Tetrahedron Letters 39, no. 33 (1998): 6029–32. http://dx.doi.org/10.1016/s0040-4039(98)01189-7.

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10

Zhang, Dongming, Bin Lv, Pan Gao, Xiaodong Jia, and Yu Yuan. "Direct C–H amination reactions of arenes with N-hydroxyphthalimides catalyzed by cuprous bromide." Beilstein Journal of Organic Chemistry 18 (June 3, 2022): 647–52. http://dx.doi.org/10.3762/bjoc.18.65.

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An efficient Cu-catalyzed strategy for the direct C–H amination of arenes in high yields using N-hydroxyphthalimide as the amidyl radical precursor under air is reported. A possible mechanism is proposed that proceeds via a radical reaction in the presence of CuBr and triethyl phosphite.

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11

Rui, Jinyan, Qun Zhao, Anthony J. Huls, et al. "Directed evolution of nonheme iron enzymes to access abiological radical-relay C(sp ³ )−H azidation." Science 376, no. 6595 (2022): 869–74. http://dx.doi.org/10.1126/science.abj2830.

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We report the reprogramming of nonheme iron enzymes to catalyze an abiological C(sp 3 )‒H azidation reaction through iron-catalyzed radical relay. This biocatalytic transformation uses amidyl radicals as hydrogen atom abstractors and Fe(III)‒N 3 intermediates as radical trapping agents. We established a high-throughput screening platform based on click chemistry for rapid evolution of the catalytic performance of identified enzymes. The final optimized variants deliver a range of azidation products with up to 10,600 total turnovers and 93% enantiomeric excess. Given the prevalence of radical r

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12

Li, Long-Hai, Yin Wei, and Min Shi. "N-Hydroxyphthalimide imidate esters as amidyl radical precursors in the visible light photocatalyzed C–H amidation of heteroarenes." Organic Chemistry Frontiers 8, no. 9 (2021): 1935–40. http://dx.doi.org/10.1039/d0qo01641a.

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N-Hydroxyphthalimide (NHPI) imidate esters were used as amidyl radical precursors in the visible light photocatalyzed C–H amidation of heteroarenes, affording the desired amidation products in moderate to good yields.

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13

Ward, Robert M., and Jennifer M. Schomaker. "Allene Trifunctionalization via Amidyl Radical Cyclization and TEMPO Trapping." Journal of Organic Chemistry 86, no. 13 (2021): 8891–99. http://dx.doi.org/10.1021/acs.joc.1c00675.

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14

Maity, Asim, Pritam Roychowdhury, Roberto G. Herrera, and David C. Powers. "Diversification of Amidyl Radical Intermediates Derived from C–H Aminopyridylation." Organic Letters 24, no. 14 (2022): 2762–66. http://dx.doi.org/10.1021/acs.orglett.2c00869.

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15

CLARK, A. J., and J. L. PEACOCK. "ChemInform Abstract: Stereoselectivity in Amidyl Radical Cyclizations. Acyl Mode Cyclizations." ChemInform 29, no. 44 (2010): no. http://dx.doi.org/10.1002/chin.199844121.

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16

Clark, Andrew J., Robert J. Deeth, Christopher J. Samuel, and Hathaichanuk Wongtap. "ChemInform Abstract: Stereoselectivity in Amidyl Radical Cyclizations: Alkyl Mode Cyclizations." ChemInform 30, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199931140.

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17

Hou, Zhong‐Wei, and Hai‐Chao Xu. "Electrochemically Enabled Intramolecular Aminooxygenation of Alkynes via Amidyl Radical Cyclization." Chinese Journal of Chemistry 38, no. 4 (2020): 394–98. http://dx.doi.org/10.1002/cjoc.201900500.

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18

Zhang, Hanyang, Wen Liu, Jiale Hu, Qian Zhang, Zeguo Fang та Dong Li. "Copper-Catalyzed Trifluoromethylthiolaton and Radical Cyclization of N-Phenylpent-4-Enamides to Construct SCF3-Substituted γ-Lactams". Catalysts 14, № 11 (2024): 797. http://dx.doi.org/10.3390/catal14110797.

