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Journal articles on the topic 'Diazo-transfer'

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Published: 14 March 2023

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1

Russo, Laura, Stefano Zanini, Claudia Riccardi, Francesco Nicotra, and Laura Cipolla. "Diazo transfer for azido-functional surfaces." Materials Today 14, no. 4 (April 2011): 164–69. http://dx.doi.org/10.1016/s1369-7021(11)70088-8.

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2

Ghosh, Somnath, and Indira Datta. "Diazo Transfer Reaction in Solid State." Synthetic Communications 21, no. 2 (January 1991): 191–200. http://dx.doi.org/10.1080/00397919108020811.

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3

Villalgordo, Jos� M., Adelheid Enderli, Anthony Linden, and Heinz Heimgartner. "Diazo-Transfer Reaction with Diphenyl Phosphorazidate." Helvetica Chimica Acta 78, no. 8 (December 13, 1995): 1983–98. http://dx.doi.org/10.1002/hlca.19950780807.

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4

Jászay, Zsuzsa M., Truong Son Pham, Katalin Gönczi, Imre Petneházy, and László Tőke. "Efficient Solid/Liquid Phase-Transfer Catalytic Diazo Transfer Synthesis." Synthetic Communications 40, no. 11 (May 6, 2010): 1574–79. http://dx.doi.org/10.1080/00397910903100742.

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5

Krasavin, Mikhail, Dmitry Dar’in, Grigory Kantin, and Olga Bakulina. "Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones." Synthesis 52, no. 15 (April 28, 2020): 2259–66. http://dx.doi.org/10.1055/s-0040-1707525.

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A convenient one-pot approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the ‘sulfonyl-azide-free’ (‘SAFE’) protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile access to a wide variety of valuable diazo reagents for organic synthesis.

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6

Tarrant, Elaine, Claire V. O'Brien, and Stuart G. Collins. "Studies towards a greener diazo transfer methodology." RSC Advances 6, no. 37 (2016): 31202–9. http://dx.doi.org/10.1039/c6ra03678c.

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7

Landman, Iris R., Farzaneh Fadaei-Tirani, and Kay Severin. "Nitrous oxide as a diazo transfer reagent: the synthesis of triazolopyridines." Chemical Communications 57, no. 87 (2021): 11537–40. http://dx.doi.org/10.1039/d1cc04907k.

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8

Chiang, Yvonne, A. Jerry Kresge, Oleg Sadovski, Xiaofeng Zeng, and Yu Zhu. "Kinetics and mechanism of acid-catalyzed hydrolysis of the diazo functional groups of 1-diazo-2-indanone and 2-diazo-1-indanone in aqueous solution." Canadian Journal of Chemistry 83, no. 9 (September 1, 2005): 1202–6. http://dx.doi.org/10.1139/v05-115.

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Rates of hydrolysis of 1-diazo-2-indanone and 2-diazo-1-indanone were measured in dilute aqueous perchloric acid solutions using both H2O and D2O as the solvent, and rates of hydrolysis of the latter substrate were measured in dilute aqueous (H2O only) formic acid buffer solutions as well. The data for 1-diazo-2-indanone gave the hydronium ion catalytic coefficient kH+ = 5.7 × 103 (mol/L)1 s1 and the isotope effect kH+/kD+ = 2.9. The normal direction (kH/kD > 1) of this isotope effect was taken as evidence for a reaction mechanism involving rate-determining hydron transfer from the hydronium ion to the substrate's diazo carbon atom; followed by rapid displacement of diazo nitrogen by a water molecule, giving the observed 1-hydroxy-2-indanone product. The data for 2-diazo-1-indanone, on the other hand, gave a hydronium ion catalytic coefficient two orders of magnitude greater than the value for 1-diazo-2-indanone (kH+ = 5.9 × 101 (mol/L)1 s1), and an isotope effect near unity (kH+/kD+ = 1.2). It is argued that this isotope effect represents a situation in which diazo carbon hydronation and displacement of diazo nitrogen are each partly rate determining, a conclusion supported by incipient saturation of buffer catalysis in the formic acid buffer solutions. The 100-fold difference in hydronium ion catalytic coefficients for the two substrates is rationalized in terms of differing electron densities on the diazo carbon atoms.Key words: diazo compound hydrolysis, solution kinetics, acid catalysis, solvent isotope effects, buffer catalysis saturation.

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9

Green, Sebastian P., Katherine M. Wheelhouse, Andrew D. Payne, Jason P. Hallett, Philip W. Miller, and James A. Bull. "Thermal Stability and Explosive Hazard Assessment of Diazo Compounds and Diazo Transfer Reagents." Organic Process Research & Development 24, no. 1 (November 28, 2019): 67–84. http://dx.doi.org/10.1021/acs.oprd.9b00422.

