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Journal articles on the topic 'Α-diazocarbonyl compounds'

Author: Grafiati

Published: 6 September 2023

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1

Krasavin, Mikhail, Maria Eremeyeva, Daniil Zhukovsky, and 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, no. 10 (March 23, 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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2

Wang, Zikun, Xihe Bi, Yongjiu Liang, Peiqiu Liao, and Dewen Dong. "A copper-catalyzed formal O–H insertion reaction of α-diazo-1,3-dicarbonyl compounds to carboxylic acids with the assistance of isocyanide." Chem. Commun. 50, no. 30 (2014): 3976–78. http://dx.doi.org/10.1039/c4cc00402g.

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Straightforward synthetic access to α-acyloxy-1,3-dicarbonyl compounds is described via a novel Cu(ii)-catalyzed and isocyanide-assisted formal O–H insertion reaction of α-diazocarbonyl compounds to carboxylic acids.

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3

Dong, Shunxi, Xiaohua Liu, and Xiaoming Feng. "Asymmetric Catalytic Rearrangements with α-Diazocarbonyl Compounds." Accounts of Chemical Research 55, no. 3 (January 14, 2022): 415–28. http://dx.doi.org/10.1021/acs.accounts.1c00664.

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4

Ford, Alan, Hugues Miel, Aoife Ring, Catherine N. Slattery, Anita R. Maguire, and M. Anthony McKervey. "Modern Organic Synthesis with α-Diazocarbonyl Compounds." Chemical Reviews 115, no. 18 (August 18, 2015): 9981–10080. http://dx.doi.org/10.1021/acs.chemrev.5b00121.

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5

Lübcke, Marvin, Dina Bezhan, and Kálmán J. Szabó. "Trifluoromethylthiolation–arylation of diazocarbonyl compounds by modified Hooz multicomponent coupling." Chemical Science 10, no. 23 (2019): 5990–95. http://dx.doi.org/10.1039/c9sc00829b.

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Multicomponent reaction of diazocarbonyl and dibenzenesulfonimide-SCF₃ reagents with BAr₄ salts in the presence of Zn(NTf₂)₂ gives α,α′-difunctionalized trifluoromethylthio compounds.

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6

Chen, Xun, Ying Xie, Xinsheng Xiao, Guoqiang Li, Yuanfu Deng, Huanfeng Jiang, and Wei Zeng. "Rh(iii)-catalyzed chelation-assisted intermolecular carbenoid functionalization of α-imino Csp3–H bonds." Chemical Communications 51, no. 83 (2015): 15328–31. http://dx.doi.org/10.1039/c5cc06428g.

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7

Liu, Lu, and Junliang Zhang. "Gold-catalyzed transformations of α-diazocarbonyl compounds: selectivity and diversity." Chemical Society Reviews 45, no. 3 (2016): 506–16. http://dx.doi.org/10.1039/c5cs00821b.

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Gold-catalyzed diazo transformations display very unique reactivity and selectivity compared to other noble metals. This review will summarize gold-catalyzed transformations of α-diazocarbonyl compounds.

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8

Wang, Kang, Shufeng Chen, Hang Zhang, Shuai Xu, Fei Ye, Yan Zhang, and Jianbo Wang. "Pd(0)-catalyzed cross-coupling of allyl halides with α-diazocarbonyl compounds or N-mesylhydrazones: synthesis of 1,3-diene compounds." Organic & Biomolecular Chemistry 14, no. 15 (2016): 3809–20. http://dx.doi.org/10.1039/c6ob00454g.

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An efficient method for the synthesis of 1,3-butadiene derivatives based on Pd-catalyzed cross-coupling with allyl bromides or chlorides with α-diazocarbonyl compounds or N-mesylhydrazones is presented.

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9

Cortés González, Miguel A., Xingguo Jiang, Patrik Nordeman, Gunnar Antoni, and Kálmán J. Szabó. "Rhodium-mediated 18F-oxyfluorination of diazoketones using a fluorine-18-containing hypervalent iodine reagent." Chemical Communications 55, no. 89 (2019): 13358–61. http://dx.doi.org/10.1039/c9cc06905d.

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10

Ghorai, Jayanta, Manthena Chaitanya, and Pazhamalai Anbarasan. "Cp*Co(iii)-catalysed selective alkylation of C–H bonds of arenes and heteroarenes with α-diazocarbonyl compounds." Organic & Biomolecular Chemistry 16, no. 40 (2018): 7346–50. http://dx.doi.org/10.1039/c8ob02111b.