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An efficient method involving copper-catalyzed trifluoromethylthiolation and radical cyclization of N-phenylpent-4-enamides using readily available and stable AgSCF3 as the trifluoromethylthiolating reagent is described. The method enables the synthesis of a series of potential medicinally valuable trifluoromethylthio-substituted γ-lactams and relative 2-oxazolidinone derivatives with broad functional group compatibility. Mechanistic investigations indicated that this reaction involved amidyl radical-initiated cascade 5-exo-trig cyclization followed by trifluoromethylthiolation, resulting in t

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19

Fong, Mei C., and Carl H. Schiesser. "Intramolecular Homolytic Substitution with Amidyl Radicals: A Free-Radical Synthesis of Ebselen and Related Analogues." Journal of Organic Chemistry 62, no. 10 (1997): 3103–8. http://dx.doi.org/10.1021/jo970019t.

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20

Clark, Andrew J., та Joanne L. Peacock. "An amidyl radical cyclisation approach towards the synthesis of β-lactams". Tetrahedron Letters 39, № 10 (1998): 1265–68. http://dx.doi.org/10.1016/s0040-4039(97)10772-9.

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21

Tang, Yu, and Chaozhong Li. "Facile 5-Endo Amidyl Radical Cyclization Promoted by Vinylic Iodine Substitution." Organic Letters 6, no. 19 (2004): 3229–31. http://dx.doi.org/10.1021/ol049052+.

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22

Hu, Tianshun, Meihua Shen, Qian Chen, and Chaozhong Li. "Pushing Radical Cyclization from Regioselective to Regiospecific: Cyclization of Amidyl Radicals Controlled by Vinylic Halogen Substitution." Organic Letters 8, no. 12 (2006): 2647–50. http://dx.doi.org/10.1021/ol060983q.

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23

Han, Guifang, Yuxiu Liu, and Qingmin Wang. "Total Synthesis of Phenanthroindolizidine Alkaloids through an Amidyl Radical Cascade/Rearrangement Reaction." Organic Letters 15, no. 20 (2013): 5334–37. http://dx.doi.org/10.1021/ol4025925.

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24

FONG, M. C., and C. H. SCHIESSER. "ChemInform Abstract: Intramolecular Homolytic Substitution with Amidyl Radicals: A Free- Radical Synthesis of Ebselen and Related Analogues." ChemInform 28, no. 37 (2010): no. http://dx.doi.org/10.1002/chin.199737202.

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25

Okamoto, Kazuhiro, Naoki Shida, and Mahito Atobe. "Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process." Beilstein Journal of Organic Chemistry 20 (February 12, 2024): 264–71. http://dx.doi.org/10.3762/bjoc.20.27.

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Electrochemically generated amidyl radical species produced distinct inter- or intramolecular hydroamination reaction products via a proton-coupled electron transfer (PCET) mechanism. Cyclic voltammetry (CV) analysis indicated that the chemoselectivity was derived from the size of the hydrogen bond complex, which consisted of the carbamate substrate and phosphate base, and could be controlled using 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as an additive. These results provide fundamental insights for the design of PCET-based redox reaction systems under electrochemical conditions.

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26

Esker, John L., та Martin Newcomb. "N-Acyl-N-alkylcarbamoyloxy radicals: Entries to amidyl radicals by decar☐ylation and to α-amide radicals by radical translocation". Tetrahedron Letters 33, № 40 (1992): 5913–16. http://dx.doi.org/10.1016/s0040-4039(00)61087-0.

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27

CLARK, A. J., та J. L. PEACOCK. "ChemInform Abstract: An Amidyl Radical Cyclization Approach Towards the Synthesis of β-Lactams." ChemInform 29, № 20 (2010): no. http://dx.doi.org/10.1002/chin.199820121.

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28

Clark, Andrew, David Fullaway, Nicholas Murphy, and Hemal Parekh. "Copper(I) Halide Mediated Tandem 1,4-Aryl Migration-Oxidative Amidyl Radical Cyclisation of Bromosulfonamides." Synlett 2010, no. 04 (2009): 610–14. http://dx.doi.org/10.1055/s-0029-1219151.

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29

Yuan, Xinting, Kun Liu, and Chaozhong Li. "Development of Highly Regioselective Amidyl Radical Cyclization Based on Lone Pair−Lone Pair Repulsion." Journal of Organic Chemistry 73, no. 16 (2008): 6166–71. http://dx.doi.org/10.1021/jo800845b.

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30

Gieshoff, Tile, Anton Kehl, Dieter Schollmeyer, Kevin D. Moeller, and Siegfried R. Waldvogel. "Electrochemical synthesis of benzoxazoles from anilides – a new approach to employ amidyl radical intermediates." Chemical Communications 53, no. 20 (2017): 2974–77. http://dx.doi.org/10.1039/c7cc00927e.