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10

Pandiakumar, Arun Kumar, Siddhartha P. Sarma, and Ashoka G. Samuelson. "Mechanistic studies on the diazo transfer reaction." Tetrahedron Letters 55, no. 18 (April 2014): 2917–20. http://dx.doi.org/10.1016/j.tetlet.2014.03.057.

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11

Koskinen, Ari M. P., and Luis Muñoz. "Diazo transfer reactions under mildly basic conditions." J. Chem. Soc., Chem. Commun., no. 8 (1990): 652–53. http://dx.doi.org/10.1039/c39900000652.

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12

Deadman, Benjamin J., Rosella M. O'Mahony, Denis Lynch, Daniel C. Crowley, Stuart G. Collins, and Anita R. Maguire. "Taming tosyl azide: the development of a scalable continuous diazo transfer process." Organic & Biomolecular Chemistry 14, no. 13 (2016): 3423–31. http://dx.doi.org/10.1039/c6ob00246c.

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13

Wang, Ban, Isaac G. Howard, Jackson W. Pope, Eric D. Conte, and Yongming Deng. "Bis(imino)pyridine iron complexes for catalytic carbene transfer reactions." Chemical Science 10, no. 34 (2019): 7958–63. http://dx.doi.org/10.1039/c9sc02189b.

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14

Ramachary, Dhevalapally B., Vidadala V. Narayana, and Kinthada Ramakumar. "Direct ionic liquid promoted organocatalyzed diazo-transfer reactions: diversity-oriented synthesis of diazo-compounds." Tetrahedron Letters 49, no. 17 (April 2008): 2704–9. http://dx.doi.org/10.1016/j.tetlet.2008.02.159.

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15

Xie, Shibo, Ziqiang Yan, Yuanheng Li, Qun Song, and Mingming Ma. "Intrinsically Safe and Shelf-Stable Diazo-Transfer Reagent for Fast Synthesis of Diazo Compounds." Journal of Organic Chemistry 83, no. 18 (August 18, 2018): 10916–21. http://dx.doi.org/10.1021/acs.joc.8b01587.

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16

Jaszay, Zsuzsa M., Truong Son Pham, Katalin Goenczi, Imre Petnehazy, and Laszlo Toeke. "ChemInform Abstract: Efficient Solid/Liquid Phase-Transfer Catalytic Diazo Transfer Synthesis." ChemInform 41, no. 43 (September 30, 2010): no. http://dx.doi.org/10.1002/chin.201043048.

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17

Dasgupta, Ayan, Emma Richards, and Rebecca L. Melen. "Triarylborane Catalyzed Carbene Transfer Reactions Using Diazo Precursors." ACS Catalysis 12, no. 1 (December 17, 2021): 442–52. http://dx.doi.org/10.1021/acscatal.1c04746.

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18

Rianelli, Renata de S., Maria Cecília B. V. de Souza, and Vitor F. Ferreira. "Mild Diazo Transfer Reaction Catalyzed by Modified Clays." Synthetic Communications 34, no. 5 (December 31, 2004): 951–59. http://dx.doi.org/10.1081/scc-120028368.

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19

Empel, Claire, Katharina J. Hock, and Rene M. Koenigs. "Iron-catalysed carbene-transfer reactions of diazo acetonitrile." Organic & Biomolecular Chemistry 16, no. 39 (2018): 7129–33. http://dx.doi.org/10.1039/c8ob01991f.

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20

Taber, Douglass F., Robert E. Ruckle, and Michael J. Hennessy. "Mesyl azide: a superior reagent for diazo transfer." Journal of Organic Chemistry 51, no. 21 (October 1986): 4077–78. http://dx.doi.org/10.1021/jo00371a034.

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21

GHOSH, S., and I. DATTA. "ChemInform Abstract: Diazo Transfer Reaction in Solid State." ChemInform 22, no. 48 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199148101.

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22

VILLALGORDO, J. M., A. ENDERLI, A. LINDEN, and H. HEIMGARTNER. "ChemInform Abstract: Diazo-Transfer Reaction with Diphenyl Phosphorazidate." ChemInform 27, no. 12 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199612048.

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23

Shevalev, Robert M., Petr A. Zhmurov, Dmitry V. Dar’in, and Mikhail Krasavin. "Taking diazo transfer to water: α-diazo carbonyl compounds from in situ generated mesyl azide." Mendeleev Communications 30, no. 3 (May 2020): 372–73. http://dx.doi.org/10.1016/j.mencom.2020.05.037.

