Abstract:
Mesyl azide generated in situ in aqueous medium converted a range of active methylene substrates into the corresponding diazo compounds in good yields and high purity with no need for chromatographic purification. The products thus obtained are suitable for the subsequent RhII-catalyzed O–H insertions with no need for chromatography in the interim.
Keywords:
diazo transfer, sulfonyl azides, in situ generation, mesyl azide, active methylene compounds, aqueous medium.
Citation:
R. Shevalev, P. A. Zhmurov, D. V. Dar'in, M. Yu. Krasavin, “Taking diazo transfer to water: α-diazo carbonyl compounds from in situ generated mesyl azide”, Mendeleev Commun., 30:3 (2020), 372–373
Linking options:
https://www.mathnet.ru/eng/mendc1201
https://www.mathnet.ru/eng/mendc/v30/i3/p372
This publication is cited in the following 2 articles:
D. Zhukovsky, E. V. Kanov, R. R. Gainetdinov, M. Yu. Krasavin, “Synthesis of a library of 2-aryl-2H-tetrazole-5-carboxamides for photoaffinity labeling of aminergic G-protein coupled receptors”, Mendeleev Commun., 32:5 (2022), 604–605
Evgeny Chupakhin, Martha Gecht, Alexander Ivanov, Grigory Kantin, Dmitry Dar'in, Mikhail Krasavin, “(E)-3-Arylidene-4-diazopyrrolidine-2,5-diones: Preparation and Use in RhII-Catalyzed X–H Insertion Reactions towards Novel, Medicinally Important Michael Acceptors”, Synthesis, 53:07 (2021), 1292
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