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Journal articles on the topic 'The photochemistry of aryl azides'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Leyva, Elisa, Matthew S. Platz, Silvia E. Loredo-Carrillo, and Johana Aguilar. "Fluoro Aryl Azides: Synthesis, Reactions and Applications." Current Organic Chemistry 24, no. 11 (2020): 1161–80. http://dx.doi.org/10.2174/1385272824999200608132505.

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Background: The complex photochemistry of aryl azides has fascinated scientists for several decades. Spectroscopists have investigated the intermediates formed by different analytical techniques. Theoretical chemists have explained the intrinsic interplay of intermediates under different experimental conditions. Objective & Method: A complete understanding of the photochemistry of a given fluoro aryl azide is a basic requisite for its use in chemistry. In this review, we will discuss the synthesis of several fluoro substituted aryl azides and the reactions and intermediates generated upon

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2

Soto, Juan, Juan C. Otero, Francisco J. Avila, and Daniel Peláez. "Conical intersections and intersystem crossings explain product formation in photochemical reactions of aryl azides." Physical Chemistry Chemical Physics 21, no. 5 (2019): 2389–96. http://dx.doi.org/10.1039/c8cp06974c.

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3

Leyva, Elisa, Daniel Munoz, and Matthew S. Platz. "Photochemistry of fluorinated aryl azides in toluene solution and in frozen polycrystals." Journal of Organic Chemistry 54, no. 25 (1989): 5938–45. http://dx.doi.org/10.1021/jo00286a028.

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4

Schnapp, Karlyn A., Russell Poe, Elisa Leyva, N. Soundararajan, and Matthew S. Platz. "Exploratory photochemistry of fluorinated aryl azides. Implications for the design of photoaffinity labeling reagents." Bioconjugate Chemistry 4, no. 2 (1993): 172–77. http://dx.doi.org/10.1021/bc00020a010.

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5

Morris, Josephine L., Samuel C. Reddington, Damien M. Murphy, D. Dafydd Jones, James A. Platts, and Eric M. Tippmann. "Aryl Azide Photochemistry in Defined Protein Environments." Organic Letters 15, no. 4 (2013): 728–31. http://dx.doi.org/10.1021/ol3028779.

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6

Bucher, Götz, and Hans-Gert Korth. "Photochemistry ofortho-Phenoxymethyl-Substituted Aryl Azides: A Novel Nitrene Rearrangement En Route to Isolable Iminoquinone Methides?" Angewandte Chemie International Edition 38, no. 1-2 (1999): 212–15. http://dx.doi.org/10.1002/(sici)1521-3773(19990115)38:1/2<212::aid-anie212>3.0.co;2-9.

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7

SCHNAPP, K. A., R. POE, E. LEYVA, N. SOUNDARARAJAN, and M. S. PLATZ. "ChemInform Abstract: Exploratory Photochemistry of Fluorinated Aryl Azides. Implications for the Design of Photoaffinity Labeling Reagents." ChemInform 24, no. 30 (2010): no. http://dx.doi.org/10.1002/chin.199330096.

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8

Leyva, Elisa, David H. S. Chang, Matthew S. Platz, David S. Watt, Peter J. Crocker, and Kenji Kawada. "THE PHOTOCHEMISTRY OF IODO, METHYL AND THIOMETHYL SUBSTITUTED ARYL AZIDES IN TOLUENE SOLUTION AND FROZEN POLYCRYSTALS." Photochemistry and Photobiology 54, no. 3 (1991): 329–33. http://dx.doi.org/10.1111/j.1751-1097.1991.tb02024.x.

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9

Burdzinski, Gotard, John C. Hackett, Jin Wang, Terry L. Gustafson, Christopher M. Hadad, and Matthew S. Platz. "Early Events in the Photochemistry of Aryl Azides from Femtosecond UV/Vis Spectroscopy and Quantum Chemical Calculations." Journal of the American Chemical Society 128, no. 41 (2006): 13402–11. http://dx.doi.org/10.1021/ja061520i.

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10

Bucher, Goetz, and Hans-Gert Korth. "ChemInform Abstract: Photochemistry of ortho-Phenoxymethyl-Substituted Aryl Azides: A Novel Nitrene Rearrangement En Route to Isolable Iminoquinone Methides?" ChemInform 30, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199918052.

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11

Sigman, Michael E., Tom Autrey, and Gary B. Schuster. "Aroylnitrenes with singlet ground states: photochemistry of acetyl-substituted aroyl and aryloxycarbonyl azides." Journal of the American Chemical Society 110, no. 13 (1988): 4297–305. http://dx.doi.org/10.1021/ja00221a032.

