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Journal articles on the topic 'Nitrenen'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Wentrup, Curt, and David Kvaskoff. "1,5-(1,7)-Biradicals and Nitrenes Formed by Ring Opening of Hetarylnitrenes." Australian Journal of Chemistry 66, no. 3 (2013): 286. http://dx.doi.org/10.1071/ch12502.

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Several aromatic and heteroaromatic nitrenes and carbenes undergo photochemical and sometimes also thermal ring opening. Depending on benz-annelation, the ring-opened species may have the character of either nitrenes (for α-annelation) or 1,5-(1,7-)-biradicals (for β-annelation). Both types have been observed, and they are clearly distinguished by their characteristic electron spin resonance spectra. In addition, ring opening of hetarylnitrenes to nitrile ylides can be observed whenever there is a meta-relationship between a ring nitrogen atom and the nitrene (or carbene) centre. The factors g

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2

Badiei, Yosra M., Ammani Krishnaswamy, Marie M. Melzer, and Timothy H. Warren. "Transient Terminal Cu−Nitrene Intermediates from Discrete Dicopper Nitrenes." Journal of the American Chemical Society 128, no. 47 (2006): 15056–57. http://dx.doi.org/10.1021/ja065299l.

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3

Chapyshev, Sergei V., Denis V. Korchagin, Patrik Neuhaus, and Wolfram Sander. "High-spin intermediates of the photolysis of 2,4,6-triazido-3-chloro-5-fluoropyridine." Beilstein Journal of Organic Chemistry 9 (April 16, 2013): 733–42. http://dx.doi.org/10.3762/bjoc.9.83.

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In contrast to theoretical expectations, the photolysis of 2,4,6-triazido-3-chloro-5-fluoropyridine in argon at 5 K gives rise to EPR peaks of just two triplet mononitrenes, two quintet dinitrenes, and a septet trinitrene. EPR spectral simulations in combination with DFT calculations show that observable nitrenes can be assigned to triplet 2,4-diazido-3-chloro-5-fluoropyridyl-6-nitrene (D T = 1.026 cm−1, E T = 0), triplet 2,6-diazido-3-chloro-5-fluoropyridyl-4-nitrene (D T = 1.122 cm−1, E T = 0.0018 cm−1), quintet 4-azido-3-chloro-5-fluoropyridyl-2,6-dinitrene (D Q = 0.215 cm−1, E Q = 0.0545 c

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4

Chapyshev, Sergei V. "Zero-field splitting parameters of triplet nitreno-s-triazines: a new insight into the geometry of the nitrene centres of triplet and singlet nitrenes." Mendeleev Communications 12, no. 6 (2002): 227–29. http://dx.doi.org/10.1070/mc2002v012n06abeh001683.

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5

Schomaker, Jennifer M., Logan E. Vine, and Emily E. Zerull. "Taming Nitrene Reactivity with Silver Catalysts." Synlett 32, no. 01 (2020): 30–44. http://dx.doi.org/10.1055/s-0040-1707197.

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Nitrene transfer (NT) is a convenient strategy to directly transform C–H bonds into more valuable C–N bonds and exciting advances have been made to improve selectivity. Our work in silver-based NT has shown the unique ability of this metal to enable tunable chemo-, site-, and stereoselective reactions using simple N-dentate ligand scaffolds. Manipulation of the coordination environment and noncovalent interactions around the silver center furnish unprecedented catalyst control in selective NT and provide insights for further improvements in the field.1 Introduction1.1 Strategies for Nitrene Tr

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6

Schock, Marvin, and Stefan Bräse. "Reactive & Efficient: Organic Azides as Cross-Linkers in Material Sciences." Molecules 25, no. 4 (2020): 1009. http://dx.doi.org/10.3390/molecules25041009.