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11

YE, T., and M. A. MCKERVEY. "ChemInform Abstract: Organic Synthesis with α-Diazocarbonyl Compounds." ChemInform 25, no. 39 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199439313.

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12

YE, T., and M. A. MCKERVEY. "ChemInform Abstract: Organic Synthesis with α-Diazocarbonyl Compounds." ChemInform 25, no. 44 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199444267.

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13

KIM, S., and J. R. CHO. "ChemInform Abstract: Radical Cyclization of α-Diazocarbonyl Compounds." ChemInform 25, no. 21 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199421077.

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14

Zhang, He, Tongxiang Cao, Hejiang Luo, Lianfen Chen, and Shifa Zhu. "Enynone-enabled migratory insertion and Schmittel cyclization cascade for the synthesis of furan-fused fluorenes." Organic Chemistry Frontiers 6, no. 8 (2019): 1118–22. http://dx.doi.org/10.1039/c9qo00045c.

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15

Hou, Wei, Yaxi Yang, Yunxiang Wu, Huijin Feng, Yuanchao Li, and Bing Zhou. "Rhodium(iii)-catalyzed alkylation of primary C(sp3)–H bonds with α-diazocarbonyl compounds." Chemical Communications 52, no. 62 (2016): 9672–75. http://dx.doi.org/10.1039/c6cc03846h.

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16

Geigle, Stefanie N., Laura A. Wyss, Shana J. Sturla, and Dennis G. Gillingham. "Copper carbenes alkylate guanine chemoselectively through a substrate directed reaction." Chemical Science 8, no. 1 (2017): 499–506. http://dx.doi.org/10.1039/c6sc03502g.

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17

Yu, Sifan, Jinzhou Chen, Gengxin Liu, Jinping Lei, Wenhao Hu, and Huang Qiu. "A gold(i)-catalysed chemoselective three-component reaction between phenols, α-diazocarbonyl compounds and allenamides." Chemical Communications 56, no. 11 (2020): 1649–52. http://dx.doi.org/10.1039/c9cc09470a.

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A gold(i)-catalysed highly chemoselective three-component reaction of phenols, α-diazocarbonyl compounds and allenamides is presented. This transformation features mild reaction conditions, high functional group tolerance, and broad applicability.

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18

Zhou, Minghui, Qin Su, Yesu Addepalli, Yun He, and Zhen Wang. "An asymmetric Mannich reaction of α-diazocarbonyl compounds and N-sulfonyl cyclic ketimines catalyzed by complexes generated from chiral and achiral phosphines with gold(i)." Organic & Biomolecular Chemistry 16, no. 16 (2018): 2923–31. http://dx.doi.org/10.1039/c8ob00577j.

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An unprecedented Lewis acidic gold(i)-complex generated from chiral BINAP and PPh₃AuCl has been developed for the Mannich reaction of α-diazocarbonyl compounds and N-sulfonyl cyclic ketimines.

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19

Chuprun, Sergey, Dmitry Dar’in, Grigory Kantin, and Mikhail Krasavin. "[3+2]-Cycloaddition of α-Diazocarbonyl Compounds with Arenediazonium Salts Catalyzed by Silver Nitrate Delivers 2,5-Disubstituted Tetrazoles." Synthesis 51, no. 21 (August 12, 2019): 3998–4005. http://dx.doi.org/10.1055/s-0039-1690159.

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[3+2]-Cycloaddition of arenediazonium salts with diazo compounds (earlier exemplified only for trimethylsilyldiazomethane and 2,2,2-trifluorodiazoethane) has been developed to include a wide range of readily available α-diazocarbonyl compounds. The resulting 2-aryl-5-acyl-2H-tetrazoles are of high value in medicinal chemistry.

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20

Rao, Changqing, Shaoyu Mai, and Qiuling Song. "Rh(ii)/phosphine-cocatalyzed synthesis of dithioketal derivatives from diazo compounds through simultaneous construction of two different C–S bonds." Chemical Communications 54, no. 47 (2018): 5964–67. http://dx.doi.org/10.1039/c8cc01656a.

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Rhodium(ii)/phosphine-cocatalyzed bis-sulfuration of α-diazocarbonyl compounds using thiosulfonates as the sulfenylating agent, which provided two sulfur-containing moieties, was developed via simultaneous inter- and intra-molecular C–S bond formation.

