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Journal articles on the topic 'Diazo compounds'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

Osipov, Sergey, and Daria Vorobyeva. "Selective Synthesis of 2- and 7-Substituted Indole Derivatives via Chelation-Assisted Metallocarbenoid C–H Bond Functionalization." Synthesis 50, no. 02 (2017): 227–40. http://dx.doi.org/10.1055/s-0036-1591498.

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Functionally substituted indole derivatives are important intermediates for the synthesis of new potential drug candidates exhibiting strong bioactivities. Over the past few years, significant progress has been made in the direct C–H functionalization of the indole ring through the usage of metal-catalyzed intermolecular cross-coupling with diazo compounds. Directing group strategy provides a unique possibility for selective insertion of carbenes catalytically generated from diazo compounds into challenging indole C2–H and C7–H bonds. This short review summarizes recent advances in carbenoid f

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2

Valdés, Carlos, Miguel Paraja, and Manuel Plaza. "Transition-Metal-Free Reactions Between Boronic Acids and N-Sulfonylhydrazones or Diazo Compounds: Reductive Coupling Processes and Beyond." Synlett 28, no. 18 (2017): 2373–89. http://dx.doi.org/10.1055/s-0036-1590868.

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The metal-free reaction between diazo compounds and boronic acids has been established in recent years as a powerful C(sp3)–C bond-forming reaction. This account covers the recent advances in this area. First, the various synthetic applications of reactions with N-sulfonylhydrazones as a convenient source of diazo compounds is discussed. These transformations can be regarded as reductive couplings of carbonyl compounds. Also covered is the incorporation of other mild sources of diazo compounds in these reactions: diazotization of amines and oxidation of hydrazones. Finally, the development of

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3

Zhukovsky, Daniil, Dmitry Dar’in, Olga Bakulina та Mikhail Krasavin. "Preparation and Synthetic Applications of Five-to-Seven-Membered Cyclic α-Diazo Monocarbonyl Compounds". Molecules 27, № 6 (2022): 2030. http://dx.doi.org/10.3390/molecules27062030.

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The reactivity of cyclic α-diazo monocarbonyl compounds differs from that of their acyclic counterparts. In this review, we summarize the current literature available on the synthesis and synthetic applications of three major classes of cyclic α-diazo monocarbonyl compounds: α-diazo ketones, α-diazo lactones and α-diazo lactams.

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4

Wang, Jianbo. "When diazo compounds meet with organoboron compounds." Pure and Applied Chemistry 90, no. 4 (2018): 617–23. http://dx.doi.org/10.1515/pac-2017-0713.

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AbstractTransition-metal free reactions of diazo compounds with organoboron compounds provide some unique approaches for the formation of C–C, C–B and C–Si bonds. WithN-tosylhydrazones as the precursors for non-stabilized diazo compound, this type of reaction becomes practically useful in organic synthesis. Transition-metal-free synthetic methodologies for borylation,gem-diborylation,gem-silylborylation arylation, 2,2,2-trifluoroethylation andgem-difluorovinylation have been successfully developed.

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5

Ciszewski, Łukasz W., Katarzyna Rybicka-Jasińska, and Dorota Gryko. "Recent developments in photochemical reactions of diazo compounds." Organic & Biomolecular Chemistry 17, no. 3 (2019): 432–48. http://dx.doi.org/10.1039/c8ob02703j.

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Chemistry of diazo compounds is dominated by transition metal catalysis but recently, photoinitiated reactions of diazo compounds have attracted a lot of attention. This mini-review describes recent discoveries on the reactivity of diazo compounds under light irradiation.

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6

Durka, Jakub, Joanna Turkowska, and Dorota Gryko. "Lightening Diazo Compounds?" ACS Sustainable Chemistry & Engineering 9, no. 27 (2021): 8895–918. http://dx.doi.org/10.1021/acssuschemeng.1c01976.

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7

Sutton, Derek. "Organometallic diazo compounds." Chemical Reviews 93, no. 3 (1993): 995–1022. http://dx.doi.org/10.1021/cr00019a008.

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8

Yates, Peter, and J. A. Eenkhorn. "Aliphatic diazo compounds." Tetrahedron 44, no. 11 (1988): 3159–70. http://dx.doi.org/10.1016/s0040-4020(01)85947-0.