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The exceptional reactivity of the azide group makes organic azides a highly versatile family of compounds in chemistry and the material sciences. One of the most prominent reactions employing organic azides is the regioselective copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition with alkynes yielding 1,2,3-triazoles. Other named reactions include the Staudinger reduction, the aza-Wittig reaction, and the Curtius rearrangement. The popularity of organic azides in material sciences is mostly based on their propensity to release nitrogen by thermal activation or photolysis. On the one hand, th

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7

Ozturk, Turan, and Alexander McKillop. "The synthesis of pyrido(2,3,4-kl)acridine unit of some marine alkaloids." Canadian Journal of Chemistry 78, no. 9 (2000): 1158–64. http://dx.doi.org/10.1139/v00-119.

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A simple and convenient synthesis of pyrido(2,3,4-kl)acridine (1), the main skeleton of some marine alkaloids, via cyclization and intramolecular nitrene insertion, is described. The importance of the planarity of the molecule during the nitrene insertion is explained.Key words: pyridoacridine, marine alkaloids, nitrene insertion, quinoline, quinolinone.

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8

Carsch, Kurtis M., Ida M. DiMucci, Diana A. Iovan, et al. "Synthesis of a copper-supported triplet nitrene complex pertinent to copper-catalyzed amination." Science 365, no. 6458 (2019): 1138–43. http://dx.doi.org/10.1126/science.aax4423.

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Terminal copper-nitrenoid complexes have inspired interest in their fundamental bonding structures as well as their putative intermediacy in catalytic nitrene-transfer reactions. Here, we report that aryl azides react with a copper(I) dinitrogen complex bearing a sterically encumbered dipyrrin ligand to produce terminal copper nitrene complexes with near-linear, short copper–nitrenoid bonds [1.745(2) to 1.759(2) angstroms]. X-ray absorption spectroscopy and quantum chemistry calculations reveal a predominantly triplet nitrene adduct bound to copper(I), as opposed to copper(II) or copper(III) a

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9

de Bruin, Bas, and Colet te Grotenhuis. "Radical-type Reactions Controlled by Cobalt: From Carbene Radical Reactivity to the Catalytic Intermediacy of Reactive o-Quinodimethanes." Synlett 29, no. 17 (2018): 2238–50. http://dx.doi.org/10.1055/s-0037-1610204.

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In this account, we summarize our recent efforts in the fields of ‘open-shell organometallic chemistry’ and ‘metalloradical catalysis’. We focus in particular on the use of so-called ‘carbene radicals’ for the synthesis of a variety of useful synthons for organic chemistry. We further show that unexpected reactivity arises from catalytic synthesis of unusual o-quinone methide and o-quinodimethane intermediates that undergo subsequent rearrangements to uncommon products.1 Introduction2 General (Fischer-Type) Carbene and Nitrene Reactivity and Their Relation to Carbene and Nitrene Radical Reacti

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10

Scamp, Ryan J., Bradley Scheffer, and Jennifer M. Schomaker. "Regioselective differentiation of vicinal methylene C–H bonds enabled by silver-catalysed nitrene transfer." Chemical Communications 55, no. 51 (2019): 7362–65. http://dx.doi.org/10.1039/c9cc04006d.

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11

Liu, Jin-Biao, Miaofeng Ren, Xiaojing Lai, and Guanyinsheng Qiu. "Iron-catalyzed stereoselective haloamidation of amide-tethered alkynes." Chemical Communications 57, no. 35 (2021): 4259–62. http://dx.doi.org/10.1039/d1cc00870f.

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In this work, by using N-methoxybenzamides as efficient acyl nitrene precursors, an iron-catalyzed acyl nitrene/alkyne metalation-based chloramidation is reported for the synthesis of isoindol-5-ones.

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12

Lai, Xiaojing, Jin-Biao Liu, Yu-Chao Wang, and Guanyinsheng Qiu. "Iron-catalyzed intramolecular acyl nitrene/alkyne metalation for the synthesis of pyrrolo[2,1-a]isoindol-5-ones." Chemical Communications 57, no. 16 (2021): 2077–80. http://dx.doi.org/10.1039/d0cc08039j.

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13

Wang, Haiyu, Yuxi Li, Zhiming Wang, et al. "Iron-catalyzed efficient intermolecular amination of C(sp3)–H bonds with bromamine-T as nitrene source." RSC Adv. 4, no. 48 (2014): 25287–90. http://dx.doi.org/10.1039/c4ra02240h.