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21

Aher, Yogesh N., Dhanaji M. Lade, and Amit B. Pawar. "Cp*Ir(iii)-catalyzed C–H/N–H functionalization of sulfoximines for the synthesis of 1,2-benzothiazines at room temperature." Chemical Communications 54, no. 49 (2018): 6288–91. http://dx.doi.org/10.1039/c8cc03288b.

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The first Cp*Ir(iii)-catalyzed C–H/N–H bond functionalization of sulfoximines with α-diazocarbonyl compounds has been developed for the synthesis of 1,2-benzothiazines under redox-neutral conditions at room temperature.

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22

Kidonakis, Marios, and Manolis Stratakis. "Reduction of the Diazo Functionality of α-Diazocarbonyl Compounds into a Methylene Group by NH3BH3 or NaBH4 Catalyzed by Au Nanoparticles." Nanomaterials 11, no. 1 (January 18, 2021): 248. http://dx.doi.org/10.3390/nano11010248.

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Supported Au nanoparticles on TiO2 (1 mol%) are capable of catalyzing the reduction of the carbene-like diazo functionality of α-diazocarbonyl compounds into a methylene group [C=(N2) → CH2] by NH3BH3 or NaBH4 in methanol as solvent. The Au-catalyzed reduction that occurs within a few minutes at room temperature formally requires one hydride equivalent (B-H) and one proton that originates from the protic solvent. This pathway is in contrast to the Pt/CeO2-catalyzed reaction of α-diazocarbonyl compounds with NH3BH3 in methanol, which leads to the corresponding hydrazones instead. Under our stoichiometric Au-catalyzed reaction conditions, the ketone-type carbonyls remain intact, which is in contrast to the uncatalyzed conditions where they are selectively reduced by the boron hydride reagent. It is proposed that the transformation occurs via the formation of chemisorbed carbenes on Au nanoparticles, having proximally activated the boron hydride reagent. This protocol is the first general example of catalytic transfer hydrogenation of the carbene-like α -ketodiazo functionality.

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23

Peng, Cheng, Wei Zhang, Guobing Yan, and Jianbo Wang. "Arylation and Vinylation of α-Diazocarbonyl Compounds with Boroxines." Organic Letters 11, no. 7 (April 2, 2009): 1667–70. http://dx.doi.org/10.1021/ol900362d.

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24

Zhang, Zhenhua, and Jianbo Wang. "Recent studies on the reactions of α-diazocarbonyl compounds." Tetrahedron 64, no. 28 (July 2008): 6577–605. http://dx.doi.org/10.1016/j.tet.2008.04.074.

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25

Elkin, Pavel K., Vitalij V. Levin, Alexander D. Dilman, Marina I. Struchkova, Pavel A. Belyakov, Dmitry E. Arkhipov, Alexander A. Korlyukov, and Vladimir A. Tartakovsky. "Reactions of CF3-substituted boranes with α-diazocarbonyl compounds." Tetrahedron Letters 52, no. 41 (October 2011): 5259–63. http://dx.doi.org/10.1016/j.tetlet.2011.07.141.

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26

Rao, M. V. Krishna, K. Nagarjuna Reddy, B. Sridhar, and B. V. Subba Reddy. "ortho-Alkylation of 2-arylindazoles with α-diazocarbonyl compounds." Tetrahedron Letters 61, no. 35 (August 2020): 152252. http://dx.doi.org/10.1016/j.tetlet.2020.152252.

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27

Solovyev, Igor V., Daniil D. Zhukovsky, Dmitry V. Dar’in, and Mikhail Yu Krasavin. "N-Alkylation of Nitrogen Heterocycles with α-Diazocarbonyl Compounds." Chemistry of Heterocyclic Compounds 56, no. 7 (July 2020): 809–13. http://dx.doi.org/10.1007/s10593-020-02736-y.

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28

Ford, Alan, Hugues Miel, Aoife Ring, Catherine N. Slattery, Anita R. Maguire, and M. Anthony McKervey. "ChemInform Abstract: Modern Organic Synthesis with α-Diazocarbonyl Compounds." ChemInform 46, no. 46 (October 27, 2015): no. http://dx.doi.org/10.1002/chin.201546271.