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9

Böhshar, Manfred, Heinrich Heydt, and Manfred Regitz. "Diazo compounds-66." Tetrahedron 42, no. 6 (1986): 1815–22. http://dx.doi.org/10.1016/s0040-4020(01)87600-6.

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10

Zhu, Shou-Fei, and Qi-Lin Zhou. "Iron-catalyzed transformations of diazo compounds." National Science Review 1, no. 4 (2014): 580–603. http://dx.doi.org/10.1093/nsr/nwu019.

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Abstract Although iron-promoted diazo transformations were only discovered during the 1990s, iron can undergo facile changes in its oxidation state and possesses distinct Lewis acid character, and these properties have afforded iron a privileged position as a catalyst in the transformations of diazo compounds. In this review, we have provided an overview of the iron-catalyzed diazo transformation reactions reported in the literature by the end of 2013 with the aim of stimulating further interest in this area of research.

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11

Mukhopadhyay, Chhanda, Sayan Pramanik, Suman Ray, Suvendu Maity та Prasanta Ghosh. "Diastereoselective trans Cyclopropanation of 3-Alkylidene Oxindoles with In Situ Generated α-Diazo Carbonyls or α,β-Unsaturated Diazo Compounds". Synthesis 53, № 13 (2021): 2240–52. http://dx.doi.org/10.1055/a-1384-1967.

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AbstractAn efficient diastereoselective trans cyclopropanation of 3-alkylidene oxindoles with in situ generated α-diazo carbonyl compounds or α,β-unsaturated diazo compounds under metal-free conditions has been developed to synthesize 3-spirocyclopropyl-2-oxindole derivatives. The procedure is based on the 1,3-dipolar character of the corresponding diazo compounds under base-catalyzed conditions. The method has a wide substrate scope and uses easily available starting materials.

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12

Hua, Ting-Bi, Qing-Qing Yang, and You-Quan Zou. "Recent Advances in Enantioselective Photochemical Reactions of Stabilized Diazo Compounds." Molecules 24, no. 17 (2019): 3191. http://dx.doi.org/10.3390/molecules24173191.

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Diazo compounds have proven to be a useful class of carbenes or metal carbenoids sources under thermal, photochemical, or metal-catalyzed conditions, which can subsequently undergo a wide range of synthetically important transformations. Recently, asymmetric photocatalysis has provoked increasing research interests, and great advances have been made in this discipline towards the synthesis of optically enriched compounds. In this context, the past two decades have been the most productive period in the developments of enantioselective photochemical reactions of diazo compounds due to a better

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13

DRAHL, CARMEN. "ALKENES FROM DIAZO COMPOUNDS." Chemical & Engineering News Archive 89, no. 8 (2011): 10. http://dx.doi.org/10.1021/cen-v089n008.p010.

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14

Allouche, Emmanuelle M. D., and André B. Charette. "Cyclopropanation Reactions of Semi-stabilized and Non-stabilized Diazo Compounds." Synthesis 51, no. 21 (2019): 3947–63. http://dx.doi.org/10.1055/s-0037-1611915.

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The cyclopropane ring is present in a large number of bioactive molecules as its incorporation often greatly alters their physiochemical properties. The synthesis of such motif is therefore of interest. Diazo compounds are versatile and powerful reagents that can be used in a broad range of reactions, including cyclopropanation processes. However, in case of unstable diazo reagents such as the donor-substituted variants, their inherent toxicity and instability have hampered their effective synthesis and utilization. Herein, we report the recent advances devoted to the safe and facile produc

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15

Budeev, Anton, Grigory Kantin, Dmitry Dar’in, and Mikhail Krasavin. "Diazocarbonyl and Related Compounds in the Synthesis of Azoles." Molecules 26, no. 9 (2021): 2530. http://dx.doi.org/10.3390/molecules26092530.

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Diazocarbonyl compounds have found numerous applications in many areas of chemistry. Among the most developed fields of diazo chemistry is the preparation of azoles from diazo compounds. This approach represents a useful alternative to more conventional methods of the synthesis of azoles. A comprehensive review on the preparation of various azoles (oxazoles, thiazoles, imidazoles, pyrazoles, triazoles, and tetrazoles) from diazocarbonyl and related compounds is presented for the first time along with discussion of advantages and disadvantages of «diazo» approaches to azoles.