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24

Kuruba, Bharath Kumar, Nusrathulla Shariff, Samuel Vasanthkumar, and Lourdusamy Emmanuvel. "NaOH/Et3N-Promoted Stereoselective One-Pot Synthesis ofα-Diazo Oxime Ethers via Diazo Transfer Reaction." Synthetic Communications 45, no. 21 (September 2015): 2454–61. http://dx.doi.org/10.1080/00397911.2015.1085575.

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25

Chiara, Jose Luis, and José Ramón Suárez. "Synthesis of α-Diazo Carbonyl Compounds with the Shelf-Stable Diazo Transfer Reagent Nonafluorobutanesulfonyl Azide." Advanced Synthesis & Catalysis 353, no. 4 (March 2, 2011): 575–79. http://dx.doi.org/10.1002/adsc.201000846.

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26

Dar’in, Dmitry, Grigory Kantin, and Mikhail Krasavin. "A ‘sulfonyl-azide-free’ (SAFE) aqueous-phase diazo transfer reaction for parallel and diversity-oriented synthesis." Chemical Communications 55, no. 36 (2019): 5239–42. http://dx.doi.org/10.1039/c9cc02042j.

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27

Monteiro, H. J. "Preparation of α-Diazo-β-Ketosulfones by Diazo-Transfer Reaction with Anin situGenerated Azidinium Salt. A Safe and Efficient Procedure for the Diazo-Transfer Reaction in Neutral Medium." Synthetic Communications 17, no. 8 (June 1987): 983–92. http://dx.doi.org/10.1080/00397918708063957.

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28

González-Granda, Sergio, Taíssa A. Costin, Marcus M. Sá, and Vicente Gotor-Fernández. "Stereoselective Bioreduction of α-diazo-β-keto Esters." Molecules 25, no. 4 (February 19, 2020): 931. http://dx.doi.org/10.3390/molecules25040931.

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Diazo compounds are versatile reagents in chemical synthesis and biology due to the tunable reactivity of the diazo functionality and its compatibility with living systems. Much effort has been made in recent years to explore their accessibility and synthetic potential; however, their preparation through stereoselective enzymatic asymmetric synthesis has been scarcely reported in the literature. Alcohol dehydrogenases (ADHs, also called ketoreductases, KREDs) are powerful redox enzymes able to reduce carbonyl compounds in a highly stereoselective manner. Herein, we have developed the synthesis and subsequent bioreduction of nine α-diazo-β-keto esters to give optically active α-diazo-β-hydroxy esters with potential applications as chiral building blocks in chemical synthesis. Therefore, the syntheses of prochiral α-diazo-β-keto esters bearing different substitution patterns at the adjacent position of the ketone group (N3CH2, ClCH2, BrCH2, CH3OCH2, NCSCH2, CH3, and Ph) and in the alkoxy portion of the ester functionality (Me, Et, and Bn), were carried out through the diazo transfer reaction to the corresponding β-keto esters in good to excellent yields (81–96%). After performing the chemical reduction of α-diazo-β-keto esters with sodium borohydride and developing robust analytical conditions to monitor the biotransformations, their bioreductions were exhaustively studied using in-house made Escherichia coli overexpressed and commercially available KREDs. Remarkably, the corresponding α-diazo-β-hydroxy esters were obtained in moderate to excellent conversions (60 to >99%) and high selectivities (85 to >99% ee) after 24 h at 30 °C. The best biotransformations in terms of conversion and enantiomeric excess were successfully scaled up to give the expected chiral alcohols with almost the same activity and selectivity values observed in the enzyme screening experiments.

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29

Dar’in, Dmitry, Grigory Kantin, and Mikhail Krasavin. "Practical Application of the Aqueous ‘Sulfonyl-Azide-Free’ (SAFE) Diazo Transfer Protocol to Less α-C–H Acidic Ketones and Esters." Synthesis 51, no. 22 (August 28, 2019): 4284–90. http://dx.doi.org/10.1055/s-0039-1690613.

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The earlier described ‘sulfonyl-azide-free’ (‘SAFE’) protocol for diazo transfer to CH-acidic 1,3-dicarbonyl compounds (and their similarly activated congeners) has been extended to the less reactive monocarbonyl substrates, which previously required a separate activation step. Formylation in situ, followed by the addition of an optimized amount of the ‘SAFE cocktail’ (obtained by mixing sodium azide, potassium carbonate, and m-carboxybenzenesulfonyl chloride in water) led to the formation of the desired diazo compounds, which were isolated by extraction in moderate to excellent yields, and, in most cases, with no need for additional purification.