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29

Ramakrishna, D. S. "Preparation of Novel Chiral α-Diazocarbonyl Compounds Using Regitz’s Methodology." Organic Preparations and Procedures International 54, no. 2 (January 7, 2022): 178–83. http://dx.doi.org/10.1080/00304948.2021.2010466.

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30

Feng, Jiajun, Xiangyan Yi, Yaofeng Fu, Yang Yu, and Fei Huang. "Progress in N-H Insertion Reaction of α-Diazocarbonyl Compounds." Chinese Journal of Organic Chemistry 39, no. 11 (2019): 3013. http://dx.doi.org/10.6023/cjoc201904044.

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31

Zhang, Yan, and Jianbo Wang. "Recent development of reactions with α-diazocarbonyl compounds as nucleophiles." Chemical Communications, no. 36 (2009): 5350. http://dx.doi.org/10.1039/b908378b.

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32

Slattery, Catherine N., Alan Ford, and Anita R. Maguire. "Catalytic asymmetric C–H insertion reactions of α-diazocarbonyl compounds." Tetrahedron 66, no. 34 (August 2010): 6681–705. http://dx.doi.org/10.1016/j.tet.2010.05.073.

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33

Chen, Shufeng, and Jianbo Wang. "Palladium-catalyzed reaction of allyl halides with α-diazocarbonyl compounds." Chemical Communications, no. 35 (2008): 4198. http://dx.doi.org/10.1039/b806970k.

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34

Peng, Cheng, Yan Wang, and Jianbo Wang. "Palladium-Catalyzed Cross-Coupling of α-Diazocarbonyl Compounds with Arylboronic Acids." Journal of the American Chemical Society 130, no. 5 (February 2008): 1566–67. http://dx.doi.org/10.1021/ja0782293.

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35

Koduri, Naga D., Zhiguo Wang, Garrett Cannell, Kate Cooley, Tsebaot Mesfin Lemma, Kun Miao, Michael Nguyen, et al. "Enaminones via Ruthenium-Catalyzed Coupling of Thioamides and α-Diazocarbonyl Compounds." Journal of Organic Chemistry 79, no. 16 (July 31, 2014): 7405–14. http://dx.doi.org/10.1021/jo5011312.

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36

Elkin, Pavel K., Vitalij V. Levin, Alexander D. Dilman, Marina I. Struchkova, Pavel A. Belyakov, Dmitry E. Arkhipov, Alexander A. Korlyukov, and Vladimir A. Tartakovsky. "ChemInform Abstract: Reactions of CF3-Substituted Boranes with α-Diazocarbonyl Compounds." ChemInform 43, no. 4 (December 29, 2011): no. http://dx.doi.org/10.1002/chin.201204156.

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37

Popik, Vladimir V. "The role of molecular geometry in the Wolff rearrangement of α-diazocarbonyl compounds Conformational control or structural constraints?" Canadian Journal of Chemistry 83, no. 9 (September 1, 2005): 1382–90. http://dx.doi.org/10.1139/v05-152.

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Relaxed scans of potential energy surfaces for the loss of nitrogen from four different diazocarbonyl compounds: 3-diazo-2-butanone (1), 2-diazocyclohexanone (2), methyl diazomalonate (3), and diazo Meldrum's acid (4), were conducted at the B3LYP/6-31+G(d,p) level. The geometries of species and transition states involved in the process were optimized at the B3LYP/6-311+G(3df,2p) level, while electronic energies were computed using the MP2(full)/aug-cc-pVTZ method. These calculations suggest that the rigidity of cyclic molecules, rather than the conformational structure of the starting diazocarbonyl compounds, defines the pathway of the dediazotization reaction. In acyclic diazocarbonyl compounds, loss of nitrogen results in the formation of a carbene, which is stabilized by the overlap of the system of carbonyl group and the unshared electron pair of a singlet carbene. On the contrary, in small- to medium-sized cyclic systems, carbonyl carbenes are unable to attain a stabilizing orthogonal conformation. Consequently, cyclic carbonyl carbenes are less stable, and the concerted Wolff rearrangement becomes the predominant process. Transition states for the concerted Wolff rearrangement and for the formation of carbonyl carbenes have a very similar geometry.Key words: diazocarbonyl compounds, Wolff rearrangement, conformation, carbene, ketene.

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38

Semenov, S. G., and M. V. Makarova. "Quantum chemical study of α-diazocarbonyl bullvalene derivatives and related heterocyclic compounds." Russian Journal of Organic Chemistry 50, no. 3 (March 2014): 439–41. http://dx.doi.org/10.1134/s1070428014030245.