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16

Yan, Yiyong, Gaoyuan Ma, Wei Wei, and Jing Zhao. "Synthesis of Sulfonyldiazomethanes and Acetyldiazomethanes via an Alumina-Mediated Decarboxylation Strategy." Australian Journal of Chemistry 69, no. 2 (2016): 239. http://dx.doi.org/10.1071/ch15637.

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Diazo compounds are widely adopted in organic synthesis due to their carbine characteristics. One of the most interesting diazo compounds is diazolsulfonyl. Here, in the current study, we found that diazolsufonyl compounds could be prepared with moderate to excellent yield through decarboxylation of diazosulfonyl acetates by neutral alumina. We hope that this mild and simple method might inspire wider application of these useful compounds.

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17

Wang, Jianbo, Huan Li, and Yan Zhang. "Reaction of Diazo Compounds with Organoboron Compounds." Synthesis 45, no. 22 (2013): 3090–98. http://dx.doi.org/10.1055/s-0033-1340041.

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18

Xiao, Tiebo, Mingjing Mei, Yuwei He, and Lei Zhou. "Blue light-promoted cross-coupling of aryldiazoacetates and diazocarbonyl compounds." Chemical Communications 54, no. 64 (2018): 8865–68. http://dx.doi.org/10.1039/c8cc04609c.

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A blue light-promoted cross-coupling of two distinct diazo compounds was described. The reaction producesE-configured trisubstituted alkenes in good yields in the absence of catalysts and additives. The reactive free carbene intermediates were generatedviaselective photolysis of one of the two diazo compounds upon blue light irradiation.

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19

Guranova, Natalia Igorevna, Grigoriy Pavlovich Kantin, Olga Yurievna Bakulina, Alexander Denisovich Yanovich, and Dmitry Viktorovich Dar’in. "Late-stage <em>N</em>-functionalization of diazo NH-heterocycles: the Mitsunobu reaction <em>vs</em>. alkylation with alkyl halides." Mendeleev Communications 35, no. 2 (2025): 165–68. https://doi.org/10.71267/mencom.7586.

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Selective <em>N</em>-alkylation of various diazo NH-heterocycles with preserving the diazo function was performed either by classical alkylation with alkyl halides or by the Mitsunobu reaction with alcohols. The substrate variety involved diazo-substituted homophthalimide, arylidenesuccinimides, (thio)barbituric acids, and pyrazolones. This is the first time the Mitsunobu reaction has been applied for the functionalization of diazo carbonyl compounds.

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20

Zhuo, Chun-Xiang, and Jia-Le Wang. "Catalytic Deoxygenative Cyclopropanation of 1,2-Dicarbonyl or Monocarbonyl Compounds via Molybdenum Catalysis." Synlett 33, no. 07 (2021): 599–608. http://dx.doi.org/10.1055/a-1696-4553.

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AbstractThe cyclopropanation of alkenes through the transition-metal-catalyzed decomposition of diazo compounds is a powerful and straightforward strategy to produce cyclopropanes. Nevertheless, the appeal of further application of this strategy is tempered by the potentially explosive nature of the diazo substrates. Therefore, it is highly desirable to develop sustainable and operationally safe surrogates for diazo compounds. In this Synpacts article, we discuss recent advances on the cyclopropane syntheses through the catalytic cyclopropanation of alkenes and metal carbenes generated in situ

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21

Cressy, Derek, Cristian Zavala, Anthony Abshire, William Sheffield, and Ampofo Darko. "Tuning Rh(ii)-catalysed cyclopropanation with tethered thioether ligands." Dalton Transactions 49, no. 44 (2020): 15779–87. http://dx.doi.org/10.1039/d0dt03019h.

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22

WATANABE, MASAHARU, NORIAKI TOCHIZAWA, HIROTADA IIDA, and HIDEO KIKUCHI. "Novel Photosensitive Multifunctional Diazo Compounds." Journal of Photopolymer Science and Technology 7, no. 1 (1994): 71–74. http://dx.doi.org/10.2494/photopolymer.7.71.

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23

Lebedev, Albert T. "Mass spectrometry of diazo compounds." Mass Spectrometry Reviews 10, no. 2 (1991): 91–132. http://dx.doi.org/10.1002/mas.1280100202.

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24

SUTTON, D. "ChemInform Abstract: Organometallic Diazo Compounds." ChemInform 24, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199331334.