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12

Shields, Charles J., Douglas R. Chrisope, Gary B. Schuster, Andrew J. Dixon, Martyn Poliakoff, and James J. Turner. "Photochemistry of aryl azides: detection and characterization of a dehydroazepine by time-resolved infrared spectroscopy and flash photolysis at room temperature." Journal of the American Chemical Society 109, no. 15 (1987): 4723–26. http://dx.doi.org/10.1021/ja00249a047.

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13

Li, Zhiquan, Evaldas Stankevičius, Aliasghar Ajami, et al. "3D alkyne–azide cycloaddition: spatiotemporally controlled by combination of aryl azide photochemistry and two-photon grafting." Chemical Communications 49, no. 69 (2013): 7635. http://dx.doi.org/10.1039/c3cc43533d.

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14

Ren, Daniel, and Robert A. McClelland. "Carbocation-like reactivity patterns in X'-substituted-4-biphenylylnitrenium ions." Canadian Journal of Chemistry 76, no. 1 (1998): 78–84. http://dx.doi.org/10.1139/v97-204.

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4-Azido-X'-substituted biphenyls (X' = 4'-MeO, 4'-Me, 4'-F, 3'-Me, 4'-Cl, H, 3'-MeO, 3'-Cl, 4'-CF3) have been prepared and subjected to 248 nm flash photolysis irradiation in 20:80 acetonitrile:water. Transient X'-substituted 4-biphenylylnitrenium ions 10 (Ar C6H4-N + H) are observed, with lifetimes ranging from 0.6 ms (4'-MeO) to 26 ns (4'-CF3). These cations are quenched by azide ion, with values of kaz ranging from 6 to 10 x 109 M-1 s-1, with the majority in the range (9-10) x 109. This near constant kaz provides further evidence that arylnitrenium ions are quenched by azide ion at the diff

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15

Wollman, Eric W., Doris Kang, C. Daniel Frisbie, Ivan M. Lorkovic, and Mark S. Wrighton. "Photosensitive Self-Assembled Monolayers on Gold: Photochemistry of Surface-Confined Aryl Azide and Cyclopentadienylmanganese Tricarbonyl." Journal of the American Chemical Society 116, no. 10 (1994): 4395–404. http://dx.doi.org/10.1021/ja00089a030.

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16

Melvin, T., and Gary B. Schuster. "THE PHOTOCHEMISTRY OF ACETYL-SUBSTITUTED AROYL AZIDES: THE DESIGN OF PHOTOLABELING AGENTS FOR INERT SITES IN HYDROPHOBIC REGIONS." Photochemistry and Photobiology 51, no. 2 (1990): 155–60. http://dx.doi.org/10.1111/j.1751-1097.1990.tb01697.x.

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17

Burdzinski, Gotard T., Terry L. Gustafson, John C. Hackett, Christopher M. Hadad, and Matthew S. Platz. "The Direct Detection of an Aryl Azide Excited State: An Ultrafast Study of the Photochemistry ofpara- andortho-Biphenyl Azide." Journal of the American Chemical Society 127, no. 40 (2005): 13764–65. http://dx.doi.org/10.1021/ja054135m.

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18

Watt, David S., Kenji Kawada, Elisa Leyva, and Matthew S. Platz. "Exploratory photochemistry of iodinated aromatic azides." Tetrahedron Letters 30, no. 8 (1989): 899–902. http://dx.doi.org/10.1016/s0040-4039(00)95273-0.

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19

Budyka, M. F. "Photochemistry of aromatic azides and nitrenes." High Energy Chemistry 41, no. 3 (2007): 176–87. http://dx.doi.org/10.1134/s0018143907030058.

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20

Kuhn, Arvid, and Wolfram Sander. "Photochemistry of Matrix-Isolated Phenylsilyl Azides." Organometallics 17, no. 22 (1998): 4776–83. http://dx.doi.org/10.1021/om9801296.

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21

Leyva, Elisa, Ruben Sagredo, and Edgar Moctezuma. "Photochemistry of fluorophenyl azides in aniline." Journal of Fluorine Chemistry 125, no. 5 (2004): 741–47. http://dx.doi.org/10.1016/j.jfluchem.2003.12.011.

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22

Nielsen, Peter E., and Ole Buchardt. "ARYL AZIDES AS PHOTOAFFINITY LABELS. A PHOTOCHEMICAL STUDY OF SOME 4-SUBSTITUTED ARYL AZIDES." Photochemistry and Photobiology 35, no. 3 (2008): 317–23. http://dx.doi.org/10.1111/j.1751-1097.1982.tb02568.x.