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39

Sengupta, Saumitra, and Somnath Mondal. "InCl3: A new Lewis acid catalyst for reactions with α-diazocarbonyl compounds." Tetrahedron Letters 40, no. 49 (December 1999): 8685–88. http://dx.doi.org/10.1016/s0040-4039(99)01843-2.

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40

Kidonakis, Marios, and Manolis Stratakis. "Au Nanoparticle-Catalyzed Insertion of Carbenes from α-Diazocarbonyl Compounds into Hydrosilanes." Organic Letters 20, no. 13 (June 27, 2018): 4086–89. http://dx.doi.org/10.1021/acs.orglett.8b01638.

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41

Austeri, Martina, Diane Rix, Walid Zeghida, and Jérôme Lacour. "CpRu-Catalyzed O−H Insertion and Condensation Reactions of α-Diazocarbonyl Compounds." Organic Letters 13, no. 6 (March 18, 2011): 1394–97. http://dx.doi.org/10.1021/ol2000815.

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42

Yang, Xiaobo, Jiyang Jie, Haoyi Li, and Meihui Piao. "Ir(iii)-catalyzed synthesis of isoquinolines from benzimidates and α-diazocarbonyl compounds." RSC Advances 6, no. 62 (2016): 57371–74. http://dx.doi.org/10.1039/c6ra10045g.

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We report herein a tandem Ir(iii)-catalyzed C–H activation and annulation reactions for the synthesis of isoquinolines. This novel method affords an alternative strategy for the construction of diverse and useful isoquinoline derivatives.

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43

Liu, Lu, and Junliang Zhang. "ChemInform Abstract: Gold-Catalyzed Transformations of α-Diazocarbonyl Compounds: Selectivity and Diversity." ChemInform 47, no. 13 (March 2016): no. http://dx.doi.org/10.1002/chin.201613252.

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44

Slattery, Catherine N., Alan Ford, and Anita R. Maguire. "ChemInform Abstract: Catalytic Asymmetric C-H Insertion Reactions of α-Diazocarbonyl Compounds." ChemInform 41, no. 48 (November 4, 2010): no. http://dx.doi.org/10.1002/chin.201048241.

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45

Alavi, Sima, Jian-Bin Lin, and Huck K. Grover. "Copper-Catalyzed Annulation of Indolyl α-Diazocarbonyl Compounds Leads to Structurally Rearranged Carbazoles." Organic Letters 23, no. 14 (July 1, 2021): 5559–64. http://dx.doi.org/10.1021/acs.orglett.1c01965.

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46

Jabre, Nitinkumar D., and Matthias Brewer. "Stereoelectronic Effects in the Fragmentation of γ-Silyloxy-β-hydroxy-α-diazocarbonyl Compounds." Journal of Organic Chemistry 77, no. 21 (October 15, 2012): 9910–14. http://dx.doi.org/10.1021/jo301944t.

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47

Xu, Feng, Shiwei Zhang, Xiangnan Wu, Yu Liu, Weifeng Shi, and Jianbo Wang. "2,3-Migration in Rh(II)-Catalyzed Reactions of β-Trifluoroacetamido α-Diazocarbonyl Compounds." Organic Letters 8, no. 15 (July 2006): 3207–10. http://dx.doi.org/10.1021/ol061047d.

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48

Hussaini, Syed R., and et al et al. "ChemInform Abstract: Enaminones via Ruthenium-Catalyzed Coupling of Thioamides and α-Diazocarbonyl Compounds." ChemInform 46, no. 7 (January 29, 2015): no. http://dx.doi.org/10.1002/chin.201507065.

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49

Huang, Junmin, Xinwei Hu, Fengjuan Chen, Jiao Gui, and Wei Zeng. "Rhodium(i)-catalyzed vinylation/[2 + 1] carbocyclization of 1,6-enynes with α-diazocarbonyl compounds." Organic & Biomolecular Chemistry 17, no. 29 (2019): 7042–54. http://dx.doi.org/10.1039/c9ob01028a.

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50

West, F. G., Kevin W. Glaeske, and B. N. Naidu. "One-Step Synthesis of Tertiary α-Amino Ketones and α-Amino Esters From Amines and Diazocarbonyl Compounds." Synthesis 1993, no. 10 (1993): 977–80. http://dx.doi.org/10.1055/s-1993-25984.

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