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25

Maas, Gerhard. "New Syntheses of Diazo Compounds." Angewandte Chemie International Edition 48, no. 44 (2009): 8186–95. http://dx.doi.org/10.1002/anie.200902785.

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26

Bug, Thorsten, Manfred Hartnagel, Clemens Schlierf, and Herbert Mayr. "How Nucleophilic Are Diazo Compounds?" Chemistry - A European Journal 9, no. 17 (2003): 4068–76. http://dx.doi.org/10.1002/chem.200304913.

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27

Roda, Nuria M., Duc N. Tran, Claudio Battilocchio, et al. "Cyclopropanation using flow-generated diazo compounds." Organic & Biomolecular Chemistry 13, no. 9 (2015): 2550–54. http://dx.doi.org/10.1039/c5ob00019j.

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28

Ollevier, Thierry, Virginie Carreras, and Nour Tanbouza. "The Power of Iron Catalysis in Diazo Chemistry." Synthesis 53, no. 01 (2020): 79–94. http://dx.doi.org/10.1055/s-0040-1707272.

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AbstractThe use of iron catalysis to enable reactions with diazo compounds has emerged as a valuable tool to forge carbon–carbon or carbon–heteroatom bonds. While diazo compounds are often encountered with toxic and expensive metal catalysts, such as Rh, Ru, Pd, Ir, and Cu, a resurgence of Fe catalysis has been observed. This short review will showcase and highlight the recent advances in iron-mediated reactions of diazo compounds.1 Introduction2 Insertion Reactions2.1 Insertion into B–H Bonds2.2 Insertion into Si–H Bonds2.3 Insertion into N–H Bonds2.4 Insertion into S–H bonds3 Ylide Formation

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29

Wang, Jianbo, and Kang Wang. "Transition-Metal-Catalyzed Cross-Coupling with Non-Diazo Carbene Precursors." Synlett 30, no. 05 (2018): 542–51. http://dx.doi.org/10.1055/s-0037-1611020.

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Transition-metal-catalyzed cross-coupling reactions through metal carbene migratory insertion have emerged as powerful methodology for carbon–carbon bond constructions. Typically, diazo compounds (or in situ generated diazo compounds from N-tosylhydrazones) have been employed as the metal carbene precursors for this type of cross-coupling reactions. Recently, cross-coupling reactions employing non-diazo carbene precursors, such as conjugated ene-yne-ketones, allenyl ketones, alkynes, cyclopropenes, and Cr(0) Fischer carbenes, have been developed. This account will summarize our efforts in the

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30

Bennett, Chester Wallace, and William Albert Noyes. "Optically active diazo compounds. IV. A stable alicyclic diazo amine." Recueil des Travaux Chimiques des Pays-Bas 48, no. 9 (2010): 895–98. http://dx.doi.org/10.1002/recl.19290480908.

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31

Swarnkar, Pawan Kumar, P. Kriplani, G. N. Gupta, and K. G. Ojha. "Synthesis and Antibacterial Activity of Some New Phenothiazine Derivatives." E-Journal of Chemistry 4, no. 1 (2007): 14–20. http://dx.doi.org/10.1155/2007/402673.

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A series of some new phenothiazine derivatives were synthesized with the objective for evaluation as antimicrobials. The title compounds were prepared by a five step synthesis scheme. 2-Amino-6-substituted benzothiazoles (1) on diazotization afford 6-substituted benzothiazolyl-2-diazonium chlorides (2). Reaction of 2 with cold solution ofβ-naphthol in dilute NaOH furnishesα-(2-diazo-6-substituted benzothiazolyl)-β-sodionaphthoxides (3) which on acidification with concentrated HCl givesα-(2-diazo-6-substituted benzothiazolyl)-β-naphthols (4). Reaction of 4 with p-substituted anilines givesα-(2-

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32

Hock, Katharina J., Lucas Mertens, Renè Hommelsheim, Robin Spitzner, and Rene M. Koenigs. "Enabling iron catalyzed Doyle–Kirmse rearrangement reactions with in situ generated diazo compounds." Chemical Communications 53, no. 49 (2017): 6577–80. http://dx.doi.org/10.1039/c7cc02801f.

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Safe rearrangement reactions of sulfides with in situ generated diazo compounds have been developed. Transient generation of, for example, diazo acetonitrile followed by iron catalysed Doyle–Kirmse reaction generates valuable building blocks for drug discovery.

