Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole

Schmidt A, Habeck T, Snovydovych B, Eisfeld W (2007)
ORGANIC LETTERS 9(18): 3515-3518.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Thermal decarboxylation converts 1,2-dimethylindazolium-3-carboxylate into indazol-3-ylidene, which reacts in situ with ketones to form stable 1:1 adducts. When the reaction is conducted with aromatic aldehydes in alcohols, redox esterifications to benzoates are observed. Model reactions such as redox esterifications of aromatic aldehydes with sodium alcoholates in the presence of 1,2-dimethylindazolium salt and oxidations of sodium benzylates by 1,2-dimethylindazolium salt to aldehydes lend support to a Cannizzaro-type mechanism of this reaction.
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ORGANIC LETTERS
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9
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18
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3515-3518
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Schmidt A, Habeck T, Snovydovych B, Eisfeld W. Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS. 2007;9(18):3515-3518.
Schmidt, A., Habeck, T., Snovydovych, B., & Eisfeld, W. (2007). Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS, 9(18), 3515-3518. doi:10.1021/ol0713739
Schmidt, A., Habeck, T., Snovydovych, B., and Eisfeld, W. (2007). Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS 9, 3515-3518.
Schmidt, A., et al., 2007. Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS, 9(18), p 3515-3518.
A. Schmidt, et al., “Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole”, ORGANIC LETTERS, vol. 9, 2007, pp. 3515-3518.
Schmidt, A., Habeck, T., Snovydovych, B., Eisfeld, W.: Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole. ORGANIC LETTERS. 9, 3515-3518 (2007).
Schmidt, Andreas, Habeck, Tobias, Snovydovych, Bohdan, and Eisfeld, Wolfgang. “Addition reactions and redox esterifications of carbonyl compounds by N-Heterocyclic carbenes of indazole”. ORGANIC LETTERS 9.18 (2007): 3515-3518.

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PMID: 29392251
Cross-dehydrogenative coupling for the intermolecular C-O bond formation.
Krylov IB, Vil' VA, Terent'ev AO., Beilstein J Org Chem 11(), 2015
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Dimerisation, rhodium complex formation and rearrangements of N-heterocyclic carbenes of indazoles.
Guan Z, Namyslo JC, Drafz MH, Nieger M, Schmidt A., Beilstein J Org Chem 10(), 2014
PMID: 24778738
Pericyclic rearrangements of N-heterocyclic carbenes of indazole to substituted 9-aminoacridines.
Guan Z, Wiechmann S, Drafz M, Hübner E, Schmidt A., Org Biomol Chem 11(21), 2013
PMID: 23613125
Functionalized 4-aminoquinolines by rearrangement of pyrazole N-heterocyclic carbenes.
Schmidt A, Münster N, Dreger A., Angew Chem Int Ed Engl 49(15), 2010
PMID: 20229542
One-pot oxidative esterification and amidation of aldehydes.
Ekoue-Kovi K, Wolf C., Chemistry 14(21), 2008
PMID: 18523938

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