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30

H. Faialaga, Nathan. "Discussion Addendum for: Detrifluoroacetylative Diazo Group Transfer: (E)-1-Diazo-4-phenyl-3-buten-2-one." Organic Syntheses 99 (2022): 234–50. http://dx.doi.org/10.15227/orgsyn.099.0234.

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31

Yan, Ziqiang, Shibo Xie, Yuanheng Li, Qun Song, and Mingming Ma. "Correction to Intrinsically Safe and Shelf-Stable Diazo-Transfer Reagent for Fast Synthesis of Diazo Compounds." Journal of Organic Chemistry 84, no. 11 (May 23, 2019): 7541. http://dx.doi.org/10.1021/acs.joc.9b00914.

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32

Tolman, Vladimír, and Petr Sedmera. "Some New Derivatives of 2-Pentenedioic Acid." Collection of Czechoslovak Chemical Communications 58, no. 6 (1993): 1430–36. http://dx.doi.org/10.1135/cccc19931430.

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Michael addition of N-acylaminomalonates to propynoic esters led to the (E)-4-acylamino)-4-carboxy-2-pentenedioic triesters IIa - IIf. On deprotection and decarboxylation, these compounds afforded 2-(N-acylamino)-2-pentenedioic acid derivatives IIIa - IIIc. Dimethyl (E)-4-diazo-2-pentenedioate (IV) was prepared by direct transfer of the diazo group. On treatment of IV with 4-toluenesulfonic acid, 2-(4-toluenesulfonyloxy)-2-pentenedioate (V) was formed. Iodination of (E)-2-pentenedioic acid led directly to the 2,4-diododerivative VII. From dimethyl (E)-4-oxo-2-pentenedioate the oximino ester VIIIa and the free oximino acid VIIIb were prepared.

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33

Mrówczyński, R., L. Magerusan, R. Turcu, and J. Liebscher. "Diazo transfer at polydopamine – a new way to functionalization." Polym. Chem. 5, no. 22 (July 30, 2014): 6593–99. http://dx.doi.org/10.1039/c4py00670d.

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34

Kitamura, Mitsuru, Rie Sakata, Norifumi Tashiro, Azusa Ikegami, and Tatsuo Okauchi. "Synthesis of Diazonaphthoquinones from Naphthols by Diazo-Transfer Reaction." Bulletin of the Chemical Society of Japan 88, no. 6 (June 15, 2015): 824–33. http://dx.doi.org/10.1246/bcsj.20150021.

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35

Chiara, Jose Luis, and Jose Ramon Suarez. "ChemInform Abstract: Synthesis of α-Diazo Carbonyl Compounds with the Shelf-Stable Diazo Transfer Reagent Nonafluorobutanesulfonyl Azide." ChemInform 42, no. 24 (May 19, 2011): no. http://dx.doi.org/10.1002/chin.201124053.

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36

Fructos, Manuel R., M. Mar Díaz-Requejo, and Pedro J. Pérez. "Gold and diazo reagents: a fruitful tool for developing molecular complexity." Chemical Communications 52, no. 46 (2016): 7326–35. http://dx.doi.org/10.1039/c6cc01958g.

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After a decade since its discovery and being yet at its sunrise, the use of gold catalysis for the transfer of carbene groups from diazo compounds is becoming a powerful synthetic tool. The main advances in the area and future directions are provided in this Feature Article.

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37

McGuiness, Mark, and Harold Shechter. "Azidotris(diethylamino)phosphonium bromide: A self-catalyzing diazo transfer reagent." Tetrahedron Letters 31, no. 35 (January 1990): 4987–90. http://dx.doi.org/10.1016/s0040-4039(00)97785-2.

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38

Coquerel, Yoann, Jean Rodriguez, Marc Presset, and Damien Mailhol. "Diazo-Transfer Reactions to 1,3-Dicarbonyl Compounds with Tosyl Azide." Synthesis 2011, no. 16 (July 14, 2011): 2549–52. http://dx.doi.org/10.1055/s-0030-1260107.

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39

Adam, Waldemar, and Elena Gonzalez Nuñez. "Oxygen transfer by dissociative electron transfer. Reaction of tetranitromethane with diazo compounds and sulfides." Tetrahedron 47, no. 23 (1991): 3773–78. http://dx.doi.org/10.1016/s0040-4020(01)80902-9.

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40

Benati, Luisa, Gianluca Calestani, Pier Carlo Montevecchi, and Piero Spagnolo. "Diazo transfer reaction of 2-(trimethylsilyl)-1,3-dithiane with tosyl azide. Reactivity of transient 2-diazo-1,3-dithiane." Journal of the Chemical Society, Chemical Communications, no. 19 (1995): 1999. http://dx.doi.org/10.1039/c39950001999.