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23

Tsao, Meng-Lin, and Matthew S. Platz. "Photochemistry of Ortho, Ortho‘ Dialkyl Phenyl Azides." Journal of the American Chemical Society 125, no. 39 (2003): 12014–25. http://dx.doi.org/10.1021/ja035833e.

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24

Kim, Yongjin, Young Ho Rhee, and Jaiwook Park. "Redox reaction between benzyl azides and aryl azides: concerted synthesis of aryl nitriles and anilines." Organic & Biomolecular Chemistry 15, no. 7 (2017): 1636–41. http://dx.doi.org/10.1039/c6ob02615j.

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25

Wakasa, Masanobu, Isao Yoneda, and Kunio Mochida. "Photochemistry of aryl-substituted trigermanes." Journal of Organometallic Chemistry 366, no. 1-2 (1989): C1—C5. http://dx.doi.org/10.1016/0022-328x(89)87334-6.

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26

Nomura, Mitsushiro, Asuka Kawakita, Hideaki Katsuta, et al. "Reactions of cobaltadithiolene complexes with aryl azides." Journal of Organometallic Chemistry 681, no. 1-2 (2003): 180–88. http://dx.doi.org/10.1016/s0022-328x(03)00599-0.

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27

Garanti, Luisa, Giorgio Molteni, and Gianluigi Broggini. "Intramolecular cycloadditions of N-alkenoyl aryl azides." Journal of the Chemical Society, Perkin Transactions 1, no. 15 (2001): 1816–19. http://dx.doi.org/10.1039/b102686k.

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28

Veiko, N. N., A. V. Karpukhin, A. G. Salimov, and D. N. Spitkovskii. "Modification of DNA by photoactivable aryl azides." Chemistry of Natural Compounds 25, no. 2 (1989): 224–28. http://dx.doi.org/10.1007/bf00598417.

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29

Budyka, Mikhayl F. "ChemInform Abstract: Photochemistry of Azidopyridine and Related Heterocyclic Azides." ChemInform 42, no. 27 (2011): no. http://dx.doi.org/10.1002/chin.201127214.

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30

Jin, Hui, Zhen Dong Huang, Chun Xiang Kuang, and Xiao Kun Wang. "Iron-catalyzed bromination of aryl azides by N-bromosuccinimide: Efficient method for the synthesis of brominated aryl azides." Chinese Chemical Letters 22, no. 3 (2011): 310–13. http://dx.doi.org/10.1016/j.cclet.2010.10.024.

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31

Liang, Xifu, Jacob Andersen, Ulf Madsen, and Fredrik Björkling. "Rapid Synthesis of Aryl Azides from Aryl Halides under Mild Conditions." Synlett, no. 14 (2005): 2209–13. http://dx.doi.org/10.1055/s-2005-872248.

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32

Xie, Sheng, Yang Zhang, Olof Ramström, and Mingdi Yan. "Base-catalyzed synthesis of aryl amides from aryl azides and aldehydes." Chemical Science 7, no. 1 (2016): 713–18. http://dx.doi.org/10.1039/c5sc03510d.

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33

Wang, Teng, Hang Yin, and Ning Jiao. "Copper-Catalyzed Oxidative Transformation of Aryl Propargylic Azides to Aryl Propiolonitriles." Advanced Synthesis & Catalysis 355, no. 6 (2013): 1207–10. http://dx.doi.org/10.1002/adsc.201201056.

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34

Godoy Prieto, Leonela, Marcos J. Lo Fiego, Alicia B. Chopa, and María T. Lockhart. "A reliable one-pot synthesis of aryl azides from aryl amines using organotin azides as effective and recoverable reagents." Journal of Organometallic Chemistry 830 (February 2017): 26–32. http://dx.doi.org/10.1016/j.jorganchem.2016.11.037.

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35

HAN, K., and G. HE. "Photochemistry of aryl halides: Photodissociation dynamics." Journal of Photochemistry and Photobiology C: Photochemistry Reviews 8, no. 2 (2007): 55–66. http://dx.doi.org/10.1016/j.jphotochemrev.2007.03.002.

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36

Geiger, U., and Y. Haas. "Photochemistry of Aryl Pentazoles: para-Methoxyphenylpentazole." Journal of Physical Chemistry B 119, no. 24 (2015): 7338–48. http://dx.doi.org/10.1021/jp5108813.