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[Fe(N4Py)(CH<sub>3</sub>CN)](ClO<sub>4</sub>)<sub>2</sub> can efficiently catalyze intermolecular nitrene insertion of sp<sup>3</sup> C–H bonds with bromamine-T as the nitrene source, forming the desired tosylprotected amines with NaBr as the by-product.

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14

Panov, Maxim S., Valentyna D. Voskresenska, Mikhail N. Ryazantsev, Alexander N. Tarnovsky, and R. Marshall Wilson. "5-Azido-2-aminopyridine, a New Nitrene/Nitrenium Ion Photoaffinity Labeling Agent That Exhibits Reversible Intersystem Crossing between Singlet and Triplet Nitrenes." Journal of the American Chemical Society 135, no. 51 (2013): 19167–79. http://dx.doi.org/10.1021/ja405637b.

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15

Li, Jian, Meng-Kai Liu, Quan-Song Li, and Ze-Sheng Li. "Theoretical study on the photochemistry of furoylazides: Curtius rearrangement and subsequent reactions." Physical Chemistry Chemical Physics 22, no. 48 (2020): 28317–24. http://dx.doi.org/10.1039/d0cp05539e.

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16

Feng, Tao, Zhihui Tang, Xiaoli Luo, and Junming Mo. "An efficient imidation of thioethers with nitrene in water." Organic & Biomolecular Chemistry 18, no. 33 (2020): 6497–501. http://dx.doi.org/10.1039/d0ob01539c.

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17

Abram, Sarah-Luise, Inés Monte-Pérez, Florian Felix Pfaff, Erik R. Farquhar, and Kallol Ray. "Evidence of two-state reactivity in alkane hydroxylation by Lewis-acid bound copper–nitrene complexes." Chem. Commun. 50, no. 69 (2014): 9852–54. http://dx.doi.org/10.1039/c4cc03754e.

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18

Fujita, Daiki, Hideki Sugimoto, Yoshihito Shiota, Yuma Morimoto, Kazunari Yoshizawa, and Shinobu Itoh. "Catalytic C–H amination driven by intramolecular ligand-to-nitrene one-electron transfer through a rhodium(iii) centre." Chemical Communications 53, no. 35 (2017): 4849–52. http://dx.doi.org/10.1039/c7cc01840a.

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19

Wang, Yu-Chao, Xiao-Jing Lai, Keke Huang, et al. "Unravelling nitrene chemistry from acyclic precursors: recent advances and challenges." Organic Chemistry Frontiers 8, no. 7 (2021): 1677–93. http://dx.doi.org/10.1039/d0qo01360a.

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20

Takayama, Terufumi, Takahiro Mitsumori, Masaki Kawano, et al. "Direct observation of arylnitrene formation in the photoreaction of arylazide crystals." Acta Crystallographica Section B Structural Science 66, no. 6 (2010): 639–46. http://dx.doi.org/10.1107/s0108768110036608.

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Seven crystal structures of arylazides, 2-azidobiphenyl (2), 4-(4-azidophenyl)butanoic acid (3), 3-azidobenzoic acid (4), N-(4-azidophenyl)acetamide (5), 2,4,6-trichlorophenyl azide (6), 2,5-dibromophenyl azide (7) and 2,4,6-tribromophenyl azide (8), have been analyzed by X-rays. When the crystals were irradiated with UV light at ≃ 80 K, only 2-azidobiphenyl gradually changed its cell dimensions with the retention of the single-crystal form. The crystal structure after photo-irradiation was analyzed by X-rays under the same conditions as those before photo-irradiation. Approximately 20% of the

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21

Peng, Xing-Liang, Wei-Lu Ding, Quan-Song Li, and Ze-Sheng Li. "Theoretical insights into photo-induced Curtius rearrangement of chlorodifluoroacetyl azide." Organic Chemistry Frontiers 4, no. 6 (2017): 1153–61. http://dx.doi.org/10.1039/c7qo00083a.