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31

Wu, Kui, Yuliu Du, and Ting Wang. "Visible-Light-Mediated Construction of Pyrroloindolines via an Amidyl Radical Cyclization/Carbon Radical Addition Cascade: Rapid Synthesis of (±)-Flustramide B." Organic Letters 19, no. 20 (2017): 5669–72. http://dx.doi.org/10.1021/acs.orglett.7b02837.

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32

Zheng, Lan, Yu-En Qian, Yuan-Zhuo Hu, et al. "O-Perhalopyridin-4-yl Hydroxylamines: Amidyl-Radical Generation Scaffolds in Photoinduced Direct Amination of Heterocycles." Organic Letters 23, no. 5 (2021): 1643–47. http://dx.doi.org/10.1021/acs.orglett.1c00064.

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33

Artaryan, Alexander, Artur Mardyukov, Kseniya Kulbitski, et al. "Aliphatic C–H Bond Iodination by aN-Iodoamide and Isolation of an ElusiveN-Amidyl Radical." Journal of Organic Chemistry 82, no. 14 (2017): 7093–100. http://dx.doi.org/10.1021/acs.joc.7b00557.

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34

Gryko, Dorota. "(Invited) Application of N-Amino Pyridinium Salts in Photochemical Transformations." ECS Meeting Abstracts MA2025-01, no. 56 (2025): 2717. https://doi.org/10.1149/ma2025-01562717mtgabs.

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Amines play crucial roles as biologically active compounds in medicine, as synthetic intermediates in organic chemistry.1 Along this line, N-amino pyridinium salts have recently received a lot of attention as precursors to generate N-centered radicals via photochemical means.1 These are attractive for generating new C-N bonds, giving access to γ-aminocarbonyl moieties2 or meta-functionalized pyridine.3 Upon light irradiation, electron transfer from the excited state of the Ir(III)*-catalyst to the N-amino pyridinium salt results in the N-N bond cleavage generating an amidyl radical. Subsequent

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35

You, Cai, and Armido Studer. "Three-component 1,2-carboamination of vinyl boronic esters via amidyl radical induced 1,2-migration." Chemical Science 12, no. 47 (2021): 15765–69. http://dx.doi.org/10.1039/d1sc05811h.

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36

Wu, Kui, Lushun Wang, Sonivette Colón‐Rodríguez, Gerd‐Uwe Flechsig, and Ting Wang. "Amidyl Radical Directed Remote Allylation of Unactivated sp 3 C−H Bonds by Organic Photoredox Catalysis." Angewandte Chemie 131, no. 6 (2019): 1788–92. http://dx.doi.org/10.1002/ange.201811004.

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37

Wu, Kui, Lushun Wang, Sonivette Colón‐Rodríguez, Gerd‐Uwe Flechsig, and Ting Wang. "Amidyl Radical Directed Remote Allylation of Unactivated sp 3 C−H Bonds by Organic Photoredox Catalysis." Angewandte Chemie International Edition 58, no. 6 (2019): 1774–78. http://dx.doi.org/10.1002/anie.201811004.

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38

Clark, Andrew J., Robert P. Filik, Gerard H. Thomas, and John Sherringham. "Anti-Beckwith stereoselectivity in amidyl radical cyclisations: Bu3SnH-mediated 5-exo-trig acyl mode cyclisation of 2-substituted pent-4-enamide radicals." Tetrahedron Letters 54, no. 31 (2013): 4094–97. http://dx.doi.org/10.1016/j.tetlet.2013.05.109.

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39

Rey, Valentina, Adriana B. Pierini, and Alicia B. Peñéñory. "Competitive Reaction Pathways foro-Anilide Aryl Radicals: 1,5- or 1,6-Hydrogen Transfer versus Nucleophilic Coupling Reactions. A Novel Rearrangement to Afford an Amidyl Radical." Journal of Organic Chemistry 74, no. 3 (2009): 1223–30. http://dx.doi.org/10.1021/jo801892c.

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40

Biechy, Aurélien, Shuji Hachisu, Béatrice Quiclet-Sire, Louis Ricard, and Samir Z. Zard. "Application of an amidyl radical cascade to the total synthesis of (±)-fortucine leading to the structural revision of kirkine." Tetrahedron 65, no. 33 (2009): 6730–38. http://dx.doi.org/10.1016/j.tet.2009.04.027.