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33

Shereshovets, V. V., N. M. Korotaeva, A. S. Vorob'ev, V. D. Komissarov, and I. I. Furlei. "Oxidation of diazo compounds by triphenyl phosphite ozonide. Quenching of singlet oxygen by diazo compounds." Russian Chemical Bulletin 43, no. 9 (1994): 1479–83. http://dx.doi.org/10.1007/bf00697131.

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34

Maysoon T.Tawfiq. "Synthesis and characterization of some new heterocyclic compounds." Journal of the College of Basic Education 20, no. 86 (2023): 1031–48. http://dx.doi.org/10.35950/cbej.v20i86.9745.

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This work includes preparing of some new derivatives of pyrimidine ,pyrazolidine, and isoxazolidine from the reaction between tetraethyl 2,2' -(1E,1E' )- biphenyl ll-4, 4' -diylbis(diazene-1,2-diyl)dimalonate(1) and ammonia derivatives in dry ethanol to obtain the six membered hetero rings: 5,5'-(1E,1E') biphenyl-4,4'-diylbis (diazo-1,2-diyl)bis(2-mercaptopyrimidine-4,6-diol)(2) ; 5,5'-(1E,1E' ) biphenyl-4,4'-diylbis(diazo-1,2-diyl)dipyrimidine-2,4,6-triol(3);5,5'-(1E,1E')-biphenyl-4,4'-diylbis (diazo-1,2-diyl)bis(2-aminopyridine-4,6-diol)(4); and five membered hetero ring: 4,4' -(1E,1E')-biph

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35

Simões, Mário M. Q., José A. S. Cavaleiro, and Vitor F. Ferreira. "Recent Synthetic Advances on the Use of Diazo Compounds Catalyzed by Metalloporphyrins." Molecules 28, no. 18 (2023): 6683. http://dx.doi.org/10.3390/molecules28186683.

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Diazo compounds are organic substances that are often used as precursors in organic synthesis like cyclization reactions, olefinations, cyclopropanations, cyclopropenations, rearrangements, and carbene or metallocarbene insertions into C−H, N−H, O−H, S−H, and Si−H bonds. Typically, reactions from diazo compounds are catalyzed by transition metals with various ligands that modulate the capacity and selectivity of the catalyst. These ligands can modify and enhance chemoselectivity in the substrate, regioselectivity and enantioselectivity by reflecting these preferences in the products. Porphyrin

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36

Allouche, Emmanuelle M. D., Afnan Al-Saleh, and André B. Charette. "Iron-catalyzed synthesis of cyclopropanes by in situ generation and decomposition of electronically diversified diazo compounds." Chemical Communications 54, no. 94 (2018): 13256–59. http://dx.doi.org/10.1039/c8cc07060a.

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The modular synthesis of a variety of trans 1,2-disubstituted cyclopropanes in a one-pot iron-catalyzed cyclopropanation is described. N-nosylhydrazones are used as diazo precursors, allowing the in situ generation of electron-rich diazo compounds and their direct participation in the reaction.

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37

Gomes, Ana T. P. C., Maria G. P. M. S. Neves, and José A. S. Cavaleiro. "Diazo compounds in the functionalization of porphyrin macrocycles." Journal of Porphyrins and Phthalocyanines 15, no. 09n10 (2011): 835–47. http://dx.doi.org/10.1142/s1088424611003884.

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38

McGrath, Nicholas A., Kristen A. Andersen, Amy K. F. Davis, Jo E. Lomax, and Ronald T. Raines. "Diazo compounds for the bioreversible esterification of proteins." Chemical Science 6, no. 1 (2015): 752–55. http://dx.doi.org/10.1039/c4sc01768d.

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39

Marco-Contelles, Jose, and Maria Molina. "Naturally Occurring Diazo Compounds: The Kinamycins." Current Organic Chemistry 7, no. 14 (2003): 1433–42. http://dx.doi.org/10.2174/1385272033486396.

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40

Gao, Yunpeng, and Jianbo Wang. "Continuous Flow Reaction of Diazo Compounds." Chinese Journal of Organic Chemistry 38, no. 6 (2018): 1275. http://dx.doi.org/10.6023/cjoc201712029.