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22

Willenbockel, Martin, Reinhard J. Maurer, Christopher Bronner, et al. "Coverage-driven dissociation of azobenzene on Cu(111): a route towards defined surface functionalization." Chemical Communications 51, no. 83 (2015): 15324–27. http://dx.doi.org/10.1039/c5cc05003k.

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23

Heins, Spencer P., Peter T. Wolczanski, Thomas R. Cundari, and Samantha N. MacMillan. "Redox non-innocence permits catalytic nitrene carbonylation by (dadi)TiNAd (Ad = adamantyl)." Chemical Science 8, no. 5 (2017): 3410–18. http://dx.doi.org/10.1039/c6sc05610e.

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24

Fauché, Kévin, Lionel Nauton, Laurent Jouffret, Federico Cisnetti, and Arnaud Gautier. "A catalytic intramolecular nitrene insertion into a copper(i)–N-heterocyclic carbene bond yielding fused nitrogen heterocycles." Chemical Communications 53, no. 15 (2017): 2402–5. http://dx.doi.org/10.1039/c6cc09160a.

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25

Yang, Yang, Xianxu Chu, Yan Lu, Manabu Abe, and Xiaoqing Zeng. "Chloro- and Dichloro-methylsulfonyl Nitrenes: Spectroscopic Characterization, Photoisomerization, and Thermal Decomposition." Molecules 23, no. 12 (2018): 3312. http://dx.doi.org/10.3390/molecules23123312.

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Chloro- and dichloro-methylsulfonyl nitrenes, CH2ClS(O)2N and CHCl2S(O)2N, have been generated from UV laser photolysis (193 and 266 nm) of the corresponding sulfonyl azides CH2ClS(O)2N3 and CHCl2S(O)2N3, respectively. Both nitrenes have been characterized with matrix-isolation IR and EPR spectroscopy in solid N2 (10 K) and glassy toluene (5 K) matrices. Triplet ground-state multiplicity of CH2ClS(O)2N (|D/hc| = 1.57 cm−1 and |E/hc| = 0.0026 cm−1) and CHCl2S(O)2N (|D/hc| = 1.56 cm−1 and |E/hc| = 0.0042 cm−1) has been confirmed. In addition, dichloromethylnitrene CHCl2N (|D/hc| = 1.57 cm−1 and

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26

Kang, Jian, Baofu Zhu, Jiewei Liu, Bo Wang, Li Zhang, and Cheng-Yong Su. "Chiral dirhodium catalysts derived from l-serine, l-threonine and l-cysteine: design, synthesis and application." Organic Chemistry Frontiers 2, no. 8 (2015): 890–907. http://dx.doi.org/10.1039/c5qo00110b.

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27

Shukla, Prashant, Suhasini Mahata, Anjumala Sahu, Manorama Singh, Vijai K. Rai, and Ankita Rai. "First graphene oxide promoted metal-free nitrene insertion into olefins in water: towards facile synthesis of activated aziridines." RSC Adv. 7, no. 77 (2017): 48723–29. http://dx.doi.org/10.1039/c7ra09351a.

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28

Rodrigues, Romain, Yanis Lazib, Julien Maury, et al. "Approach to pactamycin analogues using rhodium(ii)-catalyzed alkene aziridination and C(sp3)–H amination reactions." Organic Chemistry Frontiers 5, no. 6 (2018): 948–53. http://dx.doi.org/10.1039/c7qo00878c.

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29

Beiranvand, Z., A. Kakanejadifard, I. S. Donskyi, et al. "Functionalization of fullerene at room temperature: toward new carbon vectors with improved physicochemical properties." RSC Advances 6, no. 114 (2016): 112771–75. http://dx.doi.org/10.1039/c6ra23419d.

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30

Kulkarni, Anand M., Kolluru Srinivas, Mukund V. Deshpande, and Chepuri V. Ramana. "Cu-catalyzed sequential C–N bond formations: expeditious synthesis of tetracyclic indoloindol-3-ones." Organic Chemistry Frontiers 3, no. 1 (2016): 43–46. http://dx.doi.org/10.1039/c5qo00248f.