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37

Lemir, Ignacio D., Juan E. Argüello, Anabel E. Lanterna, and Juan C. Scaiano. "Heterogeneous photocatalysis of azides: extending nitrene photochemistry to longer wavelengths." Chemical Communications 56, no. 70 (2020): 10239–42. http://dx.doi.org/10.1039/d0cc04118a.

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38

Hajipour, Abdol R., and Fatemeh Mohammadsaleh. "Synthesis of aryl azides from aryl halides promoted by Cu2O/tetraethylammonium prolinate." Tetrahedron Letters 55, no. 50 (2014): 6799–802. http://dx.doi.org/10.1016/j.tetlet.2014.10.045.

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39

Zeng, Ming, Yu Hua Yang, Jin Jing Li, Ying Chen, Dong Mei Cui, and Chen Zhang. "Copper Catalyzed Synthesis of Aryl Azides from Aryl Bromides and Sodium Azide." Asian Journal of Chemistry 27, no. 5 (2015): 1698–700. http://dx.doi.org/10.14233/ajchem.2015.17551.

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40

Konev, Mikhail O., T. Andrew McTeague, and Jeffrey W. Johannes. "Nickel-Catalyzed Photoredox-Mediated Cross-Coupling of Aryl Electrophiles and Aryl Azides." ACS Catalysis 8, no. 10 (2018): 9120–24. http://dx.doi.org/10.1021/acscatal.8b02954.

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41

Das, Jagattaran, Santoshkumar N. Patil, Riti Awasthi, C. Prasad Narasimhulu, and Sanjay Trehan. "An Easy Access to Aryl Azides from Aryl Amines under Neutral Conditions." Synthesis 2005, no. 11 (2005): 1801–6. http://dx.doi.org/10.1055/s-2005-869974.

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42

Budruev, A. V., and D. Yu Sinjagina. "Photochemical modification of polyethylene surface with aryl azides." High Energy Chemistry 47, no. 5 (2013): 237–41. http://dx.doi.org/10.1134/s0018143913050020.

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43

Crocker, Peter J., Nobuyuki Imai, Krishnan Rajagopalan, et al. "Heterobifunctional cross-linking agents incorporating perfluorinated aryl azides." Bioconjugate Chemistry 1, no. 6 (1990): 419–24. http://dx.doi.org/10.1021/bc00006a008.

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44

Katsuta, Hideaki, Naoko Noguchi, Yohsuke Inomata, Masatsugu Kajitani, Takeo Akiyama, and Akira Sugimori. "Reactions of Aryl Azides with Cobaltadithiolenes. Substitution ReactionsviaNitrene." Chemistry Letters 23, no. 7 (1994): 1165–68. http://dx.doi.org/10.1246/cl.1994.1165.

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45

Wei, Kaijie, Tonghao Yang, Qing Chen, Siyu Liang, and Wei Yu. "Iron-catalysed 1,2-aryl migration of tertiary azides." Chemical Communications 56, no. 78 (2020): 11685–88. http://dx.doi.org/10.1039/d0cc04579a.

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46

Rasmussen, Lars Kyhn, Brant C. Boren, and Valery V. Fokin. "Ruthenium-Catalyzed Cycloaddition of Aryl Azides and Alkynes." Organic Letters 9, no. 26 (2007): 5337–39. http://dx.doi.org/10.1021/ol701912s.

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47

Budyka, M. F., M. M. Kantor, and R. M. Fatkulbayanov. "Effect of diphenylamine on photodissociation of aryl azides." Russian Chemical Bulletin 46, no. 2 (1997): 265–68. http://dx.doi.org/10.1007/bf02494359.

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48

Jin, Hui, Zhen Dong Huang, Chun Xiang Kuang, and Xiao Kun Wang. "ChemInform Abstract: Iron-Catalyzed Bromination of Aryl Azides by N-Bromosuccinimide: Efficient Method for the Synthesis of Brominated Aryl Azides." ChemInform 42, no. 20 (2011): no. http://dx.doi.org/10.1002/chin.201120077.

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49

Hassan, Hani Mutlak A. "A Highly Efficient Ga(OTf)3/KI-Catalysed Transformation of aryl azides to aryl amines using low catalyst loading." Journal of Chemical Research 42, no. 11 (2018): 572–74. http://dx.doi.org/10.3184/174751918x15404076150031.

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50

Hajipour, Abdol, Morteza Karimzadeh, and Sirous Ghorbani. "Selective Azidation of Aryl Halides to Aryl Azides Promoted by Proline and CuFeO2." Synlett 25, no. 20 (2014): 2903–7. http://dx.doi.org/10.1055/s-0034-1378903.

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