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41

Pisella, Guillaume, Alec Gagnebin, and Jerome Waser. "Copper-Catalyzed Oxyvinylation of Diazo Compounds." Organic Letters 22, no. 10 (2020): 3884–89. http://dx.doi.org/10.1021/acs.orglett.0c01150.

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42

Wei, Fang, Chuanling Song, Yudao Ma, Ling Zhou, Chen-Ho Tung, and Zhenghu Xu. "Gold carbene chemistry from diazo compounds." Science Bulletin 60, no. 17 (2015): 1479–92. http://dx.doi.org/10.1007/s11434-015-0874-0.

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43

Müller, Simon T. R., and Thomas Wirth. "Diazo Compounds in Continuous-Flow Technology." ChemSusChem 8, no. 2 (2014): 245–50. http://dx.doi.org/10.1002/cssc.201402874.

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44

Secka, Jim, Arpan Pal, Francis A. Acquah, et al. "Coupling of acceptor-substituted diazo compounds and tertiary thioamides: synthesis of enamino carbonyl compounds and their pharmacological evaluation." RSC Advances 12, no. 30 (2022): 19431–44. http://dx.doi.org/10.1039/d2ra02415b.

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45

Krasavin, Mikhail, Maria Eremeyeva, Daniil Zhukovsky та Dmitry Dar’in. "The Use of α-Diazo-γ-butyrolactams in the Büchner–Curtius–Schlotterbeck Reaction of Cyclic Ketones Opens New Entry to Spirocyclic Pyrrolidones". Synlett 31, № 10 (2020): 982–86. http://dx.doi.org/10.1055/s-0040-1708011.

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The only cyclic α-diazocarbonyl compound employed in the Büchner–Curtius–Schlotterbeck ring expansion of cyclic ketones to date was α-diazo-γ-butyrolactone. Encouraged by the recent success using α-diazo acetamides in related Tiffeneau–Demjanov type ring expansions, we extended this approach to various α-diazo-γ-butyrolactams, which produced, under BF3·OEt2-promoted conditions, spirocyclic seven-membered ketones. These findings substantially enhance the possibilities offered by cyclic α-diazocarbonyl compounds in constructing privileged spirocyclic scaffolds for drug design.

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46

Li, Huan, Yan Zhang, and Jianbo Wang. "ChemInform Abstract: Reaction of Diazo Compounds with Organoboron Compounds." ChemInform 45, no. 5 (2014): no. http://dx.doi.org/10.1002/chin.201405243.

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47

González-Granda, Sergio, Taíssa A. Costin, Marcus M. Sá та Vicente Gotor-Fernández. "Stereoselective Bioreduction of α-diazo-β-keto Esters". Molecules 25, № 4 (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

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48

Murphy, Graham, та Keith Coffey. "Dichlorination of α-Diazo-β-dicarbonyls Using (Dichloroiodo)benzene". Synlett 26, № 08 (2015): 1003–7. http://dx.doi.org/10.1055/s-0034-1380304.

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α-Diazo-β-dicarbonyl compounds were chlorinated using (dichloro)iodobenzene and an activating catalyst. A broad range of reaction rates was observed, which paralleled the relative stability/nucleophilicity of the diazo compounds. Acyclic diazocarbonyls reacted faster than cyclics, and β-diketones were much faster to react than β-keto esters or β-diesters. Lewis acid activation was used for the first time, allowing us to overcome instances of poor chemoselectivity. Though the yields ranged from low to good, this chlorination reaction has again proven a mild and effective halogenation strategy.

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49

Dar’in, Dmitry, Grigory Kantin та 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, № 22 (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, i

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Nelson, Adam, Shiao Chow, Adam I. Green та ін. "Efficient Approaches for the Synthesis of Diverse α-Diazo Amides". Synthesis 52, № 11 (2020): 1695–706. http://dx.doi.org/10.1055/s-0039-1690905.

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Abstract:

Metal-catalysed carbenoid chemistry can be exploited for the synthesis of diverse ranges of small molecules from α-diazo carbonyl compounds. In this paper, three synthetic approaches to α-diazo amides are described, and their scope and limitations are determined. On the basis of these synthetic studies, recommendations are provided to assist the selection of the most appropriate approach for specific classes of product. The availability of practical and efficient syntheses of diverse α-diazo acetamides is expected to facilitate the discovery of many different classes of bioactive small molecul

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