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31

Ito, Motoki, Arisa Tanaka, Keiju Hatakeyama, Emi Kano, Kazuhiro Higuchi, and Shigeo Sugiyama. "One-pot generation of benzynes from 2-aminophenylboronates via a Rh(ii)-catalyzed N–H amination/oxidation/elimination cascade process." Organic Chemistry Frontiers 7, no. 1 (2020): 64–68. http://dx.doi.org/10.1039/c9qo01115c.

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32

Lehr, Joshua, Manuel Tropiano, Paul D. Beer, Stephen Faulkner, and Jason J. Davis. "Reversible redox modulation of a lanthanide emissive molecular film." Chemical Communications 51, no. 30 (2015): 6515–17. http://dx.doi.org/10.1039/c5cc01097g.

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33

Corbin, Joshua R., and Jennifer M. Schomaker. "Tunable differentiation of tertiary C–H bonds in intramolecular transition metal-catalyzed nitrene transfer reactions." Chemical Communications 53, no. 31 (2017): 4346–49. http://dx.doi.org/10.1039/c7cc01235g.

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34

Cockman, R. W., and R. D. Peacock. "The nitrene OsF5(NCl)." Journal of Fluorine Chemistry 30, no. 4 (1986): 469–70. http://dx.doi.org/10.1016/s0022-1139(00)85101-5.

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35

Kang, Xiongwu, Yang Song, and Shaowei Chen. "Nitrene-functionalized ruthenium nanoparticles." Journal of Materials Chemistry 22, no. 36 (2012): 19250. http://dx.doi.org/10.1039/c2jm33783e.

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36

Yeston, Jake. "Catching a copper nitrene." Science 365, no. 6458 (2019): 1131.4–1132. http://dx.doi.org/10.1126/science.365.6458.1131-d.

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37

Zhang, Guang-Yi, Yi Peng, Jing Xue, Yan-Hui Fan, and Qing-Hai Deng. "Copper-catalyzed nitrene transfer/cyclization cascade to synthesize 3a-nitrogenous furoindolines and pyrroloindolines." Organic Chemistry Frontiers 6, no. 24 (2019): 3934–38. http://dx.doi.org/10.1039/c9qo01124b.

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38

Dong, Yuyang, James T. Lukens, Ryan M. Clarke, Shao-Liang Zheng, Kyle M. Lancaster, and Theodore A. Betley. "Synthesis, characterization and C–H amination reactivity of nickel iminyl complexes." Chemical Science 11, no. 5 (2020): 1260–68. http://dx.doi.org/10.1039/c9sc04879k.

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39

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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40

So, Jongho, Seji Kim, Kyung-Bin Cho, and Yunho Lee. "Metal–ligand cooperative transformation of alkyl azide to isocyanate occurring at a Co–Si moiety." Chemical Communications 57, no. 26 (2021): 3219–22. http://dx.doi.org/10.1039/d0cc08012h.

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41

Kriegel, Benjamin M., Robert G. Bergman, and John Arnold. "Nitrene Metathesis and Catalytic Nitrene Transfer Promoted by Niobium Bis(imido) Complexes." Journal of the American Chemical Society 138, no. 1 (2015): 52–55. http://dx.doi.org/10.1021/jacs.5b11287.

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42

Pearce, Adam J., Xin Yi See, and Ian A. Tonks. "Oxidative nitrene transfer from azides to alkynes via Ti(ii)/Ti(iv) redox catalysis: formal [2+2+1] synthesis of pyrroles." Chemical Communications 54, no. 50 (2018): 6891–94. http://dx.doi.org/10.1039/c8cc02623h.

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43

Coin, Guillaume, Patrick Dubourdeaux, Pierre-Alain Bayle, Colette Lebrun, Pascale Maldivi, and Jean-Marc Latour. "Imidazoline synthesis: mechanistic investigations show that Fe catalysts promote a new multicomponent redox reaction." Dalton Transactions 50, no. 19 (2021): 6512–19. http://dx.doi.org/10.1039/d1dt00919b.