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41

Kuruba, Bharath Kumar, Nusrathulla Shariff, Samuel Vasanthkumar, and Lourdusamy Emmanuvel. "ChemInform Abstract: NaOH/Et3N-Promoted Stereoselective One-Pot Synthesis of α-Diazo Oxime Ethers via Diazo Transfer Reaction." ChemInform 47, no. 10 (February 2016): no. http://dx.doi.org/10.1002/chin.201610059.

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42

Nagarajan, R., and L. Emmanuvel. "Unusual Cleavage of N-N Bond of 1-Arylamino-1,2,3-triazole Derivatives: A Simple and Alternate Approach to 4,5-Disubstituted-1H-1,2,3-triazoles." Asian Journal of Chemistry 31, no. 5 (March 28, 2019): 1057–61. http://dx.doi.org/10.14233/ajchem.2019.21857.

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In this communication, the authors described the synthesis of 1-arylamino-1,2,3-triazole derivatives via diazo transfer reaction on active methylene hydrazones. Further, we have observed the reduction of 1-arylamino-1,2,3-triazole using Pd/C, H2 to result in unusual N-N bond cleavage to give 4,5-disubstituted-1H-1,2,3-triazole.

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43

Benati, Luisa, Gianluca Calestani, Daniele Nanni, Piero Spagnolo, and Marco Volta. "Diazo transfer reaction of 2-(trimethylsilyl)-1,3-dithiane with tosyl azide. Carbenic reactivity of transient 2-diazo-1,3-dithiane." Tetrahedron 53, no. 27 (July 1997): 9269–78. http://dx.doi.org/10.1016/s0040-4020(97)00538-3.

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44

Zhmurov, Petr A., Dmitry V. Dar’in, Olga Yu Bakulina, and Mikhail Krasavin. "One-pot preparation of methyl 2-diazo-3-oxopropionates comprising an aqueous ‘sulfonyl-azide-free’ (SAFE) diazo transfer step." Mendeleev Communications 30, no. 3 (May 2020): 311–12. http://dx.doi.org/10.1016/j.mencom.2020.05.016.

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45

Damiano, Caterina, Paolo Sonzini, and Emma Gallo. "Iron catalysts with N-ligands for carbene transfer of diazo reagents." Chemical Society Reviews 49, no. 14 (2020): 4867–905. http://dx.doi.org/10.1039/d0cs00221f.

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This review provides an overview of the catalytic activity of iron complexes of nitrogen ligands in driving carbene transfers towards CC, C–H and X–H bonds. The reactivity of diazo reagents is discussed as well as the proposed reaction mechanisms.

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46

Beletskaya, Irina P., and Igor D. Titanyuk. "Synthesis of α-Aryldiazophosphonates via a Diazo Transfer Reaction." Journal of Organic Chemistry 87, no. 5 (February 22, 2022): 2748–57. http://dx.doi.org/10.1021/acs.joc.1c02673.

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47

van Dongen, Stijn F. M., Rosalie L. M. Teeuwen, Madhavan Nallani, Sander S. van Berkel, Jeroen J. L. M. Cornelissen, Roeland J. M. Nolte, and Jan C. M. van Hest. "Single-Step Azide Introduction in Proteins via an Aqueous Diazo Transfer." Bioconjugate Chemistry 20, no. 1 (January 21, 2009): 20–23. http://dx.doi.org/10.1021/bc8004304.

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48

Lartia, Rémy, Pierre Murat, Pascal Dumy, and Eric Defrancq. "Versatile Introduction of Azido Moiety into Oligonucleotides through Diazo Transfer Reaction." Organic Letters 13, no. 20 (October 21, 2011): 5672–75. http://dx.doi.org/10.1021/ol202397e.

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49

Kitamura, Mitsuru, Rie Sakata, Norifumi Tashiro, Azusa Ikegami, and Tatsuo Okauchi. "ChemInform Abstract: Synthesis of Diazonaphthoquinones from Naphthols by Diazo-Transfer Reaction." ChemInform 46, no. 45 (October 22, 2015): no. http://dx.doi.org/10.1002/chin.201545108.

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50

Alper, Phil B., Shang-Cheng Hung, and Chi-Huey Wong. "Metal catalyzed diazo transfer for the synthesis of azides from amines." Tetrahedron Letters 37, no. 34 (August 1996): 6029–32. http://dx.doi.org/10.1016/0040-4039(96)01307-x.

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