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41

Dekker, E. E. J., J. B. F. N. Engberts, and Th J. de Boer. "Photolysis of some N-cycloalkyl-N-nitrososulfonamides. The interaction between a small cycloalkyl group and an amidyl radical centre." Recueil des Travaux Chimiques des Pays-Bas 96, no. 9 (2010): 230–35. http://dx.doi.org/10.1002/recl.19770960905.

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42

Zhu, Ben-Zhan, Dan Xu, Li Qin, et al. "An unexpected new pathway for nitroxide radical production via more reactve nitrogen-centered amidyl radical intermediate during detoxification of the carcinogenic halogenated quinones by N-alkyl hydroxamic acids." Free Radical Biology and Medicine 146 (January 2020): 150–59. http://dx.doi.org/10.1016/j.freeradbiomed.2019.07.009.

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43

Michon, Josette, Andre Jeunet, Nadia Pelloux, Eric Defrancq, Marie France Lhomme, and Jean Lhomme. "Generation and identification of the amidyl radical resulting from homolytic nitrogous-oxygen cleavage in carcinogenic N-acetyl-N-(acyloxy)-2-aminofluorene." Journal of Organic Chemistry 58, no. 22 (1993): 6143–45. http://dx.doi.org/10.1021/jo00074a054.

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44

Esker, John L., and Martin Newcomb. "Amidyl radicals from N-(phenylthio)amides." Tetrahedron Letters 34, no. 43 (1993): 6877–80. http://dx.doi.org/10.1016/s0040-4039(00)91819-7.

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45

ESKER, J. L., and M. NEWCOMB. "ChemInform Abstract: Amidyl Radicals from N-(Phenylthio)amides." ChemInform 25, no. 17 (2010): no. http://dx.doi.org/10.1002/chin.199417061.

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46

Montevecchi, Pier Carlo, and Maria Luisa Navacchia. "Sulfanyl radical mediated cyclization of aminyl radicals." Tetrahedron Letters 39, no. 49 (1998): 9077–80. http://dx.doi.org/10.1016/s0040-4039(98)01998-4.

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47

Xu, Dan, Chun-Hua Huang, Li Qin, et al. "Corrigendum to “An unexpected new pathway for nitroxide radical production via more reactve nitrogen-centered amidyl radical intermediate during detoxification of the carcinogenic halogenated quinones by N-alkyl hydroxamic acids” [Free Radic. Biol. Med. 146 (2020) 150–159/FRBM_2019_405]." Free Radical Biology and Medicine 152 (May 2020): 869. http://dx.doi.org/10.1016/j.freeradbiomed.2020.03.028.

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48

Foray, Gabriela S., Alicia B. Peñéñory, and Roberto A. Rossi. "Article." Canadian Journal of Chemistry 77, no. 5-6 (1999): 676–80. http://dx.doi.org/10.1139/v99-037.

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The photostimulated reactions of N-cyclopropyl-N-ethyl p-toluensulfonamide (4) with diphenylphosphide ions (2) in liquid ammonia gave 1,3-bis(diphenylphosphinyl)-1-(N-ethyl)propylamine, isolated as the oxide 5, and 1,3-bis(diphenylphosphinyl)-1-propanol, isolated as the oxide 6, all of them corresponding to the aperture of the cyclopropylaminyl radical intermediate. The reaction of 4 with 2 in excess and longer reaction times gave only 5 (73% yield). The photostimulated reactions of N-(n-butyl)-N-cyclobutyl p-toluensulfonamide (13) with 2 in liquid ammonia gave, after oxidation, N-(n-butyl)-N-

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49

Montevecchi, Pier Carlo, and Maria Luisa Navacchia. "ChemInform Abstract: Sulfanyl Radical Mediated Cyclization of Aminyl Radicals." ChemInform 30, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.199909050.

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50

Smith, Peter, та William Harley Donovan. "EPR study of the long-range effect of a β-carbon chiral center on the magnetic equivalence of β-methylene protons". Canadian Journal of Chemistry 66, № 9 (1988): 2304–8. http://dx.doi.org/10.1139/v88-365.

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Using aqueous TiCl3-based continuous-flow, radical-generating methods at 25 °C we have carried out a comprehensive EPR study of hydroxyl- and aminyl-radical addition to eight alkene substrates that yielded radicals of general formula XCH2—ĊY—C*HR1R2, where C* is a chiral center, to investigate the magnetic inequivalence of β-CH2 protons arising from a nonadjacent β-C chiral center. We attribute the observed nonequivalence to the long-range influence of the chiral center in these radicals, and note that our results are consistent with the reasonable expectation that the presence of bulky groups

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