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Integrated experimental and computational studies reveal a new mechanism for Fe-catalyzed imidazoline synthesis through combined nitrene transfer and acetonitrile attack of a styrenyl radical intermediate.

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44

Pan, Chongqing, Si-Yong Yin, Qing Gu, and Shu-Li You. "CpxM(iii)-catalyzed enantioselective C–H functionalization through migratory insertion of metal–carbenes/nitrenes." Organic & Biomolecular Chemistry 19, no. 34 (2021): 7264–75. http://dx.doi.org/10.1039/d1ob01248g.

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In this review, we highlight the developments in chiral CpxM(iii) complexes or achiral CpxM(iii) complexes/chiral carboxylic acid-catalyzed enantioselective C–H functionalization reactions through migratory insertion of metal–carbenes/nitrenes.

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45

Kurup, Sudheer S., Duleeka Wannipurage, Richard L. Lord, and Stanislav Groysman. "Tying the alkoxides together: an iron complex of a new chelating bulky bis(alkoxide) demonstrates selectivity for coupling of non-bulky aryl nitrenes." Chemical Communications 55, no. 72 (2019): 10780–83. http://dx.doi.org/10.1039/c9cc05319k.

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46

Wan, Huabin, Hongmin Li, Jian Xu, et al. "N-Methylcarbamoyl azide: spectroscopy, X-ray structure and decomposition via methylcarbamoyl nitrene." Organic Chemistry Frontiers 4, no. 9 (2017): 1839–48. http://dx.doi.org/10.1039/c7qo00277g.

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47

Hou, Kaipeng, David A. Hrovat, and Xiaoguang Bao. "Computational exploration of the mechanism of copper-catalyzed aromatic C–H bond amination of benzene via a nitrene insertion approach." Chemical Communications 51, no. 84 (2015): 15414–17. http://dx.doi.org/10.1039/c5cc06064h.

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48

Egger, Julian, and Erick M. Carreira. "Efficient synthesis strategies by application of transition metal-catalyzed carbene/nitrene insertions into C–H bonds." Nat. Prod. Rep. 31, no. 4 (2014): 449–55. http://dx.doi.org/10.1039/c3np70084d.

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This Highlight article provides an overview of recent total syntheses that are characterized by high efficiency and enabled through a neat application of transition metal-catalyzed insertions of carbenes and nitrenes into C–H bonds.

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49

Song, Dan, Changfeng Huang, Peishi Liang, Baofu Zhu, Xiang Liu, and Hua Cao. "Lewis acid-catalyzed regioselective C–H carboxamidation of indolizines with dioxazolones via an acyl nitrene type rearrangement." Organic Chemistry Frontiers 8, no. 11 (2021): 2583–88. http://dx.doi.org/10.1039/d1qo00224d.

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An efficient, direct, and novel Lewis acid-catalyzed regioselective C–H carboxamidation of indolizines with dioxazolones via an acyl nitrene type rearrangement under metal-free conditions has been documented.

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50

Zardi, Paolo, Daniela Intrieri, Daniela Maria Carminati, Francesco Ferretti, Piero Macchi та Emma Gallo. "Synthesis and catalytic activity of μ-oxo ruthenium(IV) porphyrin species to promote amination reactions". Journal of Porphyrins and Phthalocyanines 20, № 08n11 (2016): 1156–65. http://dx.doi.org/10.1142/s1088424616500814.

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This work describes the synthesis of ruthenium(IV) [Formula: see text]-oxo porphyrin complexes of general formula [RuIV(TPP)(X)]2O which have been applied as catalysts in nitrene transfer reactions using aryl azides (ArN[Formula: see text] as nitrene sources. Collected data indicated that the catalytic efficiency of [RuIV(TPP)(OCH[Formula: see text]]2O was comparable to that of RuII(TPP)CO because of their analogous reactivity towards aryl azides to give the same catalytically active bis-imido species RuVI(TPP)(ArN)2. The reaction of [RuIV(TPP)(OCH[Formula: see text]]2O with Ph3CN3 or (CH[Form

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